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Publications (10 of 151) Show all publications
Umereweneza, D., Atilaw, Y., Peintner, S., Rudenko, A., Bourgard, C., Xiong, R., . . . Erdélyi, M. (2023). Macrocyclic Pyrrolizidine Alkaloids and Silphiperfolanol Angelate Esters from Solanecio mannii. European Journal of Organic Chemistry, 26(8), Article ID e202201280.
Open this publication in new window or tab >>Macrocyclic Pyrrolizidine Alkaloids and Silphiperfolanol Angelate Esters from Solanecio mannii
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2023 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 26, no 8, article id e202201280Article in journal (Refereed) Published
Abstract [en]

Three new compounds, the silphiperfolanol angelate ester umutagarananol (1), the macrocyclic pyrrolizidine alkaloids umutagarinine A and B (23), and five known secondary metabolites (48) were isolated from the CH2Cl2−MeOH (1 : 1) extract of the roots and the stem bark of Solanecio mannii (Hook. f.) (Asteraceae). The isolated compounds were characterized by NMR and IR spectroscopic, and mass spectrometric analyses, whereas the relative stereochemistry of 4 was established by NAMFIS-based combined computational and solution NMR analysis. Synthetic modification of 5 provided two new compounds, 2-angeloyloxy-4,8-epoxypresilphiperfolane (9) and 2-angeloyloxy-4,8-epoxypresilphi-perfolane (10). The crude extracts and the isolated constituents showed weak antibacterial activities (EC50 0.7–13.3 mM) against the Gram-negative Escherichia coli and the Gram-positive Bacillus subtilis. Compounds 2, 3 and 4 exhibited strong cytotoxicity against MCF-7 human breast cancer cells, with EC50 values of 35.6, 21.7 and 12.5 μM, respectively.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2023
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-507379 (URN)10.1002/ejoc.202201280 (DOI)000921628000001 ()
Funder
Swedish Research Council, 2019-03715Uppsala University, RWA-01
Available from: 2023-07-05 Created: 2023-07-05 Last updated: 2023-07-05Bibliographically approved
Naranjani, B., Sinko, P. D., Bergström, C., Gogoll, A., Hossain, M. S. & Larsson, P. (2023). Numerical simulation of peristalsis to study co-localization and intestinal distribution of a macromolecular drug and permeation enhancer. International Journal of Biological Macromolecules, 240, Article ID 124388.
Open this publication in new window or tab >>Numerical simulation of peristalsis to study co-localization and intestinal distribution of a macromolecular drug and permeation enhancer
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2023 (English)In: International Journal of Biological Macromolecules, ISSN 0141-8130, E-ISSN 1879-0003, Vol. 240, article id 124388Article in journal (Refereed) Published
Abstract [en]

In this work, simulations of intestinal peristalsis are performed to investigate the intraluminal transport of macromolecules (MMs) and permeation enhancers (PEs). Properties of insulin and sodium caprate (C10) are used to represent the general class of MM and PE molecules. Nuclear magnetic resonance spectroscopy was used to obtain the diffusivity of C10, and coarse-grain molecular dynamics simulations were carried out to estimate the concentration-dependent diffusivity of C10. A segment of the small intestine with the length of 29.75 cm was modeled. Peristaltic speed, pocket size, release location, and occlusion ratio of the peristaltic wave were varied to study the effect on drug transport. It was observed that the maximum concentration at the epithelial surface for the PE and the MM increased by 397 % and 380 %, respectively, when the peristaltic wave speed was decreased from 1.5 to 0.5 cm s−1. At this wave speed, physiologically relevant concentrations of PE were found at the epithelial surface. However, when the occlusion ratio is increased from 0.3 to 0.7, the concentration approaches zero. These results suggest that a slower-moving and more contracted peristaltic wave leads to higher efficiency in transporting mass to the epithelial wall during the peristalsis phases of the migrating motor complex.

