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  • 1. Aili, Daniel
    et al.
    Enander, Karin
    Baltzer, Lars
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Liedberg, Bo
    Synthetic de novo designed polypeptides for control of nanoparticle assembly and biosensing2007In: Biochemical Society Transactions, ISSN 0300-5127, E-ISSN 1470-8752, Vol. 35, no 3, p. 532-534Article in journal (Refereed)
    Abstract [en]

    This contribution describes how de novo designed synthetic helix–loop–helix polypeptides are utilized tocontrol the assembly of gold nanoparticles and as scaffolds for biosensing. The synthetic polypeptides aredesigned to fold into a four-helix bundle upon dimerization. When immobilized on gold nanoparticles,dimerization and folding occur between peptides on neighbouring particles as an effect of particleaggregation and the folded polypeptides are rigid enough to keep the particles separated at a distancecorresponding to the size of the four-helix bundle. Moreover, peptide dimerization offers a convenientroute to assemble nanoparticles into hybrid multilayers on planar substrates. The drastic change in theresonance conditions of the localized nanoparticle surface plasmon upon particle aggregation is shown tobe useful for optical detection of biomolecular interactions.

  • 2.
    Eilers, Gerriet
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Molecular Approaches to Photochemical Solar Energy Conversion: Towards Synthetic Catalysts for Water Oxidation and Proton Reduction2007Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    A molecular system capable of photoinduced water splitting is an attractive approach to solar energy conversion. This thesis deals with the functional characterization of molecular building blocks for the three principal functions of such a molecular system: Photoinduced accumulative charge separation, catalytic water oxidation, and catalytic proton reduction.

    Systems combining a ruthenium-trisbipyridine photosensitizer with multi-electron donors in form of dinuclear ruthenium or manganese complexes were investigated in view of the rate constants of electron transfer and excited state quenching. The kinetics were studied in the different oxidation states of the donor unit by combination of electrochemistry and time resolved spectroscopy. The rapid excited state quenching by the multi-electron donors points to the importance of redox intermediates for efficient accumulative photooxidation of the terminal donor.

    The redox behavior of manganese complexes as mimics of the water oxidizing catalyst in the natural photosynthetic reaction center was studied by electrochemical and spectroscopic methods. For a dinuclear manganese complex ligand exchange reactions were studied in view of their importance for the accumulative oxidation of the complex and its reactivity towards water. With the binding of substrate water, multiple oxidation in a narrow potential range and concomitant deprotonation of the bound water it was demonstrated that the manganese complex is capable of mimicking multiple aspects of photosynthetic water oxidation.

    A dinuclear iron complex was investigated as biomimetic proton reduction catalyst. The complex structurally mimics the active site of the iron-only hydrogenase enzyme and was designed to hold a proton on the bridging ligand and a hydride on the iron centers. Thermodynamics and kinetics of the protonation reactions and the electrochemical behavior of the different protonation states were studied in view of their potential catalytic performance.

    List of papers
    1. Iron hydrogenase active site mimic holding a proton and a hydride
    Open this publication in new window or tab >>Iron hydrogenase active site mimic holding a proton and a hydride
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    2006 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, no 5, p. 520-522Article in journal (Refereed) Published
    National Category
    Natural Sciences
    Identifiers
    urn:nbn:se:uu:diva-95871 (URN)
    Available from: 2007-05-04 Created: 2007-05-04 Last updated: 2017-12-14
    2. Ligand versus metal protonation of an iron hydrogenase active site mimic
    Open this publication in new window or tab >>Ligand versus metal protonation of an iron hydrogenase active site mimic
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    2007 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 13, no 25, p. 7075-7084Article in journal (Refereed) Published
    Abstract [en]

