Synthesis and evaluation of heterocycle structures as potential inhibitors of Mycobacterium tuberculosis UGM

Carine Maaliki; Jian Fu; Sydney Villaume; Albertus Viljoen; Clément Raynaud; Sokaina Hammoud; Jérôme Thibonnet; Laurent Kremer; Stéphane P. Vincent; Emilie Thiery

doi:10.1016/j.bmc.2020.115579

Synthesis and evaluation of heterocycle structures as potential inhibitors of Mycobacterium tuberculosis UGM

Carine Maaliki, Jian Fu, Sydney Villaume, Albertus Viljoen, Clément Raynaud, Sokaina Hammoud, Jérôme Thibonnet, Laurent Kremer, Stéphane P. Vincent, Emilie Thiery

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Abstract

In this study, we screen three heterocyclic structures as potential inhibitors of UDP-galactopyranose mutase (UGM), an enzyme involved in the biosynthesis of the cell wall of Mycobacterium tuberculosis. In order to understand the binding mode, docking simulations are performed on the best inhibitors. Their activity on Mycobacterium tuberculosis is also evaluated. This study made it possible to highlight an “oxazepino-indole” structure as a new inhibitor of UGM and of M. tuberculosis growth in vitro.

Original language	English
Article number	115579
Journal	Bioorganic and Medicinal Chemistry
Volume	28
Issue number	13
DOIs	https://doi.org/10.1016/j.bmc.2020.115579
Publication status	Published - 1 Jul 2020

Keywords

Docking
Heterocycles
Inhibitor
Mycobacterium tuberculosis
UDP-galactopyranose mutase

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.bmc.2020.115579

1-s2.0-S0968089620304090-mainFinal published version, 1.23 MBLicence: CC BY-NC-ND

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title = "Synthesis and evaluation of heterocycle structures as potential inhibitors of Mycobacterium tuberculosis UGM",

abstract = "In this study, we screen three heterocyclic structures as potential inhibitors of UDP-galactopyranose mutase (UGM), an enzyme involved in the biosynthesis of the cell wall of Mycobacterium tuberculosis. In order to understand the binding mode, docking simulations are performed on the best inhibitors. Their activity on Mycobacterium tuberculosis is also evaluated. This study made it possible to highlight an “oxazepino-indole” structure as a new inhibitor of UGM and of M. tuberculosis growth in vitro.",

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note = "Funding Information: This study was supported by the Fondation pour la Recherche M{\'e}dicale (grant DEQ20150331719 to L.K.), the Association Gregory Lemarchal and Vaincre la Mucoviscidose (grant RIF20180502320 to C.R.) The University of Namur (PhD grant to SV) and China Scholarship Council (PhD grant to JF). We acknowledge the French Ministry for Research and Innovation for the financial support and Dr. Fr{\'e}d{\'e}ric Montigny (Analysis Department, Tours University) for HRMS. Publisher Copyright: {\textcopyright} 2020 Elsevier Ltd",

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T1 - Synthesis and evaluation of heterocycle structures as potential inhibitors of Mycobacterium tuberculosis UGM

AU - Maaliki, Carine

AU - Fu, Jian

AU - Villaume, Sydney

AU - Viljoen, Albertus

AU - Raynaud, Clément

AU - Hammoud, Sokaina

AU - Thibonnet, Jérôme

AU - Kremer, Laurent

AU - Vincent, Stéphane P.

AU - Thiery, Emilie

N1 - Funding Information: This study was supported by the Fondation pour la Recherche Médicale (grant DEQ20150331719 to L.K.), the Association Gregory Lemarchal and Vaincre la Mucoviscidose (grant RIF20180502320 to C.R.) The University of Namur (PhD grant to SV) and China Scholarship Council (PhD grant to JF). We acknowledge the French Ministry for Research and Innovation for the financial support and Dr. Frédéric Montigny (Analysis Department, Tours University) for HRMS. Publisher Copyright: © 2020 Elsevier Ltd

PY - 2020/7/1

Y1 - 2020/7/1

N2 - In this study, we screen three heterocyclic structures as potential inhibitors of UDP-galactopyranose mutase (UGM), an enzyme involved in the biosynthesis of the cell wall of Mycobacterium tuberculosis. In order to understand the binding mode, docking simulations are performed on the best inhibitors. Their activity on Mycobacterium tuberculosis is also evaluated. This study made it possible to highlight an “oxazepino-indole” structure as a new inhibitor of UGM and of M. tuberculosis growth in vitro.

AB - In this study, we screen three heterocyclic structures as potential inhibitors of UDP-galactopyranose mutase (UGM), an enzyme involved in the biosynthesis of the cell wall of Mycobacterium tuberculosis. In order to understand the binding mode, docking simulations are performed on the best inhibitors. Their activity on Mycobacterium tuberculosis is also evaluated. This study made it possible to highlight an “oxazepino-indole” structure as a new inhibitor of UGM and of M. tuberculosis growth in vitro.

KW - Docking

KW - Heterocycles

KW - Inhibitor

KW - Mycobacterium tuberculosis

KW - UDP-galactopyranose mutase

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VL - 28

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

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M1 - 115579

ER -

Synthesis and evaluation of heterocycle structures as potential inhibitors of Mycobacterium tuberculosis UGM

Abstract

Keywords

UN SDGs

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