Place, publisher, year, edition, pages
Elsevier, 2023
Keywords
Oral delivery, Permeation enhancement, Molecular diffusivity, Computational modeling, Peristaltic motility, Bioavailability
National Category
Pharmaceutical Sciences
Identifiers
urn:nbn:se:uu:diva-502000 (URN)10.1016/j.ijbiomac.2023.124388 (DOI)000990704100001 ()37059282 (PubMedID)
Funder
Vinnova, 2019-00048
Available from: 2023-05-19 Created: 2023-05-19 Last updated: 2023-06-20Bibliographically approved
Umereweneza, D., Atilaw, Y., Rudenko, A., Gütlin, Y., Bourgard, C., Gupta, A. K., . . . Gogoll, A. (2021). Antibacterial and cytotoxic prenylated dihydrochalcones from Eriosema montanum. Fitoterapia (Milano), 149, Article ID 104809.
Open this publication in new window or tab >>Antibacterial and cytotoxic prenylated dihydrochalcones from Eriosema montanum
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2021 (English)In: Fitoterapia (Milano), ISSN 0367-326X, E-ISSN 1873-6971, Vol. 149, article id 104809Article in journal (Refereed) Published
Abstract [en]

Two new prenylated dihydrochalcones (1,2) and eighteen known secondary metabolites (320) were isolated from the CH2Cl2-MeOH (1:1) extracts of the roots, the stem bark and the leaves of Eriosema montanum Baker f. (Leguminosae). The structures of the isolated compounds were characterized by NMR, IR, and UV spectroscopic and mass spectrometric analyses. The structures of compounds 5, 10, 11 and 13 were confirmed by single crystal X-ray diffraction. The antibacterial activity of the crude extracts and the isolated constituents were established against Gram-positive and Gram-negative bacteria. Among the tested compounds, 14 and 10 showed strong activity against the Gram-positive bacterium Bacillus subtilis with minimum inhibitory concentration (MIC) ranging from 3.1 to 8.9 μM, as did the leaf crude extract with an MIC of 3.0 μg/mL. None of the crude extracts nor the isolated compounds were active against Escherichia coli. Compounds 1, 3 and 4 showed higher cytotoxicity, evaluated against the human breast cancer cell line MCF-7, with EC50 of 7.0, 18.0 and 18.0 μM, respectively. These findings contribute to the phytochemical understanding of the genus Eriosema, and highlight the pharmaceutical potential of prenylated dihydrochalcones.

Keywords
Eriosema montanum, Leguminosae, Dihydrochalcone, Cytotoxicity, Antibacterial activity, Flavonoids
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-432887 (URN)10.1016/j.fitote.2020.104809 (DOI)000619206900006 ()33359421 (PubMedID)
Funder
Swedish Research Council, 2019-03715
Available from: 2021-01-23 Created: 2021-01-23 Last updated: 2022-04-20Bibliographically approved
Umereweneza, D., Molel, J. T., Said, J., Atilaw, Y., Muhizi, T., Trybala, E., . . . Erdélyi, M. (2021). Antiviral iridoid glycosides from Clerodendrum myricoides. Fitoterapia, 155, Article ID 105055.
Open this publication in new window or tab >>Antiviral iridoid glycosides from Clerodendrum myricoides
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2021 (English)In: Fitoterapia, ISSN 0367-326X, E-ISSN 1873-6971, Vol. 155, article id 105055Article in journal (Refereed) Published
Abstract [en]

The methanol root extract of Clerodendrum myricoides (Hochst.) Vatke afforded two new (1, 2) and two known (3, 4) iridoid glycosides. The structures of the isolated compounds were established based on NMR, IR, UV and MS data analyses. The crude extract and the isolated constituents were assayed for antiviral activity against the human respiratory syncytial virus (RSV) in human laryngeal epidermoid carcinoma (HEp-2) cells. The crude extract inhibited RSV infectivity at EC50 = 0.21 μg/ml, while it showed cytotoxicity against HEp-2 cells with CC50 = 9 μg/ml. Compound 2 showed 43.2% virus inhibition at 100 μM, while compounds 1 as well as 3 and 4 had only weak antiviral and cytotoxic activities.

