Natural product hybrid and its superacid synthesized analogues: Dodoneine and its derivatives show selective inhibition of carbonic anhydrase isoforms I, III, XIII and XIV'
| Autor: | Jérôme Marrot, Jean-Marie Coustard, Clarisse Vandebrouck, Jocelyn Bescond, Daniella Vullo, Maurice Ouedraogo, Grégoire Carré, Hélène Carreyre, Claudiu T. Supuran, Sébastien Thibaudeau |
|---|---|
| Přispěvatelé: | Synthèse Organique (E5), Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Poitiers-Institut de Chimie du CNRS (INC)-Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Poitiers-Institut de Chimie du CNRS (INC) |
| Jazyk: | angličtina |
| Rok vydání: | 2013 |
| Předmět: |
Gene isoform
Stereochemistry Clinical Biochemistry Pharmaceutical Science 010402 general chemistry 01 natural sciences Biochemistry Loranthaceae chemistry.chemical_compound Phenols Carbonic anhydrase Drug Discovery Humans Protein Isoforms Carbonic Anhydrase Inhibitors Molecular Biology ComputingMilieux_MISCELLANEOUS Carbonic Anhydrases chemistry.chemical_classification Natural product biology 010405 organic chemistry Plant Extracts [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry [CHIM.CATA]Chemical Sciences/Catalysis 0104 chemical sciences chemistry biology.protein Molecular Medicine Superacid Selectivity [CHIM.OTHE]Chemical Sciences/Other Lead compound Lactone |
| Zdroj: | Bioorganic and Medicinal Chemistry Bioorganic and Medicinal Chemistry, Elsevier, 2013, 21, pp.3790-3794. ⟨10.1016/j.bmc.2013.04.041⟩ Bioorganic & Medicinal Chemistry; Vol 21 Bioorganic & Medicinal Chemistry |
| ISSN: | 0968-0896 1464-3391 |
| Popis: | The natural product dodoneine (a dihydropyranone phenolic compound), extracted from African mistletoe Agelanthus dodoneifolius, has been investigated as inhibitor of several human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms. By using superacid chemistry, analogues of the lactone phenolic hybrid lead compound have been synthesized and tested as CA inhibitors. Small chemical modifications of the basic scaffold revealed strong changes in the selectivity profile against different CA isoforms. These new compounds selectively inhibited isoforms CA I (KIs in the range of 0.13–0.76 μM), III (KIs in the range of 5.13–10.80 μM), XIII (KIs in the range of 0.34–0.96 μM) and XIV (KIs in the range of 2.44–7.24 μM), and can be considered as new leads, probably acting as non-zinc-binders, similar to other phenols/lactones investigated earlier. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect