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  • 1. Aili, Daniel
    et al.
    Enander, Karin
    Rydberg, Johan
    Lundström, Ingemar
    Baltzer, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Liedberg, Bo
    Aggregation-Induced Folding of a de novo Designed Polypeptide Immobilized on Gold Nanoparticles2006In: J. Am. Chem. Soc., no 128, p. 2194-2195Article in journal (Refereed)
  • 2. Aili, Daniel
    et al.
    Enander, Karin
    Rydberg, Johan
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Nesterenko, Irina
    Björefors, Fredrik
    Baltzer, Lars
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Liedberg, Bo
    Folding Induced Assembly of Polypeptide Decorated Gold Nanoparticles2008In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 130, no 17, p. 5780-5788Article in journal (Refereed)
    Abstract [en]

    Reversible assembly of gold nanoparticles controlled by the homodimerization and folding of an immobilized de novo designed synthetic polypeptide is described. In solution at neutral pH, the polypeptide folds into a helix-loop-helix four-helix bundle in the presence of zinc ions. When immobilized on gold nanoparticles, the addition of zinc ions induces dimerization and folding between peptide monomers located on separate particles, resulting in rapid particle aggregation. The particles can be completely redispersed by removal of the zinc ions from the peptide upon addition of EDTA. Calcium ions, which do not induce folding in solution, have no effect on the stability of the peptide decorated particles. The contribution from folding on particle assembly was further determined utilizing a reference peptide with the same primary sequence but containing both D and L amino acids. Particles functionalized with the reference peptide do not aggregate, as the peptides are unable to fold. The two peptides, linked to the nanoparticle surface via a cysteine residue located in the loop region, form submonolayers on planar gold with comparable properties regarding surface density, orientation, and ability to interact with zinc ions. These results demonstrate that nanoparticle assembly can be induced, controlled, and to some extent tuned, by exploiting specific molecular interactions involved in polypeptide folding.

  • 3. Andersson, Theresa
    et al.
    Lundquist, Martin
    Dolphin, Gunnar T.
    Enander, Karin
    Jonsson, Bengt-Harald
    Nilsson, Jonas W.
    Baltzer, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Cooperative binding of human Carbonic Anhydrase II by functionalized folded polypeptide receptors2005In: Chem. Biol., no 12, p. 1245-1252Article in journal (Refereed)
  • 4.
    Arvidsson, Per
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Ryder, N
    Weiss, M
    Gross, G
    Kretz, O
    Woessner, R
    Seebach, D
    Antibiotic and Hemolytic Activity of a B2/B3 Peptide Capable of Folding into a 12/10-Helical Secondary Structure2003In: ChemBioChem, no 4, p. 1345-1347Article in journal (Refereed)
  • 5.
    Baltzer, Lars
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Polypeptide Conjugate Binders for Protein Recognition2007In: Topics in current chemistry, ISSN 0340-1022, E-ISSN 1436-5049, Vol. 277, p. 89-106Article, review/survey (Refereed)
    Abstract [en]

    A new class of hybrid molecules for protein recognition is presented, where polypeptides are covalently linked to small organic molecules to form polypeptide conjugates that bind proteins with high affinity and selectivity. To illustrate the concept, a binder for human carbonic anhydrase 11 with a dissociation constant of 4 nM is described. The affinity of the polypeptide conjugate arises from cooperativity in binding between a benzenesulfonamide residue, with a dissociation constant of 1.5 mu M, and the polypeptide scaffold with a dissociation constant of < 1 mM. The combination of a ligand with moderate affinity for a target protein with a polypeptide relaxes considerably the need for high affinity on the part of the polypeptide, and thus the need for structural complexity and preorganization. At the same time, the requirement for high affinity on the part of ligand is relaxed. As a consequence, the time for development of robust, high affinity, selective binder is shortened. The chemical approach to protein recognition provides well-defined molecular entities that are conveniently handled, stored and site-specifically functionalized.

  • 6.
    Baltzer, Lars
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    DeGrado, W. F.
    Engineering and design: Expanding the protein world2004In: Editorial overview Current Opinion of Structural Biology, Vol. 14, p. 455-457Article, review/survey (Other (popular scientific, debate etc.))
  • 7.
    Baltzer, Lars
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Klinman, J.P.
    Hynes, J.T.
    Limbach, H-H.
    Acid base catalysis in designed polypeptides2006In: Handbook of Hydrogen Transfer, Wiley , 2006Chapter in book (Refereed)
  • 8. Beletskaya, I.P
    et al.
    Bregadze, V.I.
    Ivushkin, V.A.
    Petrovskii, P.V.
    Sivaev, I.B.
    Sjöberg, Stefan
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Zhigareva, G.B.
    New B-substituted derivatives of m-carborane, p-carborane, and cobalt bis(1,2-decarbollide) anion2004In: J. Organomet. Chem., no 689, p. 2920-Article in journal (Refereed)
  • 9.
    Bergson, Göran
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Linderberg, Jan
    Is a Proposed Reaction Mechanism Free from Unnecessary Assumptions?: Occam's Razor Applied in a Mathematical Way To Complex First-Order Reaction Systems2008In: Journal of Physical Chemistry A, ISSN 1089-5639, E-ISSN 1520-5215, no 112, p. 4235-4240Article in journal (Refereed)
    Abstract [en]