    The protonation behavior of the iron hydrogenase active-site mimic [Fe2(u-adt)(CO)4(PMe3)2] (1; adt=N-benzyl-azadithiolate) has been investigated by spectroscopic, electrochemical, and computational methods. The combination of an adt bridge and electron-donating phosphine ligands allows protonation of either the adt nitrogen to give [Fe2(μ-Hadt)(CO)4(PMe3)2]+ ([1H]+), the Fe-Fe bond to give [Fe2-(μ-adt)(μ-H)(CO)4(PMe3)2]+ ([1Hy]+), or both sites simultaneously to give [Fe2(μ-Hadt)(μ-H)(CO)4(PMe3)2]2+ ([1HHy]2+). Complex 1 and its protonation products have been characterized in acetonitrile solution by IR, 1H, and 31PNMR spectroscopy. The solution structures of all protonation states feature a basal/basal orientation of the phosphine ligands, which contrasts with the basal/apical structure of 1 in the solid state. Density functional calculations have been performed on all protonation states and a comparison between calculated and experimental spectra confirms the structural assignments. The ligand protonated complex [1H]+ (pKa =12) is the initial, metastable protonation product while the hydride [1Hy]+ (pKa=15) is the thermodynamically stable singly protonated form. Tautomerization of cation [1H]+ to [1Hy]+ does not occur spontaneously. However, it can be catalyzed by HCl (k=2.2M-1s-1), which results in the selective formation of cation [1Hy]+. The protonations of the two basic sites have strong mutual effects on their basicities such that the hydride (pKa=8) and the ammonium proton (pKa=5) of the doubly protonated cationic complex [1HHy]2+ are considerably more acidic than in the singly protonated analogues. The formation of dication [1HHy]2+ from cation [1H]+ is exceptionally slow with perchloric or trifluoromethanesulfonic acid (k= 0.15 M-1s-1), while the dication is formed substantially faster (k > 102 M-1 s-1) with hydrobromic acid. Electrochemically, 1 undergoes irreversible reduction at -2.2V versus ferrocene, and this potential shifts to -1.6, - 1.1, and -1.0 V for the cationic complexes [1H]+, [1Hy]+, and [1HHy]2+, respectively, upon protonation. The doubly protonated form [1HHy]2+ is reduced at less negative potential than all previously reported hydrogenase models, although catalytic proton reduction at this potential is characterized by slow turnover.

    Keywords
    density functional calculations, electrochemistry, enzyme models, hydride ligands, tautomerism
    National Category
    Chemical Sciences
    Identifiers
    urn:nbn:se:uu:diva-95872 (URN)10.1002/chem.200700019 (DOI)000249294300005 ()17566128 (PubMedID)
    Available from: 2007-05-04 Created: 2007-05-04 Last updated: 2017-12-14Bibliographically approved
    3. Synthesis and characterization of dinuclear ruthenium complexes covalently linked to Ru(II) tris-bipyridine: an approach to mimics of the donor side of photosystem II
    Open this publication in new window or tab >>Synthesis and characterization of dinuclear ruthenium complexes covalently linked to Ru(II) tris-bipyridine: an approach to mimics of the donor side of photosystem II
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    2005 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 11, no 24, p. 7305-7314Article in journal (Refereed) Published
    Abstract [en]

    The structural rearrangements triggered by oxidation of the dinuclear Mn complex [Mn2(bpmp)(u-OAc)2]+ (bpmp = 2,6-bis[bis(2-pyridylmethyl)amino]methyl-4-methylphenol anion) in the presence of water have been studied by combinations of electrochemistry with IR spectroscopy and with electrospray ionization mass spectrometry (ESI-MS). The exchange of acetate bridges for water (D2O) derived ligands in different oxidation states could be monitored by mid-IR spectroscopy in CD3CN-D2O mixtures following the Vas(C-O) bands of bound acetate at 1594.4 cm-1 (II,II), 1592.0 cm-1 (II,III) and 1586.5 cm-1 (III,III). Substantial loss of bound acetate occurs at much lower water content (<0.5% v/v) in the III,III state than in the II,II and II,III states (>10%). The ligand-exchange reactions do not initially reduce the overall charge of the complex but facilitate further oxidation by proton-coupled electron transfer as the water-derived ligands are increasingly deprotonated in higher oxidation states. In the IR spectra deprotonation could be followed by the formation of acetic acid (DOAc, ~1725 cm-1, V(C-O)) from the released acetate (1573.6 cm-1, Vas(C-O)). By the on-line combination of an electrochemical flow cell with ESI-MS several product complexes could be identified. A di-u-oxo bridged III,IV dimer [Mn2(bpmp)(u-O)2]2+ (m/z 335.8) can be generated at potentials below the III,III/II,III couple of the di-u-acetato complex (0.61 V Vs. ferrocene). The ligand-exchange reactions allow for three metal-centered oxidation steps to occur from II,II to III,IV in a potential range of only 0.5 V, explaining the formation of a spin-coupled III,IV dimer by photo-oxidation with [Ru(bpy)3]3+ in previous EPR studies.

