On the intrinsic reactivity of highly potent trypanocidal cruzain inhibitors.


Journal

RSC medicinal chemistry
ISSN: 2632-8682
Titre abrégé: RSC Med Chem
Pays: England
ID NLM: 101759460

Informations de publication

Date de publication:
18 Nov 2020
Historique:
received: 28 03 2020
accepted: 03 08 2020
entrez: 7 6 2021
pubmed: 8 6 2021
medline: 8 6 2021
Statut: epublish

Résumé

The cysteine protease cruzipain is considered to be a validated target for therapeutic intervention in the treatment of Chagas disease. Hence, peptidomimetic cruzipain inhibitors having a reactive group (known as warhead) are subject to continuous studies to discover novel antichagasic compounds. Here, we evaluated how different warheads for a set of structurally similar related compounds could inhibit the activity of cruzipain and, ultimately, their trypanocidal effect. We first investigated

Identifiants

pubmed: 34095840
doi: 10.1039/d0md00097c
pii: d0md00097c
pmc: PMC8126975
doi:

Types de publication

Journal Article

Langues

eng

Pagination

1275-1284

Informations de copyright

This journal is © The Royal Society of Chemistry.

Déclaration de conflit d'intérêts

The authors declare no conflict of interest.

Références

Phys Chem Chem Phys. 2018 Sep 26;20(37):24317-24328
pubmed: 30211406
Bioorg Chem. 2018 Sep;79:285-292
pubmed: 29783099
J Chem Theory Comput. 2012 Apr 10;7(4):931-948
pubmed: 23204947
Phys Rev B Condens Matter. 1988 Jan 15;37(2):785-789
pubmed: 9944570
Mol Biochem Parasitol. 2001 Apr 25;114(1):41-52
pubmed: 11356512
Bioorg Med Chem Lett. 2009 Feb 15;19(4):1136-8
pubmed: 19168354
Eur J Med Chem. 2018 Dec 5;160:94-107
pubmed: 30321804
Spectrochim Acta A Mol Biomol Spectrosc. 2018 Jan 5;188:537-546
pubmed: 28759855
Bioorg Med Chem. 2004 Nov 1;12(21):5533-43
pubmed: 15465330
Angew Chem Int Ed Engl. 2008;47(23):4331-4
pubmed: 18404765
J Venom Anim Toxins Incl Trop Dis. 2013 Dec 19;19(1):34
pubmed: 24354455
Mem Inst Oswaldo Cruz. 2014 Sep;109(6):828-33
pubmed: 25317712
PLoS Negl Trop Dis. 2015 Jul 14;9(7):e0003916
pubmed: 26173110
Biochemistry. 2017 Jun 27;56(25):3178-3183
pubmed: 28621541
Drug Metab Rev. 2014 Feb;46(1):96-123
pubmed: 24171394
J Biol Chem. 1988 Nov 25;263(33):17205-8
pubmed: 3053703
Science. 2020 Jun 19;368(6497):1331-1335
pubmed: 32321856
Bioorg Med Chem Lett. 2007 Feb 15;17(4):998-1002
pubmed: 17157022
Nature. 2010 Jun 24;465(7301):S6-7
pubmed: 20571554
PLoS Negl Trop Dis. 2017 Feb 21;11(2):e0005343
pubmed: 28222138
Trop Med Int Health. 2014 Feb;19(2):212-8
pubmed: 24299280
Bioorg Med Chem Lett. 2017 Nov 15;27(22):5031-5035
pubmed: 29054358
J Med Chem. 2019 Dec 12;62(23):10497-10525
pubmed: 31361135
J Chem Inf Model. 2020 Mar 23;60(3):1666-1677
pubmed: 32126170
J Chem Inf Model. 2019 Aug 26;59(8):3565-3571
pubmed: 31246457
Comput Biol Chem. 2018 Aug;75:91-100
pubmed: 29753268
J Biomol Screen. 2015 Jan;20(1):22-35
pubmed: 25245987
Bioorg Med Chem. 2019 Nov 15;27(22):115083
pubmed: 31561938
J Org Chem. 2012 Jan 6;77(1):90-5
pubmed: 22126265
Bioorg Med Chem. 2019 May 15;27(10):2066-2074
pubmed: 30975501
J Am Chem Soc. 1986 Sep 1;108(19):5708-11
pubmed: 22175316
Clin Microbiol Rev. 2011 Oct;24(4):655-81
pubmed: 21976603
J Mol Biol. 1995 Mar 24;247(2):251-9
pubmed: 7707373
Org Biomol Chem. 2012 Aug 14;10(30):5764-8
pubmed: 22336919
Chem Rev. 2006 Jun;106(6):2065-91
pubmed: 16771443
J Chem Inf Model. 2017 Dec 26;57(12):3124-3137
pubmed: 29131621
J Org Chem. 2003 Jul 25;68(15):5886-9
pubmed: 12868922
J Med Chem. 2014 Jun 26;57(12):4977-5010
pubmed: 24351051
Chem Res Toxicol. 2014 Jul 21;27(7):1081-91
pubmed: 24911545
ACS Med Chem Lett. 2015 Dec 15;7(1):77-82
pubmed: 26819670
J Med Chem. 2019 Jun 27;62(12):5673-5724
pubmed: 30565923
Acta Trop. 2014 Nov;139:57-66
pubmed: 25017312

