Click-tailed benzenesulfonamides as potent bacterial carbonic anhydrase inhibitors for targeting Mycobacterium tuberculosis and Vibrio cholerae.

Carbonic Anhydrase Inhibitors / chemical synthesis Carbonic Anhydrases / metabolism Click Chemistry Dose-Response Relationship, Drug Humans Molecular Structure Mycobacterium tuberculosis / enzymology Structure-Activity Relationship Sulfonamides / chemical synthesis Vibrio cholerae / enzymology Benzenesulfonamides
Anti-microbial Carbonic anhydrase Cholera Inhibition Sulfonamide Tuberculosis β-CAs

Journal

Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703

Informations de publication

Date de publication:
05 2019
Historique:
received: 03 12 2018
revised: 23 01 2019
accepted: 27 01 2019
pubmed: 5 2 2019
medline: 1 4 2020
entrez: 5 2 2019
Statut: ppublish

Résumé

A series of 1,2,3-triazole-bearing benzenesulfonamides was assessed for the inhibition of carbonic anhydrases (CA, EC 4.2.1.1) from bacteria Vibrio cholerae (VchCAα and VchCAβ) and Mycobacterium tuberculosis (β-mtCA3). Growing resistance phenomena against existing antimicrobial drugs are globally spreading and highlight a urgent need of agents endowed with alternative mechanisms of action. Two global WHO strategies aim to reduce cholera deaths by 90% and eradicate the tuberculosis epidemic by 2030. The derivatives here reported represent interesting leads towards the optimization of new antibiotic agents showing excellent inhibitory efficiency and selectivity for the target CAs over the human (h) off-target isoform hCA I. In detail, the first subset of derivatives potently inhibits VchCAα in a low nanomolar range (K

Identifiants

DOI: 10.1016/j.bioorg.2019.01.065 PMID: 30716618
pubmed: 30716618
pii: S0045-2068(18)31411-1
doi: 10.1016/j.bioorg.2019.01.065
pii:
doi:

Substances chimiques

Carbonic Anhydrase Inhibitors 0
Sulfonamides 0
Carbonic Anhydrases EC 4.2.1.1

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

183-186

Informations de copyright

Copyright © 2019 Elsevier Inc. All rights reserved.

Auteurs

Silvia Bua (S)

University of Florence, Department of Neuroscience, Psychology, Drug Research and Child's Health, Section of Pharmaceutical and Nutraceutical Sciences, via Ugo Schiff 6, 50019 Sesto Fiorentino, Italy.

Sameh M Osman (SM)

Department of Chemistry, College of Science, King Saud University, Riyadh, Saudi Arabia.

Sonia Del Prete (S)

Istituto di Bioscienze e Biorisorse, CNR, Napoli, Italy.

Clemente Capasso (C)

Istituto di Bioscienze e Biorisorse, CNR, Napoli, Italy.

Zeid AlOthman (Z)

Department of Chemistry, College of Science, King Saud University, Riyadh, Saudi Arabia.

Alessio Nocentini (A)

University of Florence, Department of Neuroscience, Psychology, Drug Research and Child's Health, Section of Pharmaceutical and Nutraceutical Sciences, via Ugo Schiff 6, 50019 Sesto Fiorentino, Italy. Electronic address: alessio.nocentini@unifi.it.

Claudiu T Supuran (CT)

University of Florence, Department of Neuroscience, Psychology, Drug Research and Child's Health, Section of Pharmaceutical and Nutraceutical Sciences, via Ugo Schiff 6, 50019 Sesto Fiorentino, Italy; Department of Chemistry, College of Science, King Saud University, Riyadh, Saudi Arabia. Electronic address: claudiu.supuran@unifi.it.

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Classifications MeSH

questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Mécanismes moléculaires de l'action pharmacologique › Antienzymes › Inhibiteurs de l'anhydrase carbonique › Click-tailed benzenesulfonamides as potent...
questionsmedicales.fr › Enzymes et coenzymes › Enzymes › Lyases › Carbon-oxygen lyases › Hydro-lyases › Carbonic anhydrases › Click-tailed benzenesulfonamides as potent...
questionsmedicales.fr › Technologie, industrie et agriculture › Technologie › Technologie pharmaceutique › Techniques de chimie synthétique › Chimie click › Click-tailed benzenesulfonamides as potent...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes toxicologiques › Relation dose-effet des médicaments › Click-tailed benzenesulfonamides as potent...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Primates › Haplorhini › Catarrhini › Hominidae › Humains › Click-tailed benzenesulfonamides as potent...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Click-tailed benzenesulfonamides as potent...
questionsmedicales.fr › Bactéries › Bactéries à Gram positif › Bâtonnets à Gram positif › Bâtonnets asporogènes à Gram positif › Bâtonnets asporogènes réguliers à Gram positif › Mycobacteriaceae › Mycobacterium › Mycobacterium tuberculosis › Click-tailed benzenesulfonamides as potent...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes pharmacologiques › Relation structure-activité › Click-tailed benzenesulfonamides as potent...
questionsmedicales.fr › Composés chimiques organiques › Composés du soufre › Sulfones › Sulfonamides › Click-tailed benzenesulfonamides as potent...
questionsmedicales.fr › Bactéries › Proteobacteria › Gammaproteobacteria › Vibrionaceae › Vibrio › Vibrio cholerae › Click-tailed benzenesulfonamides as potent...