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Type:	Artigo de Periódico
Title:	Ionic liquid-assisted synthesis of dihydropyrimidin(thi)ones biginelli adducts and investigation of their mechanism of urease inhibition
Authors:	Taniris Cafiero Braga Ângelo de Fátima Thamara Ferreira Silva Thamilla Maria Silva Maciel Edjan Carlos Dantas da Silva Edeildo Ferreira da Silva-Júnior Luzia Valentina Modolo Isis Martins Figueiredo Josué Carinhanha Caldas Santos Thiago Mendonça de Aquino
Abstract:	Twenty-six Biginelli adducts were synthesized through an ionic liquid-assisted synthesis with up to 92% yield. Sixteen of these Biginelli adducts were then assayed to determine their antiureolytic activity against purified urease from jack beans. The substances BA7-S, BA9-S and BA11-S were shown to be as efficient inhibitors as hydroxyurea, a positive control used in in vitro screening assay against urease. Fluorescence studies revealed that BA7-S, BA9-S, BA11-S and BA5-S possessed high binding constant values of 5.95, 6.72, 4.55, and 4.28 M−1, respectively, while BAS12-S, without substituents, showed a low value of log Kb = 2.16 M−1. In addition, in the most thermodynamically favorable BA5-S and BA7-S urease complexes, the corresponding Biginelli adducts were capable of interacting with the active site of urease through non-ionic interactions, such as hydrophobic interactions, or hydrogen and van der Waals interactions, respectively. In silico studies also supported that the BAs interact with the active site, confirming the fluorescence and kinetic assay studies, which clearly indicate that BA5-S and BA7-S are competitive inhibitors (Ki = 0.96 and 0.57 mM, respectively). In silico studies also showed that the substituents in the aromatic ring interact with Ni atoms to form a stable complex.
Subject:	Química Urease - Inibidores Fluorescência
language:	eng
metadata.dc.publisher.country:	Brasil
Publisher:	Universidade Federal de Minas Gerais
Publisher Initials:	UFMG
metadata.dc.publisher.department:	ICB - DEPARTAMENTO DE BOTÂNICA ICX - DEPARTAMENTO DE QUÍMICA
Rights:	Acesso Restrito
metadata.dc.identifier.doi:	https://doi.org/10.1039/C9NJ03556G
URI:	http://hdl.handle.net/1843/76025
Issue Date:	2019
metadata.dc.url.externa:	https://pubs.rsc.org/en/content/articlelanding/2019/nj/c9nj03556g#!
metadata.dc.relation.ispartof:	New Journal of Chemistry
Appears in Collections:	Artigo de Periódico

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