    Following Occam's principle, a proposed reaction mechanism should not contain assumptions about the existence of reactive intermediates and reaction paths that are unnecessary for a full description and interpretation of the available facts. A mechanism refers, in this paper, to a proposed reaction scheme or network that represents the reactions supposed to be going on in a complex reaction system with observable species as well as unobservable reactive intermediates. The scope is limited here to (pseudo) first-order reactions and the steady-state approximation is invoked in order to relate unknown mechanistic rate constants to experimentally determined ones, and, when available, theoretically calculated quantities. When the resulting, nonlinear system of equations admits a unique solution within a physically reasonable domain, it is concluded that the reaction mechanism fulfills Occam's principle. Otherwise, there are many or no solutions. No subjective or qualitative arguments enter the procedure and the outcome is not negotiable.

  • 10. Blixt, Ola
    et al.
    Hoffmann, Julia
    Svensson, Stefan
    Norberg, Thomas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Pathogen specific carbohydrate antigen microarrays: a chip for detection of Salmonella O-antigen specific antibodies2008In: Glycoconjugate Journal, ISSN 0282-0080, E-ISSN 1573-4986, Vol. 25, no 1, p. 27-36Article in journal (Refereed)
    Abstract [en]

    A Salmonella O-antigen microarray was developed by covalent coupling of oligosaccharide antigens specific for serogroups Salmonella enterica sv. Paratyphi (group A), Typhimurium (group B) and Enteritidis (group D). Antibodies were correctly detected in sera from patients with culture verified salmonellosis. High serogroup-specificity was seen with the disaccharide antigens. With the larger antigens, containing the backbone sequence Man alpha 1-2Rha alpha 1-2Gal (MRG), common backbone-specific antibodies (O-antigen 12) were also detected. This is "proof of principle" that pathogen-specific carbohydrate antigen microarrays constitute a novel technology for rapid and specific serological diagnosis in either individual patients or larger sero-epidemiological and vaccine studies.

  • 11.
    Bruskin, Alexander
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Sivaev, Igor
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Persson, Mikael
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Lundqvist, Hans
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Carlsson, Jörgen
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Sjöberg, Stefan
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Tolmachev, Vladimir
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Radiobromination of monoclonal antibody using potassium [76Br] (4 isothiocyanatobenzyl-ammonio)-bromo-decahydro-closo-dodecaborate (Bromo-DABI)2004In: Nuclear Medicine and Biology, ISSN 0969-8051, E-ISSN 1872-9614, Vol. 31, no 2, p. 205-11Article in journal (Refereed)
    Abstract [en]

    The use of charged linkers in attaching radiohalogens to tumor-seeking biomolecules may improve intracellular retention of the radioactive label after internalization and degradation of targeting proteins. Derivatives of polyhedral boron clusters, such as closo-dodecaborate (2-) anion, might be possible charged linkers. In this study, a bifunctional derivative of closo-dodecaborate, (4-isothiocyanatobenzyl-ammonio)-undecahydro-closo-dodecaborate (DABI) was labeled with positron-emitting nuclide (76)Br (T 1/2 = 16.2 h) and coupled to anti-HER2/neu humanized antibody Trastuzumab. The overall labeling yield at optimized conditions was 80.7 +/- 0.6%. The label was proven to be stable in vitro in physiological and a set of denaturing conditions. The labeled antibody retained its capacity to bind to HER-2/neu antigen expressing cells. The results of the study demonstrated feasibility for using derivatives of closo-dodecaborate in indirect labeling of antibodies for radioimmunoPET.

  • 12.
    Chajara, Khalil
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Ottosson, Henrik
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    An improved pathway to 6,6-disubstituted fulvenes2004In: Tetrahedron Letters, no 45, p. 6741-6744Article in journal (Refereed)
    Abstract [en]

    Pentafulvenes with alkyl and/or aryl substituents at the exocyclic position are formed rapidly in high yields through reaction of crystalline sodium cyclopentadienide directly with the appropriate ketones.

  • 13. Dybala-Defratyka, Agnieszka
    et al.
    Rostkowski, Michal
    Matsson, Olle
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Westaway, Kenneth C.
    Paneth, Piotr
    A New Interpretation of Chlorine Leaving Group Kinetic Isotope Effects; A Theoretical Approach2004In: J. Org. Chem., Vol. 69, p. 4900-4905Article in journal (Refereed)
    Abstract [en]

    The chlorine leaving group kinetic isotope effects (KIEs) for the SN2 reactions between methyl chloride and a wide range of anionic, neutral, and radical anion nucleophiles were calculated in the gas phase and, in several cases, using a continuum solvent model. In contrast to the expected linear dependence of the chlorine KIEs on the Ca-CI bond order in the transition state, the KIEs fell in a very small range (1.0056-1.0091), even though the Ca-CI transition state bond orders varied widely from approximately 0.32 to 0.78, a range from reactant-like to very product-like. This renders chlorine KIEs, and possibly other leaving-group KIEs, less useful for studies of reaction mechanisms than commonly assumed. A partial explanation for this unexpected relationship between the Ca-CI transition state bond order and the magnitude of the chlorine KIE is presented.

  • 14. Enander, Karin
    et al.
    Aili, D.
    Baltzer, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Lundström, I.
    Liedberg, B.
    Alpha helix-inducing dimerization of synthetic plypeptide scaffolds on gold2005In: Langmuir, no 21, p. 2480-2487Article in journal (Refereed)
  • 15. Enander, Karin
    et al.
    Aili, D.
    Baltzer, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Lundström, I.
    Liedberg, B.
    Alpha helix-inducing dimerization of synthetic polypeptide scaffolds on gold2005In: Langmuir, no 21, p. 2480-2487Article in journal (Refereed)
  • 16.
    Enander, Karin
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Dolphin, G. T.
    Baltzer, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Designed functionalized helix-loop-helix motifs that bind human Carbonic Anhydrase II- a new class of synthetic receptor molecules2004In: J. Am. Chem. Soc., no 126, p. 4464-4465Article in journal (Refereed)
  • 17.
    Enander, Karin
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Dolphin, G.T.
    Liedberg, B.
    Lundström, I.
    Baltzer, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    A versatile polypeptide platform for intergrated recognition and reporting - affinity arrays for protein - ligand interaction analysis2004In: Chem. Eur. J., no 10, p. 2375-2385Article in journal (Refereed)
  • 18. Enander, Karin
    et al.
    Dolphin, Gunnar T.
    Baltzer, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Designed, functionalized helix-loop-helix motifs that bind human Carbonic Anhydrase II - a new class of synthetic receptor molecules2004In: J. Am. Chem. Soc., no 126, p. 4464-4465Article in journal (Refereed)
  • 19. Enander, Karin
    et al.
    Dolphin, Gunnar T.
    Liedberg, Bo
    Lundström, Ingemar
    Baltzer, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    A versatile polypeptide platform for integrated recognition and reporting - affinity arrays for protein-ligand interaction2004In: Chem. Eur. J., no 10, p. 2375-2385Article in journal (Refereed)
  • 20.
    Erlandsson, Maria
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Karimi, Farhad
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Takahashi, Kayo
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Långström, Bengt
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    18F-Labelled vorozole analogues as PET tracer for aromatase2008In: J. Label Compd Radiopharm, no 51, p. 207-212Article in journal (Refereed)
  • 21. Fang, Yao-ren
    et al.
    MacMillar, Susanna
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Eriksson, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Kolodziejska-Huben, Magdalena
    Dybala-Defratyka, Agnieszka
    Paneth, Piotr
    Matsson, Olle
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Westaway, Kenneth Charles
    The Effect of Solvent on the Structure of the Transition State for the SN2 Reaction between Cyanide Ion and Ethyl Chloride in DMSO and THF Probed with Six Different Kinetic Isotope Effects2006In: J. Org. Chem, no 71, p. 4742-4747Article in journal (Refereed)
    Abstract [en]

    The secondary a- and B-deuterium, the a-carbon, the nucleophile carbon, the nucleophile nitrogen, and the chlorine leaving group kinetic isotope effects forthe SN2 reaction between cyanide ion an dethyl chloride were determined in the very slightly polar solvent THF at 30 C. A comparison of these KIEs with those reported earlier for the same reaction in the polar solvent DMSO shows that the transition state in THF is only sligthly tighter with very slightly shorter NC-Ca-CI bonds. This minor change in transition state structure does not account for the different transition structures that were earlier suggested by interpreting the experimental KIEs and the gas-phase calculations, respectively. It therefore seems unlikely that the different transition states suggested by the two methods are due to the lack of appropriate solvent modeling in the theoretical calculations. Previously it was predicted that the transition state of SN2 reactions where the nucleophile and the leaving group have the same charge would be unaffected by a charge in solvent. The experimental KIEs support this view.