Place, publisher, year, edition, pages
ElsevierElsevier BV, 2021
Keywords
Clerodendrum myricoides, Lamiaceae, Iridoid glycosides, RSV inhibitor, Antiviral activity
National Category
Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-457969 (URN)10.1016/j.fitote.2021.105055 (DOI)000710100600006 ()34626739 (PubMedID)
Funder
Swedish Research Council
Available from: 2021-11-04 Created: 2021-11-04 Last updated: 2024-01-15Bibliographically approved
Huang, H., Strömme, M., Gogoll, A. & Sjödin, M. (2021). Potential-tuning in quinone-pyrrole dyad-based conducting redox polymers. Electrochimica Acta, 389, 19099-19108
Open this publication in new window or tab >>Potential-tuning in quinone-pyrrole dyad-based conducting redox polymers
2021 (English)In: Electrochimica Acta, ISSN 0013-4686, E-ISSN 1873-3859, Vol. 389, p. 19099-19108Article in journal (Refereed) Published
Abstract [en]

In this study, conducting redox polymers (CRPs), which consist of a polypyrrole conducting polymer backbone with attached quinone pendant groups, have been explored as electrode materials for organic batteries. A modular organic synthetic approach is presented that allows the assembly of pyrrole and quinone units into quinone-pyrrole dyads and modifying the dyads by varying the substitution pattern on the quinone moiety. These dyad monomers were copolymerized electrochemically with pyrrole to yield the CRPs with quinone formal potentials varying within a 0.6 V range. With access to CRP materials with tunable quinone formal potentials an all-organic water-based battery was constructed by choosing CRPs with different quinone potentials as anode and cathode material. Galvanostatic charge-discharge of the cell showed that the cell potentials coincided well with the difference in redox potential between the quinone substituents used in the anode and cathode CRP.

Place, publisher, year, edition, pages
Elsevier, 2021
Keywords
Conducting redox polymer, Organic batteries, Quinone electrochemistry
National Category
Materials Chemistry
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
urn:nbn:se:uu:diva-449424 (URN)10.1016/j.electacta.2021.138758 (DOI)000687334700011 ()
Available from: 2021-07-26 Created: 2021-07-26 Last updated: 2024-01-15Bibliographically approved
Guo, X., Söderholm, A., Kanchugal Puttaswamy, S., Isaksen, G. V., Warsi, O. M., Eckhard, U., . . . Selmer, M. (2021). Structure and mechanism of a phage-encoded SAM lyase revises catalytic function of enzyme family. eLIFE, 10, Article ID e61818.
Open this publication in new window or tab >>Structure and mechanism of a phage-encoded SAM lyase revises catalytic function of enzyme family
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2021 (English)In: eLIFE, E-ISSN 2050-084X, Vol. 10, article id e61818Article in journal (Refereed) Published
Abstract [en]

The first S-adenosyl methionine (SAM) degrading enzyme (SAMase) was discovered in bacteriophage T3, as a counter-defense against the bacterial restriction-modification system, and annotated as a SAM hydrolase forming 5’-methyl-thioadenosine (MTA) and L-homoserine. From environmental phages, we recently discovered three SAMases with barely detectable sequence similarity to T3 SAMase and without homology to proteins of known structure. Here, we present the very first phage SAMase structures, in complex with a substrate analogue and the product MTA. The structure shows a trimer of alpha–beta sandwiches similar to the GlnB-like superfamily, with active sites formed at the trimer interfaces. Quantum-mechanical calculations, thin-layer chromatography, and nuclear magnetic resonance spectroscopy demonstrate that this family of enzymes are not hydrolases but lyases forming MTA and L-homoserine lactone in a unimolecular reaction mechanism. Sequence analysis and in vitro and in vivo mutagenesis support that T3 SAMase belongs to the same structural family and utilizes the same reaction mechanism.

