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C2-symmetric inhibitors of Plasmodium falciparum plasmepsin II: synthesis and theoretical predictions
Uppsala University.
Uppsala University.
Uppsala University.ORCID iD: 0000-0002-9300-614X
Uppsala University.
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2003 (English)In: Bioorganic & Medicinal Chemistry, ISSN 0968-0896, E-ISSN 1464-3391, Vol. 11, no 17, 3723-3733 p.Article in journal (Refereed) Published
Abstract [en]

A series of C(2)-symmetric compounds with a mannitol-based scaffold has been investigated, both theoretically and experimentally, as Plm II inhibitors. Four different stereoisomers with either benzyloxy or allyloxy P1/P1' side chains were studied. Computational ranking of the binding affinities of the eight compounds was carried out using the linear interaction energy (LIE) method relying on a complex previously determined by crystallography. Within both series of isomers the theoretical binding energies were in agreement with the enzymatic measurements, illustrating the power of the LIE method for the prediction of ligand affinities prior to synthesis. The structural models of the enzyme-inhibitor complexes obtained from the MD simulations provided a basis for interpretation of further structure-activity relationships. Hence, the affinity of a structurally similar ligand, but with a different P2/P2' substituent was examined using the same procedure. The predicted improvement in binding constant agreed well with experimental results.

Place, publisher, year, edition, pages
2003. Vol. 11, no 17, 3723-3733 p.
National Category
Biochemistry and Molecular Biology
Research subject
Chemistry, Biochemistry
Identifiers
URN: urn:nbn:se:lnu:diva-51106DOI: 10.1016/S0968-0896(03)00339-0PubMedID: 12901917OAI: oai:DiVA.org:lnu-51106DiVA: diva2:913261
Available from: 2016-03-21 Created: 2016-03-21 Last updated: 2016-05-02Bibliographically approved

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