    Keywords
    electrochemistry, electron transfer, mixed-valent compounds, ruthenium cluster, sensitizers
    National Category
    Natural Sciences
    Identifiers
    urn:nbn:se:uu:diva-95873 (URN)10.1002/chem.200500592 (DOI)16163754 (PubMedID)
    Available from: 2007-05-04 Created: 2007-05-04 Last updated: 2017-12-14
    4. Ligand exchange upon oxidation of a dinuclear Mn complex - Detection of structural changes by FT-IR spectroscopy and ESI-MS.
    Open this publication in new window or tab >>Ligand exchange upon oxidation of a dinuclear Mn complex - Detection of structural changes by FT-IR spectroscopy and ESI-MS.
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    2005 (English)In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, no 6, p. 1033-1041Article in journal (Refereed) Published
    National Category
    Natural Sciences
    Identifiers
    urn:nbn:se:uu:diva-95874 (URN)
    Available from: 2007-05-04 Created: 2007-05-04 Last updated: 2017-12-14
    5. Synthesis and redox properties of a [meso-tris(4-nitrophenyl) corrolato]Mn(III) complex.
    Open this publication in new window or tab >>Synthesis and redox properties of a [meso-tris(4-nitrophenyl) corrolato]Mn(III) complex.
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    2005 (English)In: Journal of Porphyrins and Phthalocyanines, ISSN 1088-4246, E-ISSN 1099-1409, no 9(6), p. 379-386Article in journal (Refereed) Published
    National Category
    Natural Sciences
    Identifiers
    urn:nbn:se:uu:diva-95875 (URN)
    Available from: 2007-05-04 Created: 2007-05-04 Last updated: 2017-12-14
  • 3. Hashemi, Payman
    et al.
    Zarjani, Razieh Afzari
    Abolghasemi, Mir Mehdi
    Olin, Åke
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Agarose film coated glass slides for preparation of pH optical sensors2007In: Sensors and actuators. B, Chemical, ISSN 0925-4005, E-ISSN 1873-3077, Vol. 121, no 2, p. 396-400Article in journal (Refereed)
    Abstract [en]

    A method for preparation of optical sensors was developed by agarose film coating on aminosilanated glass slides. An optical pH sensor was accordingly prepared by epoxy activation of the agarose film, followed by chemical immobilization of Neutral Red dye. In an optimized coupling pH of 12 and a dye concentration of 10(-2) mol L-1 a pH sensor for a pH range of 2-8.5 was obtained. A theoretical equation was derived using the extended Henderson-Hasselbalch equation that reproduced the measured data well. The sensor was mounted in a flow cell and successfully applied for on-line pH measurements. The sensor responded rapidly to the pH changes with a response time of less than 2 min and reproducibility better than 0.40% (R.S.D.). In comparison to a stand-alone agarose membrane, the agarose coated glass slide showed better physical properties and easier handling and application but slightly slower response times. No evidence of leaching of the dye or any signal drift was observed.

  • 4.
    Persson, Mikael
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Sivaev, Igor
    Winberg, Karl-Johan
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Gedda, Lars
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Malmström, Per-Uno
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Surgical Sciences, Urology.
    Tolmachev, Vladimir
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology.
    In vitro evaluation of two polyhedral boron anion derivatives as linkers for attachment of radioiodine to the anti-HER2 monoclonal antibody trastuzumab2007In: Cancer Biotherapy and Radiopharmaceuticals, ISSN 1084-9785, E-ISSN 1557-8852, Vol. 22, no 5, p. 585-596Article in journal (Refereed)
    Abstract [en]

    Improving intracellular retention is important for the use of radiohalogens in radionuclide therapy usinginternalizing antibodies. Two putative linkers for residualization of radioiodine labels, 7-(4-isothiocyanato-phenyl)undecahydro-7,8-dicarba-nido-undecaborate(1Ϫ) ion (NBI) and (4-isothiocyanato-benzylammo-nio)undecahydro-closo-dodecaborate(1Ϫ) (DABI), were analyzed. The anti-HER-2 antibody, trastuzumab,was labeled with iodine-125 using NBI and DABI linkers, and, for comparison, with the para-[125I]iodoben-zoate (PIB), and Chloramine-T (CAT) methods. The different labels were tested for residualizing prop-erties using the HER-2 overexpressing SKBR-3 cells. The cellular radioactivity retention showed thatDABI provided a 55% better retention than CAT and was 42% better than PIB after 20 hours. NBI didnot improve retention. Accumulation tests up to 21 hours showed that the HER-2-specific accumulationof radioactivity delivered with DABI was, on average, 33% higher than with the use of PIB. These DABI-dependent improvements could, with high probability, be attributed to the good residualizing propertiesof DABI. The affinity of DABI-labeled trastuzumab to SKBR-3 cells was not better than the affinity of thePIB labeled (3.2 Ϯ 1.9 nM and 0.77 Ϯ 0.39 nM, respectively). In conclusion, the use of the DABI linkerimproved intracellular retention in vitro in comparison with the other labeling methods.

