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Going Viral: An Investigation into the Chameleonic Behaviour of Antiviral Compounds
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.ORCID iD: 0000-0003-4617-7605
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.ORCID iD: 0000-0003-2899-9912
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.ORCID iD: 0000-0002-8880-9247
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Organic Chemistry.ORCID iD: 0000-0003-0359-5970
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2023 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 29, no 8, article id e202202798Article in journal (Refereed) Published
Abstract [en]

The ability to adjust conformations in response to the polarity of the environment, i.e. molecular chameleonicity, is considered to be important for conferring both high aqueous solubility and high cell permeability to drugs in chemical space beyond Lipinski's rule of 5. We determined the conformational ensembles populated by the antiviral drugs asunaprevir, simeprevir, atazanavir and daclatasvir in polar (DMSO-d6) and non-polar (chloroform) environments with NMR spectroscopy. Daclatasvir was fairly rigid, whereas the first three showed large flexibility in both environments, that translated into major differences in solvent accessible 3D polar surface area within each conformational ensemble. No significant differences in size and polar surface area were observed between the DMSO-d6 and chloroform ensembles of these three drugs. We propose that such flexible compounds are characterized as “partial molecular chameleons” and hypothesize that their ability to adopt conformations with low polar surface area contributes to their membrane permeability and oral absorption.

Place, publisher, year, edition, pages
Wiley-VCH Verlagsgesellschaft, 2023. Vol. 29, no 8, article id e202202798
Keywords [en]
antiviral drugs, conformation analysis, drug design, NMR spectroscopy, partial molecular chameleon
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-500064DOI: 10.1002/chem.202202798ISI: 000898258400001PubMedID: 36286339OAI: oai:DiVA.org:uu-500064DiVA, id: diva2:1749840
Funder
Uppsala UniversitySwedish National Infrastructure for Computing (SNIC)Swedish Research Council, 201805973Swedish Research Council, 2021/5-359Swedish Research Council, 2021/22-350Swedish Research Council, 2021-04747Swedish Research Council, 2020-03431Available from: 2023-04-11 Created: 2023-04-11 Last updated: 2023-07-05Bibliographically approved
In thesis
1. Bringing Structure to Drug Discovery
Open this publication in new window or tab >>Bringing Structure to Drug Discovery
2023 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Drug discovery is aided by structural information. The type of structural information needed depends on the question at hand. The methods that can be used to determine the absolute configuration of a newly synthesised compound are different from those needed to study ligand binding. This thesis employs a set of structural techniques to study a variety of research questions.

NMR methods were used to understand the binding of an inhibitor to an enzyme responsible for antibiotic resistance. This thesis describes the backbone resonance assignment of the enzyme and the investigation of the protein-ligand interaction. The binding-site as well as the binding-affinity were investigated.

Obtaining insights into the passive membrane permeability of unconventionally large drugs was achieved by looking at their solution ensembles in polar and apolar environments. NMR experiments were used to obtain the solution ensembles of eight antimicrobial and antiviral drugs.

One of the antiviral drugs was studied by MicroED, a new methodology capable of obtaining crystal structures. MicroED requires less material, smaller crystals and the crystals can be of lower quality as compared to conventional X-ray diffraction. This thesis shows that MicroED can be used to obtain the crystal structure of a flexible small molecule that is challenging to elucidate by X-ray crystallography.

The final study of this thesis investigated the applicability of time-saving sampling schemes for the acquisition of quantitative NOESY data. It explores different variables, but none of the investigated conditions lead to the level of accuracy needed for NOE-based distance determination.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2023. p. 69
Series
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 2262
National Category
Chemical Sciences
Identifiers
urn:nbn:se:uu:diva-500237 (URN)978-91-513-1794-6 (ISBN)
Public defence
2023-06-02, Room A1:111a, BMC, Husargatan 3, Uppsala, 09:15 (English)
Opponent
Supervisors
Available from: 2023-05-10 Created: 2023-04-13 Last updated: 2023-05-10

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Wieske, Lianne H. E.Atilaw, YosephPoongavanam, VasanthanathanErdélyi, MátéKihlberg, Jan

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