Place, publisher, year, edition, pages
eLife Sciences Publications Ltd, 2021
National Category
Structural Biology Biochemistry and Molecular Biology
Research subject
Biology with specialization in Structural Biology
Identifiers
urn:nbn:se:uu:diva-437495 (URN)10.7554/eLife.61818 (DOI)000619641100001 ()33567250 (PubMedID)
Funder
Swedish Research Council, 2017–03827Knut and Alice Wallenberg Foundation, Evolution of new genes and proteinsSwedish Research Council, 2017-01527
Available from: 2021-03-10 Created: 2021-03-10 Last updated: 2024-01-15Bibliographically approved
Alvebratt, C., Dening, T. J., Åhlén, M., Cheung, O., Strömme, M., Gogoll, A., . . . Bergström, C. A. S. (2020). In Vitro Performance and Chemical Stability of Lipid-Based Formulations Encapsulated in a Mesoporous Magnesium Carbonate Carrier. Pharmaceutics, 12(5), Article ID 426.
Open this publication in new window or tab >>In Vitro Performance and Chemical Stability of Lipid-Based Formulations Encapsulated in a Mesoporous Magnesium Carbonate Carrier
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2020 (English)In: Pharmaceutics, ISSN 1999-4923, E-ISSN 1999-4923, Vol. 12, no 5, article id 426Article in journal (Refereed) Published
Abstract [en]

Lipid-based formulations can circumvent the low aqueous solubility of problematic drug compounds and increase their oral absorption. As these formulations are often physically unstable and costly to manufacture, solidification has been suggested as a way to minimize these issues. This study evaluated the physicochemical stability and in vitro performance of lipid-loaded mesoporous magnesium carbonate (MMC) particles with an average pore size of 20 nm. A medium chain lipid was loaded onto the MMC carrier via physical adsorption. A modified in vitro lipolysis setup was then used to study lipid release and digestion with 1H nuclear magnetic resonance spectroscopy. The lipid loading efficiency with different solidification techniques was also evaluated. The MMC, unlike more commonly used porous silicate carriers, dissolved during the lipolysis assay, providing a rapid release of encapsulated lipids into solution. The digestion of the dispersed lipid-loaded MMC therefore resembled that of a coarse dispersion of the lipid. The stability data demonstrated minor degradation of the lipid within the pores of the MMC particles, but storage for three months did not reveal extensive degradation. To conclude, lipids can be adsorbed onto MMC, creating a solid powder from which the lipid is readily released into the solution during in vitro digestion. The chemical stability of the formulation does however merit further attention.

Keywords
1H nuclear magnetic resonance, lipid release, lipid-based formulations, lipolysis, mesoporous magnesium carbonate, solidification
National Category
Nano Technology Pharmaceutical Sciences
Research subject
Engineering Science with specialization in Nanotechnology and Functional Materials
Identifiers
urn:nbn:se:uu:diva-414278 (URN)10.3390/pharmaceutics12050426 (DOI)000543393700038 ()32384752 (PubMedID)
Funder
Swedish Research Council, 621-2014-3929
Available from: 2020-06-24 Created: 2020-06-24 Last updated: 2020-11-23Bibliographically approved
Olsson, S. K., Benito Perez, O., Blom, M. & Gogoll, A. (2019). Effect of Ring Size on Photoisomerization Properties of Stiff Stilbene macrocycles. Beilstein Journal of Organic Chemistry, 15, 2408-2418
Open this publication in new window or tab >>Effect of Ring Size on Photoisomerization Properties of Stiff Stilbene macrocycles
2019 (English)In: Beilstein Journal of Organic Chemistry, ISSN 2195-951X, E-ISSN 1860-5397, Vol. 15, p. 2408-2418Article in journal (Refereed) Published
Abstract [en]

A series of stiff stilbene macrocycles have been studied to investigate the possible impact of the macrocycle ring size on their photodynamic properties. The results show that reducing the ring size counteracts the photoisomerization ability of the macrocycles. However, even the smallest macrocycle studied (stiff stilbene subunits linked by a six carbon chain) showed some degree of isomerization when irradiated. DFT calculations of the energy differences between the E- and Z-isomers show the same trend as the experimental results. Interestingly the DFT study highlights that the energy difference between the E- and Z-isomers of even the largest macrocycle (linked by a twelve carbon chain) is significantly higher than that of the stiff stilbene unit itself. In general, it is indicated that addition of even a flexible chain to the stiff stilbene unit may significantly affect its photochemical properties and increase the photostability of the resulting macrocycle.