  • 5.
    Polavarapu, Anjaneya Prasad
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Exploring Molecular Interactions: Synthesis and Studies of Clip-Shaped Molecular Hosts2007Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Molecular recognition via noncovalent interactions plays a key role in many biological processes such as antigen-antibody interactions, protein folding, the bonding and catalytic transformation of substrates by enzymes, etc. Amongst these noncovalent interactions, electrostatic interactions, hydrogen bonding, π-π interactions, and metal-to-ligand bonding are the most prominent. Exploring noncovalent interactions in host-guest systems that range from small hydrocarbon systems to more complex systems is the main motivation of this thesis. The present study involves the design, synthesis and characterization of clip-shaped molecules as host structures, and an examination of their binding properties with a variety of guests using NMR spectroscopy.

    Several clips with a hydrocarbon or glycoluril backbone were synthesized. The binding of cations to small, hydrocarbon-based clips suggests that binding is enhanced by the rigidity and cooperativity between the two sidewalls of the clip. Binding is also very much dependant on the solvent properties.

    Glycoluril-based clips built with aromatic sidewalls provide a deep cavity for binding guest molecules. The binding properties of these hosts were studied with several guests such as cations, Lewis acids and Lewis bases. Lewis basic binding sites in the acenaphthene-terminated clip were dominating in guest binding. Complexation-induced conformational changes in the wall-to-wall distance were observed for this clip.

    In contrast, for a porphyrin-terminated clip with metal centers, very strong binding to a series of Lewis basic guests of various sizes into the clip cavity was observed. Conformational locking of guests with long alkyl chains was achieved, suggesting that, this clip could be useful as a potential molecular tool for the structural characterization of acyclic molecules with several stereogenic centers. This porphyrin clip was also shown to bind substituted fullerenes in the cavity.

    List of papers
    1. Enhanced Silver Ion Binding to a Rigid Bisarene Molecular Cleft with Formation of Nonpolar Pleated Sheets through Non-Ionic Intermolecular Forces
    Open this publication in new window or tab >>Enhanced Silver Ion Binding to a Rigid Bisarene Molecular Cleft with Formation of Nonpolar Pleated Sheets through Non-Ionic Intermolecular Forces
    2007 (English)In: Inorganic Chemistry, ISSN 0020-1669, E-ISSN 1520-510X, Vol. 46, no 13, p. 5271-5275Article in journal (Refereed) Published
    Abstract [en]

    Silver ion complexation to bisarene ligands is enhanced by providing a conformationally rigid molecular cleft in the (Z)-acenaphthylene dimer 1. NMR titrations were used to determine complexation constants K for a series of ligands in tetrahydrofuran solution, with K = 4.9 M-1 for the Z dimer 1 and 0.4 M-1 for the E dimer 2. Higher values of K were observed in CDCl3/CD3OD 9:1 with K = 38 M-1 for 1 and K = 4.1 M-1 for 2. In the solid state, isolated clusters of [1·(AgCF3SO3)2]2 form a novel, pleated-sheet motif based on non-ionic interactions between clusters.

    National Category
    Chemical Sciences
    Identifiers
    urn:nbn:se:uu:diva-96237 (URN)10.1021/ic070222z (DOI)000247304600024 ()
    Available from: 2007-09-26 Created: 2007-09-26 Last updated: 2017-12-14Bibliographically approved
    2. Modulation and binding properties of extended glycoluril molecular clips
    Open this publication in new window or tab >>Modulation and binding properties of extended glycoluril molecular clips
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    2008 (English)In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 32, no 4, p. 643-651Article in journal (Refereed) Published
    Abstract [en]

    A glycoluril clip (1) provides a deep cavity for binding of guest molecules. Guest species interact preferentially via hydrogen bonding or ion - lone pair interactions. Complexation-induced conformational modulation of the cavity wall distance was observed. At higher guest - host ratios, inclusion compounds with organic guest molecules are obtained. The X-ray crystallographic structure of 1 center dot(NH4PF6) center dot 3CHCl(3) center dot 2CH(3)OH shows formation of a network of clips connected via polar and non-polar interactions.