  • 22. Forngren, Tobias
    et al.
    Samuelsson, Linda
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Långström, Bengt
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    A 11C-methylstannane (5-[11C]methyl-1-aza-5-stannabicyclo[3.3.3] undecane) for use in palladium-mediated [11C]C-Cbond forming reactions with organic halides2004In: J. Labelled Compd. Rad., no 47, p. 71-78Article in journal (Refereed)
  • 23. Frank, Richard A.
    et al.
    Långström, Bengt
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Antoni, Gunnar
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Montalto, Michael C.
    Agdeppa, Eric D.
    Mendizabal, Marivi
    Wilson, Ian A.
    Vanderheyden, Jean-Luc
    The Imaging Continuum: Bench to Biomarkers to Diagnostics2007In: Journal of labelled compounds & radiopharmaceuticals, ISSN 0362-4803, E-ISSN 1099-1344, Vol. 50, no 9-10, p. 746-769Article, review/survey (Refereed)
    Abstract [en]

    Innovation in basic and applied science has brought radiotracers to fruition as diagnostics. Non-invasive, longitudinal, and quantifiable molecular imaging is the key to diagnosing and monitoring numerous illnesses, with more to come from characterization of the clinical relevance of findings from genomics research. Radiotracers enable real-time in vivo studies of the effects of drug candidates on receptors, pathways, pharmacodynamics, and clinically relevant endpoints, thereby providing both early detection of pathophysiology to enable early intervention, and then monitoring of treatment responses to enable individualization of treatment regimens. We review developments which have translated imaging from bench to bedside, or biomarkers to diagnostics. Notable developments include (1) synthesis methods for rapid 11C labeling of biomolecules to high specific radioactivity; (2) ligand-binding assays for screening molecular imaging agents rather than drugs; (3) in vivo imaging of radiotracers in animals; (4) discovering the imaging advantages of 99mTc, 11C, and 18F; (5) co-registration and automated quantitative assessment of high spatial resolution CT and MR images with molecular images from PET for longitudinal studies of treatment effect.

  • 24.
    Ghirmai, Senait
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Mume, Eskender
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Lundqvist, Hans
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Tolmachev, Vladimir
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Sjöberg, Stefan
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Synthesis and radioiodination of some 9-aminoacridine derivatives for potential use in radionuclide therapy2005In: Journal of labelled compounds & radiopharmaceuticals, ISSN 0362-4803, E-ISSN 1099-1344, Vol. 48, no 12, p. 855-871Article in journal (Refereed)
  • 25. Hederos, Sofia
    et al.
    Baltzer, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Nucleophile selectivity in the enzyme catalyzed acyl transfer reaction of a thiol ester2005In: Biopolymers, no 79, p. 292-299Article in journal (Refereed)
  • 26. Hederos, Sofia
    et al.
    Broo, Kerstin
    Jakobsson, Emma
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Faculty of Science and Technology, Biology, Department of Cell and Molecular Biology. Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Biochemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Faculty of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
    Kleywegt, Gerard J
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Faculty of Science and Technology, Biology, Department of Cell and Molecular Biology. Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Biochemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Faculty of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
    Mannervik, Bengt
    Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Biochemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Faculty of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
    Baltzer, Lars
    Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Biochemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Faculty of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
    A new enzyme by rational design - the incorporation of a single His residue enables efficient thioester hydrolysis by human glutathione transferase A1-12004In: Proc. Nat. Acad. Sci., Vol. 101, p. 13163-13167Article in journal (Refereed)
    Abstract [en]

    A strategy for rational enzyme design is reported and illustrated by the engineering of a protein catalyst for thiol-ester hydrolysis. Five mutants of human glutathione (GSH; gamma-Glu-Cys-Gly) transferase A1-1 were designed in the search for a catalyst and to provide a set of proteins from which the reaction mechanism could be elucidated. The single mutant A216H catalyzed the hydrolysis of the S-benzoyl ester of GSH under turnover conditions with a k(cat)/K(M) of 156 M(-1) x min(-1), and a catalytic proficiency of >10(7) M(-1) when compared with the first-order rate constant of the uncatalyzed reaction. The wild-type enzyme did not hydrolyze the substrate, and thus, the introduction of a single histidine residue transformed the wild-type enzyme into a turnover system for thiol-ester hydrolysis. By kinetic analysis of single, double, and triple mutants, as well as from studies of reaction products, it was established that the enzyme A216H catalyzes the hydrolysis of the thiol-ester substrate by a mechanism that includes an acyl intermediate at the side chain of Y9. Kinetic measurements and the crystal structure of the A216H GSH complex provided compelling evidence that H216 acts as a general-base catalyst. The introduction of a single His residue into human GSH transferase A1-1 created an unprecedented enzymatic function, suggesting a strategy that may be of broad applicability in the design of new enzymes. The protein catalyst has the hallmarks of a native enzyme and is expected to catalyze various hydrolytic, as well as transesterification, reactions.