Keywords
Stiff stilbene cyclic photoisomerization
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-382215 (URN)10.3762/bjoc.15.233 (DOI)000489716300001 ()31666875 (PubMedID)
Funder
Swedish Research Council, 621-2012-3379Carl Tryggers foundation , CTS 16:156Swedish National Infrastructure for Computing (SNIC)
Available from: 2019-04-23 Created: 2019-04-23 Last updated: 2019-11-08Bibliographically approved
Norrehed, S., Karlsson, C., Light, M. E., Thapper, A., Huang, P. & Gogoll, A. (2019). Formation of persistent organic diradicals from N,N'-diphenyl-3,7- diazacyclooctanes. Monatshefte fuer Chemie, 150(1), 77-84
Open this publication in new window or tab >>Formation of persistent organic diradicals from N,N'-diphenyl-3,7- diazacyclooctanes
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2019 (English)In: Monatshefte fuer Chemie, ISSN 0026-9247, E-ISSN 1434-4475, Vol. 150, no 1, p. 77-84Article in journal (Refereed) Published
Abstract [en]

N,N'-Diphenyl-3,7-diazacyclooctane and structurally related N,N'-diphenylbispidine derivatives react with silver(I) ions in a high-yielding C–C coupling reaction to produce dication–diradical species, with the silver ions serving a double function both as template and as an oxidant. The resulting bis(benzidino)phane derivatives are persistent organic radicals, stable for several months in solution as well as in the solid state, at room temperature and above, as well as being exposed to the atmosphere. The molecular structure features a double-decker cyclophane motif, stabilized by intramolecular π-dimerization of two delocalized benzidinium radical segments. Intermolecular π-dimers are formed in the solid state.

Place, publisher, year, edition, pages
Vienna: Springer, 2019
Keywords
Biaryls, Crystal structure, Heterocycles, Oxidative coupling, biradicals
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-364531 (URN)10.1007/s00706-018-2298-4 (DOI)000454953600009 ()
Funder
Swedish Research Council
Available from: 2018-10-29 Created: 2018-10-29 Last updated: 2019-01-28Bibliographically approved
Olsson, S. K., Dahlstrand, C. & Gogoll, A. (2018). Design of oxophilic metalloporphyrins: an experimental and DFT study of methanol binding. Dalton Transactions, 47(33), 11572-11585
Open this publication in new window or tab >>Design of oxophilic metalloporphyrins: an experimental and DFT study of methanol binding
2018 (English)In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 47, no 33, p. 11572-11585Article in journal (Refereed) Published
Abstract [en]

By systematic measurements we have evaluated a series of tetraphenyl metalloporphyrins and halogenated tetraphenyl metalloporphyrin derivatives for binding to ligands with oxygen containing functional groups, using methanol, acetic acid and acetone as examples. Experimental binding constants identified three metalloporphyrins with good binding to all three ligands: MgTPFPP, MgTPPBr8 and ZnTPPBr8 as well as a range of porphyrins binding to select ligands. Based on these results the optimal porphyrins can be selected for the desired binding interactions. We also show how to use DFT calculations to evaluate the potential binding between a metalloporphyrin and a ligand, which is deduced from free energies of binding ΔG, charge transfer ΔQ, and change of metal spin state. Computations on unsubstituted porphyrins in lieu of tetraphenyl porphyrin systems yield reliable predictions of binding interactions with good correlation to the corresponding experimental data. The calculations have also yielded interesting insights into the effect of halogenation in the β-position on the binding to ligands with oxygen containing functional groups.

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2018
Keywords
Porphyrins, DFT, host-guest
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-359830 (URN)10.1039/c8dt02432d (DOI)000442509700031 ()30087966 (PubMedID)
Funder
Swedish Research Council, 621-2012-3379Carl Tryggers foundation , 16:156Swedish National Infrastructure for Computing (SNIC), 2018/3-240National Supercomputer Centre (NSC), Sweden, SNIC 2018/3-240
Available from: 2018-09-06 Created: 2018-09-06 Last updated: 2019-04-23Bibliographically approved
Projects
Modulation of molecular properties by external steering: Photoswitchable peptidomimetics and conformational restrictors [2009-04718_VR]; Uppsala UniversityModulated molecular functionality in peptidomimetics and supramolecular systems [2012-03379_VR]; Uppsala University
Organisations
Identifiers
ORCID iD: ORCID iD iconorcid.org/0000-0002-9092-261X

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