    National Category
    Chemical Sciences
    Identifiers
    urn:nbn:se:uu:diva-96238 (URN)10.1039/b715208f (DOI)000254634300008 ()
    Available from: 2007-09-26 Created: 2007-09-26 Last updated: 2017-12-14Bibliographically approved
    3. A Porphyrin Terminated Molecular Tweezer for Conformational Restriction of Flexible Molecules in Solution.
    Open this publication in new window or tab >>A Porphyrin Terminated Molecular Tweezer for Conformational Restriction of Flexible Molecules in Solution.
    Article in journal (Refereed) Submitted
    Identifiers
    urn:nbn:se:uu:diva-96239 (URN)
    Available from: 2007-09-26 Created: 2007-09-26Bibliographically approved
    4. Buckyball in the Clip: A Molecular Tweezer That Binds Fullerenes.
    Open this publication in new window or tab >>Buckyball in the Clip: A Molecular Tweezer That Binds Fullerenes.
    Manuscript (Other academic)
    Identifiers
    urn:nbn:se:uu:diva-96240 (URN)
    Available from: 2007-09-26 Created: 2007-09-26 Last updated: 2010-01-13Bibliographically approved
  • 6.
    Sunnerheim, Kerstin
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Nordqvist, Anneli
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Nordlander, Göran
    Borg-Karlson, Anna-Karin
    Unelius, Rickard
    Bohman, Björn
    Nordenhem, Henrik
    Hellqvist, Claes
    Karlén, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Quantitative structure-activity relationships of pine weevil antifeedants, a multivariate approach2007In: Journal of Agricultural and Food Chemistry, ISSN 0021-8561, E-ISSN 1520-5118, Vol. 55, no 23, p. 9365-9372Article in journal (Refereed)
    Abstract [en]

    Antifeedant activity of mainly phenylpropanoic, cinnamic, and benzoic acids esters was tested on the pine weevil, Hylobius abietis (L.). Of 105 compounds screened for activity, 9 phenylpropanoates, 3 cinnamates, and 4 benzoates were found to be highly active antifeedants. To understand the structure–activity relationships of these compounds, a multivariate analysis study was performed. A number of molecular and substituent descriptors were calculated and correlated to results from two-choice feeding tests with H. abietis. Three local models were developed that had good internal predictive ability. External test sets showed moderate predictivity. In general, low polarity, small size, and high lipophilicity were characteristics for compounds having good antifeedant activity.

  • 7. Wållberg, Maja
    et al.
    Bergquist, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Analytical Chemistry.
    Achour, Adnane
    Breij, Esther
    Harris, Robert A.
    Malondialdehyde modification of myelin oligodendrocyte glycoprotein leads to increased immunogenicity and encephalitogenicity2007In: European Journal of Immunology, ISSN 0014-2980, E-ISSN 1521-4141, Vol. 37, no 7, p. 1986-1995Article in journal (Refereed)
    Abstract [en]

    Self proteins may become autoantigenic through structural modification. We studied malondialdehydation of recombinant rat (rr) myelin oligodendrocyte glycoprotein (MOG), an autoantigen in multiple sclerosis. Malondialdehyde (MDA) modification changed protein weight and charge, the location of these adducts being mapped by Fourier transform ion cyclotron resonance. Molecular modelling revealed significant differences in the MDA-rrMOG three-dimensional structure. DBA/1 mice immunised with MDA-rrMOG developed greater proliferative responses and more severe experimental autoimmune encephalomyelitis than mice immunised with unmodified rrMOG. MDA-rrMOG was taken up more effectively by antigen-presenting cells (APC), at least partially through scavenger receptors. Exposure to MDA-rrMOG led to increased expression of IL-23, IL-12 and IL-12R, indicating a role not only for increased antigen uptake but also for activation of APC. We thus provide biochemical, structural, immunological and clinical data that suggest that the post-translationally modified form of this myelin autoantigen is a more relevant form of the molecule.

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