  • 27.
    Itsenko, Oleksiy
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Kihlberg, Tor
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Långström, Bengt
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Carboxylation of Alkyl Iodides with [11C] and (13C)Carbon Monoxide: Using Sulfoxides as Oxygen Nucleophiles2005In: Synlett, no 20, p. 3154-3156Article in journal (Refereed)
    Abstract [en]

    11C-Labeled carboxylic acids were prepared from alkyl iodides and [11C]carbon monoxide by irradiation by UV light in anhydrous DMSO solutions in the presence of triethylamine. Sulfoxides other than DMSO can be used and may be used in stoichiometric amounts using inert solvents.

  • 28.
    Itsenko, Oleksiy
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Kihlberg, Tor
    Långström, Bengt
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Labeling of aliphatic carboxylic acids using [11C]carbon monoxide2006In: Nature Protocols, ISSN 1754-2189, Vol. 1, no 2, p. 798-802Article in journal (Refereed)
    Abstract [en]

    Here we present a protocol for labeling aliphatic carboxylic acids with the positron-emitting radionuclide 11C (t1/2 = 20.4 min) at the carboxyl position using [11C]carbon monoxide via photoinitiated free radical-mediated carbonylation. A solution of an alkyl iodide in a homogenous binary organic solvent-water mixture is introduced into a high-pressure photochemical reactor containing [11C]carbon monoxide. Then the reactor contents are pressurized to 40 MPa and irradiated with ultraviolet light for 6 min. The labeled product is purified using HPLC. All manipulations with radioactivity including the labeling synthesis are carried out on an automated Synthia system. In a typical case, 3.19 GBq of purified [1-11C]1,10-decanedicarboxylic acid (with a specific radioactivity of 188 GBq/μmol) can be obtained within 35 min after the end of a 10-μAh bombardment. Compared to previous labeling methods, this protocol is compatible with a wider range of functional groups, utilizes less-sensitive precursors, and is less subject to isotopic dilution.

  • 29.
    Itsenko, Oleksiy
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Kihlberg, Tor
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Långström, Bengt
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Photoinitiated Carbonylation with [11C]Carbon Monoxide Using Amines and Alkyl Iodides2004In: J. Org. Chem., no 69, p. 4356-4360Article in journal (Refereed)
  • 30.
    Itsenko, Oleksiy
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Kihlberg, Tor
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Långström, Bengt
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Synthesis of Aliphatic [carbony.-11C]Esters Using [11C]Carbon Monoxide2005In: Eur. J. Org. Chem., p. 3830-3834Article in journal (Refereed)
    Abstract [en]

    Aliphatic esters were labelled with a short-lived radionuclide,11C with t½=20.3 min, at the carbonyl position using [11C]carbon monoxide via rapid (6 min) photoinduced radical-mediated carbonylation reactions. The esters were prepared from primary, secondary, and tertiary alkyl iodides, and various alcohols, including tert-butyl alcohol and phenol. The use of strong bases was necessary to achieve good radiochemical yields in short reaction time. Isolated decay-corrected radiochemical yields were in the range of 40-68%. For example, methyl hydrogen dodecanoate was labelled at the ester carbonyl in 61% isolated decay-corrected radiochemical yield with a specific radioactivity of 158 GBq/umol within approcimately 25 min of the production of [11C]carbon monoxide. Two (13C]substituted esters were synthesised using this method to verify the labelling position.

  • 31.
    Itsenko, Oleksiy
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Långström, Bengt
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Photoinitiaed Free Radical Carbonylation Enhanced by Photosensitizers2005In: Organic Letters, Vol. 7, no 21, p. 4661-4664Article in journal (Refereed)
    Abstract [en]

    The enchanicing effect of several photsensitizers in photoinitiated radical carbonylation is demonstrated and applied to acceleate the synthesis of compounds labeled with short-lived 11C. With the sensitizers, the synthesis of [carbonyl-11C]esters and acids from alkyl iodides, [11C]carbon monoxides, alcohols, and water provided up to 75-85% decay-corrected radiochemical yields in 6-min reactions under mild conditions. Acetone was used as a sensitier in preparing 13C-substituted 1,10-decanedicarboxylic acid from (13C)carbon monoxide.