Auteurs

Vinicius Bonatto (V)

Medicinal Chemistry Group, Institute of Chemistry of São Carlos, University of São Paulo Avenue Trabalhador Sancarlense, 400 23566-590 São Carlos/SP Brazil andreileitao@iqsc.usp.br carlos.montanari@usp.br.

Pedro Henrique Jatai Batista (PHJ)

Medicinal Chemistry Group, Institute of Chemistry of São Carlos, University of São Paulo Avenue Trabalhador Sancarlense, 400 23566-590 São Carlos/SP Brazil andreileitao@iqsc.usp.br carlos.montanari@usp.br.

Lorenzo Cianni (L)

Medicinal Chemistry Group, Institute of Chemistry of São Carlos, University of São Paulo Avenue Trabalhador Sancarlense, 400 23566-590 São Carlos/SP Brazil andreileitao@iqsc.usp.br carlos.montanari@usp.br.

Daniela De Vita (D)

Medicinal Chemistry Group, Institute of Chemistry of São Carlos, University of São Paulo Avenue Trabalhador Sancarlense, 400 23566-590 São Carlos/SP Brazil andreileitao@iqsc.usp.br carlos.montanari@usp.br.

Daniel G Silva (DG)

Medicinal Chemistry Group, Institute of Chemistry of São Carlos, University of São Paulo Avenue Trabalhador Sancarlense, 400 23566-590 São Carlos/SP Brazil andreileitao@iqsc.usp.br carlos.montanari@usp.br.

Rodrigo Cedron (R)

Medicinal Chemistry Group, Institute of Chemistry of São Carlos, University of São Paulo Avenue Trabalhador Sancarlense, 400 23566-590 São Carlos/SP Brazil andreileitao@iqsc.usp.br carlos.montanari@usp.br.

Daiane Y Tezuka (DY)

Medicinal Chemistry Group, Institute of Chemistry of São Carlos, University of São Paulo Avenue Trabalhador Sancarlense, 400 23566-590 São Carlos/SP Brazil andreileitao@iqsc.usp.br carlos.montanari@usp.br.
Ribeirão Preto School of Pharmaceutical Sciences, University of São Paulo Ribeirão Preto São Paulo Brazil.

Sérgio de Albuquerque (S)

Ribeirão Preto School of Pharmaceutical Sciences, University of São Paulo Ribeirão Preto São Paulo Brazil.

Carolina Borsoi Moraes (CB)

Laboratório Nacional de Biociências (LNBio), Centro Nacional de Pesquisa em Energia e Materiais (CNPEM) Campinas São Paulo Brazil.

Caio Haddad Franco (CH)

Laboratório Nacional de Biociências (LNBio), Centro Nacional de Pesquisa em Energia e Materiais (CNPEM) Campinas São Paulo Brazil.

Jerônimo Lameira (J)

Medicinal Chemistry Group, Institute of Chemistry of São Carlos, University of São Paulo Avenue Trabalhador Sancarlense, 400 23566-590 São Carlos/SP Brazil andreileitao@iqsc.usp.br carlos.montanari@usp.br.
Laboratório de Planejamento e Desenvolvimento de Fármacos, Instituto de Ciências Exatas e Naturais, Universidade Federal do Pará Rua Augusto Corrêa 01 CP 66075-110 Belém-PA Brazil.

Andrei Leitão (A)

Medicinal Chemistry Group, Institute of Chemistry of São Carlos, University of São Paulo Avenue Trabalhador Sancarlense, 400 23566-590 São Carlos/SP Brazil andreileitao@iqsc.usp.br carlos.montanari@usp.br.

Carlos A Montanari (CA)

Medicinal Chemistry Group, Institute of Chemistry of São Carlos, University of São Paulo Avenue Trabalhador Sancarlense, 400 23566-590 São Carlos/SP Brazil andreileitao@iqsc.usp.br carlos.montanari@usp.br.

Classifications MeSH