Chemoselective Synthesis and Anti-Kinetoplastidal Properties of 2,6-Diaryl-4H-tetrahydro-thiopyran-4-one S-Oxides: Their Interplay in a Cascade of Redox Reactions from Diarylideneacetones.
Gendron, Thibault; Lanfranchi, Don Antoine; Wenzel, Nicole Iet al.
[en] 2,6-Diaryl-4H-tetrahydro-thiopyran-4-ones and corresponding sulfoxide and sulfone derivatives were designed to lower the major toxicity of their parent anti-kinetoplatidal diarylideneacetones through a prodrug effect. Novel diastereoselective methodologies were developed and generalized from diarylideneacetones and 2,6-diaryl-4H-tetrahydro-thiopyran-4-ones to allow the introduction of a wide substitution profile and to prepare the related S-oxides. The in vitro biological activity and selectivity of diarylideneacetones, 2,6-diaryl-4H-tetrahydro-thiopyran-4-ones, and their S-sulfoxide and sulfone metabolites were evaluated against Trypanosoma brucei brucei, Trypanosoma cruzi, and various Leishmania species in comparison with their cytotoxicity against human fibroblasts hMRC-5. The data revealed that the sulfides, sulfoxides, and sulfones, in which the Michael acceptor sites are temporarily masked, are less toxic against mammal cells while the anti-trypanosomal potency was maintained against T. b. brucei, T. cruzi, L. infantum, and L. donovani, thus confirming the validity of the prodrug strategy. The mechanism of action is proposed to be due to the involvement of diarylideneacetones in cascades of redox reactions involving the trypanothione system. After Michael addition of the dithiol to the double bonds, resulting in an elongated polymer, the latter-upon S-oxidation, followed by syn-eliminations-fragments, under continuous release of reactive oxygen species and sulfenic/sulfonic species, causing the death of the trypanosomal parasites in the micromolar or submicromolar range with high selectivity indexes.
Disciplines :
Chemistry
Author, co-author :
Gendron, Thibault ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie organique-nucléaire ; UMR7042 Université de Strasbourg-CNRS-UHA, Laboratoire d'Innovation Moléculaire et Applications (LIMA), Team Bio(IN)organic and Medicinal Chemistry, European School of Chemistry, Polymers and Materials (ECPM), 25 Rue Becquerel, F-67087 Strasbourg, France
Lanfranchi, Don Antoine; UMR7042 Université de Strasbourg-CNRS-UHA, Laboratoire d'Innovation Moléculaire et Applications (LIMA), Team Bio(IN)organic and Medicinal Chemistry, European School of Chemistry, Polymers and Materials (ECPM), 25 Rue Becquerel, F-67087 Strasbourg, France
Wenzel, Nicole I ; Bioorganic & Medicinal Chemistry Laboratory, Biochemie-Zentrum, Heidelberg University, Im Neuenheimer Feld 504, D-69120 Heidelberg, Germany
Kessedjian, Hripsimée; UMR7042 Université de Strasbourg-CNRS-UHA, Laboratoire d'Innovation Moléculaire et Applications (LIMA), Team Bio(IN)organic and Medicinal Chemistry, European School of Chemistry, Polymers and Materials (ECPM), 25 Rue Becquerel, F-67087 Strasbourg, France
Maes, Louis ; Laboratory of Microbiology, Parasitology and Hygiene (LMPH), Faculty of Pharmaceutical, Biomedical and Veterinary Sciences, University of Antwerp, Universiteitsplein 1, B-2610 Antwerp, Belgium
Cojean, Sandrine; Antiparasitic Chemotherapy, Faculty of Pharmacy, BioCIS, UMR 8076 Université Paris-Saclay-CNRS 17, Rue des Sciences, F-91400 Orsay, France
Müller, Thomas J J ; Institut für Organische Chemie und Makromolekulare Chemie, Mathematisch-Naturwissenschaftliche FakultätFakultät, Heinrich-Heine-Universität Düsseldorf, Universitätsstraße 1, D-40225 Düsseldorf, Germany
Loiseau, Philippe M ; Antiparasitic Chemotherapy, Faculty of Pharmacy, BioCIS, UMR 8076 Université Paris-Saclay-CNRS 17, Rue des Sciences, F-91400 Orsay, France
Davioud-Charvet, Elisabeth ; UMR7042 Université de Strasbourg-CNRS-UHA, Laboratoire d'Innovation Moléculaire et Applications (LIMA), Team Bio(IN)organic and Medicinal Chemistry, European School of Chemistry, Polymers and Materials (ECPM), 25 Rue Becquerel, F-67087 Strasbourg, France
Language :
English
Title :
Chemoselective Synthesis and Anti-Kinetoplastidal Properties of 2,6-Diaryl-4H-tetrahydro-thiopyran-4-one S-Oxides: Their Interplay in a Cascade of Redox Reactions from Diarylideneacetones.
Publication date :
04 April 2024
Journal title :
Molecules
eISSN :
1420-3049
Publisher :
Multidisciplinary Digital Publishing Institute (MDPI), Switzerland
DFG - Deutsche Forschungsgemeinschaft [DE] MESRI - Ministère de l’Enseignement supérieur, de la Recherche et de l’Innovation [FR]
Funding text :
This work was partly supported by the Laboratoire d\u2019Excellence ParaFrap (grant LabEx ParaFrap ANR-11-LABX-0024 (E.D.-C. in Strasbourg, France) and the DFG via the SFB 544 (B14 project, N.I. W.\u2019s salary) when E.D.C. was a delegate of the Centre National de la Recherche Scientifique in Biochemie-Zentrum, in the frame of a French\u2013German cooperation with Heidelberg University, Germany. T.G. is grateful to Strasbourg University for his doctoral fellowship from the French Ministry of Higher Education, Research and Innovation (France) (MESRI).
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