  • 32.
    Itsenko, Oleksiy
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Långström, Bengt
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Radical-Mediated Carboxylation of Alkyl iodides with [11C]Carbon Monoxide in Solvent Mixtures2005In: J. Org. Chem, no 70, p. 2244-2249Article in journal (Refereed)
    Abstract [en]

    [carboxyl-11C]Carboxylic acids were prepared from alkyl iodides via photoinitiated radical reactions using 10-8 mol of [11C]carbon monoxide in binary and ternary homogeneous solvent mixtures. Short-(isobutyric), medium-, and long-chain saturated fatty acids (heptadecanoic) were labeled with isolated decay-corrected radiochemical yields ranging from 55% to 70% in 5-7 min reactions. The conversion of [11C]carbon monoxide to products reached 80-90%. To obtain good yields in the reactions performed in water- acetonitrile and water-THF mixtures, the addition of tetrabut-ylammonium hydroxide or potassium hydroxide was essential. The carboxylation was efficient for primary and secondary alkyl iodides. The carboxylation of tertiary iodides was feasible for 1-iodoadamantane but not for tert-butyl iodide. The dependence of the radiochemical yields on reaction time, photoirradiation conditions, and organic and inorganic additives was studied. The method provides a one-step route to [carboxyl-11C]carboxylic acids; traditional methods, in contrast, would require several steps. For example, using the devised reaction, conditions, 3.19 GBq of purified [1-11C]1,10-decanedicarboxylic acid (specific radioactivity 188 GBq/umol) was obtained within 35 min of the end of 10 uAh bombardment. (1-13C)4-Phenylbutyric acid was synthesized using (13C)-carbon monoxide for identifying the labelling position with 1H and 13C NMR.

  • 33.
    Karimi, Farhad
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Erlandsson, Maria
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Lindhe, Örjan
    Medicinska vetenskapsområdet, Faculty of Medicine, Department of Medical Sciences. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Endokrin tumörbiologi.
    Långström, Bengt
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Synthesis of 11C-labelled metomidate analogues as adrenocortical imaging agents2008In: J. Label Compd Radiopharm, no 51, p. 273-276Article in journal (Refereed)
  • 34.
    Kato, Haruhisa
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Brink, Maria
    Möllerstedt, Helene
    Piqueras, Mari Carmen
    Crespo, Raül
    Ottosson, Henrik
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    J. Org. Chem.2005In: J. Org. Chem., no 70, p. 9495-9504Article in journal (Refereed)
  • 35. Kirilovas, D
    et al.
    Naessen, T
    Bergström, M
    Petterman, E
    Carlström, K
    Långström, Bengt
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Characterisation of 11C-vorozole in ovarain tissue in rats throughout wstrous cycle in association with conversion of androgens to estrogens in vivo and in vitro2003In: Steroids, no 68, p. 1139-1146Article in journal (Refereed)
  • 36. Kirolovas, D
    et al.
    Naessen, T
    Bergström, M
    Bonasera, T.A
    Bergström-Petterman, E
    Holte, J
    Carlström, K
    Simberg, N
    Långström, Bengt
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Effects of androgens on aromatase activity and 11C-voroxole binding in grnulosa cells in vitro2003In: Acta Obstet. Gynecol. Scand., no 82, p. 209-215Article in journal (Refereed)
  • 37. Kullberg, E-B.
    et al.
    Stenerlöw, B.
    Ghirmait, Senait
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Lundqvist, Hans
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Malmström, P-U.
    Orlova, Anna
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Tolmachev, Vladimir
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Gedda, L.
    An Aminoacridine Derivative for Radionuclide Therapy: Dna-Binding Properties Studied in a Novel Cell-Free in vitro Assay2005In: Int. J. Onc., no 27, p. 1355-1360Article in journal (Refereed)
  • 38.
    Lindgren, N. Johan V.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Varedian, Miranda
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Photochemical Regulation of an Artificial Hydrolase by a Backbone Incorporated Tertiary Structure Switch2009In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 2, p. 501-505Article in journal (Refereed)
    Abstract [en]

    A stilbene chromophore has been incorporated into the turn region of a 42 amino acid peptide, linking two helical peptide sections. Spatial proximity between these sections, as well as aggregation into dimers, is required to facilitate the catalytic function of this artificial hydrolase. Photomodulation of the hydrolase activity results in an increase of the activity of 42 % upon switching from the trans to the cis isomer of the chromophore. This is rationalized by a change in the aggregation state of the peptidomimetic, which is supported by diffusion coefficients obtained from PFG-NMR experiments. The results show that incorporation of a small, relatively flexible chromophore into a large peptide is capable of inducing a considerable change in tertiary structure and thus, functionality.

  • 39. Lu, L
    et al.
    Samuelsson, Linda
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Bergström, M
    Sato, K
    Fasth, K.J.
    Långström, Bengt
    Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Rat studies comparing 11C-FMAU, 18F-FLT and 76Br-BFU as profileration markers2002In: J. Nuc. Med, no 43, p. 1688-1698Article in journal (Refereed)
  • 40.
    Matsson, Olle
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Isotope Effects for Exotic Nuclei2006In: Isotope Effects in Chemistry and Biology, CRC Press, Taylor & Francis Group, NW , 2006, p. 417-431Chapter in book (Refereed)
  • 41.
    Matsson, Olle
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Dybala-Defratyka, A.
    Rostkowski, M.
    Paneth, P.
    Westaway, K.C.
    A Theoretical Ivnestigation of a-Carbon Kinetic Isotope Effects and Their Relationship to the Transition-State Structure of SN2 Reactions2005In: J. Org. Chem., no 70, p. 4022-4027Article in journal (Refereed)
    Abstract [en]

    The transition structures and a-carbon 12C/13C kinetic isotope for 22 SN2 reactions between methyl chloride and a wide variety of nucleophiles have been calculated using the B1LYP/aug-cc-pVDZ level of theory. Anionic, neutral, and radical anion nucleophiles were used to give a wide range of SN2 transition states so the relationship between the magnitude of the a-carbon kinetic isotope effect and trasition-state structure could be determined. The results suggest that the a-carbon 12C/13C kinetic isotope effects for SN2 reactions will be large (near the experimental maximum) and that the curve relating the magnitude of the KIE to the percent transfer of the a-carbon from the nucleophile to the leaving group in the transition state has a broad maximum. This means very similar KIEs will be found for early, symmetric, and late transition states and that one cannot use the magnitude of these KIEs to estimate transition-state structure.

  • 42.
    Mume, Eskender
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Orlova, Anna
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology.
    Larsson, Barbro
    Nilsson, Ann-Sofie
    Nilsson, Fredrik Y.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Sjöberg, Stefan
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Tolmachev, Vladimir
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology.
    Evaluation of ((4-Hydroxyphenyl)ethyl)maleimide for Site-Specific Radiobromination of Anti-HER2 Affibody2005In: Bioconjugate chemistry, ISSN 1043-1802, E-ISSN 1520-4812, Vol. 16, no 6, p. 1547-1555Article in journal (Refereed)
    Abstract [en]

    Affibody molecules are a new class of small phage-display selected proteins using a scaffold domain of the bacterial receptor protein A. They can be selected for specific binding to a large variety of protein targets. An affibody molecule binidng with high affinity to a tumor antigen HER2 was recently developed for radionuclide diagnostics and therapy in vivo. The use of hte positron-emitting nuclide 76Br(T½ = 16.2 h) could imporve the sensitivity of detection of HER2-expressing tumors. A site-specific radiobromination o fa cysteine-containing variant of the anti-HER2 affibody, (ZHER2:4)2-Cys, using ((4-hydroxpyphenyl)ethyl)maleimide (HPEM), was evaluated in this study. It was found that HPEM can be radiobrominated with an efficiency of 83+0.4% and thereafter coupled to freshly reduced conjugate to exceed 97%. The label was stable against challenge with large excess of nonlabeled bromide and in a high molar strengt solution. In vitro cell tests demonstraded that radiobrominated affibody binds specifically to the HER2-expressing cel-line, SK-OV-3. Biodistribution studies in nude mice bearing SK-OV-3 xenografts have shown tumor accumulation of 4.8 ? 2.2% IA/g and good tumor-to-normal tissue ratios.

  • 43. Naeslund, Charlotta
    et al.
    Ghiramai, Senait
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Sjöberg, Stefan
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Enantioselective synthesis of m-carboranylalanine, a boron-rich analogue of phenylalanine2005In: Tetrahedron, Vol. 61, p. 1181-1186Article in journal (Refereed)
    Abstract [en]

    The enantiomers of the highly lipophilic a-amino acid m-carboranyl-alanine [3-(1.7-dicarba-closo-dodecaborane(12)-1-yl)-2-aminopropanoic acid], a carborane containing analogue of phenylalanine, have been synthesised via hydroxyamination of the N-acyl derivative formed from 3-(m-carboranyl)propionoic acid [3-(1.7-dicarba-closo-dodeca-borane(12)-1-yl)-2-propanoic acid] and Oppolzer's camphor sultam. The enantiomeric excess of both enantiomers of the amino acid was >98%. (S)-Configuration was assigned to the (+)-enantiomer (ch3Oh, 589 nm).

  • 44.
    Norberg, Thomas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Synthesis of phosphodiester-linked microbial polysaccharide structures2009In: Progress in the synthesis of complex carbohydrate chains of plant and microbial polysaccharides / [ed] N. E. Nifantiev, Trivandrum: Transworld Research Network , 2009, p. 309-325Chapter in book (Other academic)
    Abstract [en]

    This chapter reviews work published until mid-2008 on the synthesis of phosphodiester-linked microbial polysaccharide structures, with emphasis on the development during the last two decades. Different techniques and chemistries that have been used to create the phosphodiester linkages are discussed, and syntheses of oligomeric (2-10 repeating units) phosphodiester-linked fragments of natural polysaccharides from different sources are presented.

  • 45.
    Ottosson, Henrik
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Steel, Patrick G.
    Silylenes, Silenes, and Disilenes: Novel Silicon-Based Reagents for Organic Synthesis?2006In: Chem. Eur. J., no 12, p. 1576-1585Article in journal (Refereed)
  • 46. Peter, K.
    et al.
    Nilsson, R.
    Rydberg, J.
    Baltzer, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Inganäs, O.
    Twisting macromolecular chains - self-assembly of a chiral supermolecule from non-chiral polythiophene polyanions and random coil synthetic peptides2004In: Proc. Nat. Acad.Sci, Vol. 101, p. 11197-11202Article in journal (Refereed)
  • 47. Peter, K.
    et al.
    Nilsson, R.
    Rydberg, Johan
    Baltzer, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Inganäs, Olle
    Twisting macromolecular chains-self-assembly of a chiral supermolecule from non-chiral polythiophene polyanions and random coil synthetic peptides2004In: Proc. Nat. Acad. Sci., no 101, p. 11197-11202Article in journal (Refereed)
  • 48.
    Qiu, Wenjun
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Microsystems Technology.
    Sun, Xiaojiao
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Hjort, Klas
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Microsystems Technology.
    Wu, Zhigang
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Microsystems Technology.
    Investigation of the interaction between embedded amphiphilic molecules and PDMS matrix in aqueous environment and their impact on surface2013In: MME 2013 24th Micromechanics and Microsystems Europe Conference, 2013Conference paper (Refereed)
    Abstract [en]

    In this paper, we are the first to investigate systematically how the embedded molecules interact with PDMS matrix in aqueous environments and their impacts on the surface performance by varying various processing conditions such as water exposure time, curing master materials and embedded amphiphilic molecules. The results indicate that the interaction is strongly influenced by various processing conditions in a complicated way and the dominant forces are quite different in various conditions. Among them, water exposure time plays a clearly important role during the process.

  • 49.
    Rahman, Obaidur
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Kihlberg, T.
    Långström, Bengt
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Synthesis of [11C]/(13C) amines via carbonylation followed by reductive amination2004In: Organic & Biomolecular Chemistry, no 2, p. 1612-1616Article in journal (Refereed)
  • 50.
    Rahman, Obaidur
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Kihlberg, Tor
    Långström, Bengt
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
    Synthesis of 11C-/13C-Ketones by Suzuki Coupling2004In: Eur. J. Org. Chem., p. 474-478Article in journal (Refereed)
    Abstract [en]

    Aryl triflates, methyl- or arylboronic acids, and a low concentration of [11C]carbon monoxide were employed on small scale in the syntheses of fifteen 11C-labelled ketones using palladium-mediated Suzuki coupling reactions. The reagents were confined in a micro-autoclave and heated at 150C for 5 min. The reaction required the presence of LiBr, but no additional base. The 11C-labelled products were obtained with decay-corrected radiochemical yields in the range 10-70% and with high specific radioactivity (150-640 GBq/umol). The radiochemical purity of the final products exceeded 98%. One 13C-substituted ketone ([13C]-2'-benzonaphthone)was prepared and analysed by NMR spectroscopy for confirmation of the labelling position. The reference compound 2'-benzonaphthone was prepared by a palldium-catalysed reaction between sodium tetraphenylborate and 2-naphthoyl chloride. 2-Thienyl p-tolyl ketone, 4-nitrophenyl 2-thienyl ketone an d2-naphthyl 2-thienyl ketone were prepared by reactions between thiophene-2-boronic acid and the corresponding acid chlorides. The presented approach is novel and seems to be an efficient method for the synthesis of a wide range of 11C- as well as 13C-labelled ketones.

12 1 - 50 of 67
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