当前位置： SCI文献检索 > JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY期刊下所有文献 > Synthesis and biological evaluation of thiazolidinedione derivatives with high ligand efficiency to P. aeruginosa PhzS.

Synthesis and biological evaluation of thiazolidinedione derivatives with high ligand efficiency to P. aeruginosa PhzS.

Abstract：

:The thiazolidinone ring is found in compounds that have widespan biology activity and there is mechanism-based evidence that compounds bearing this moiety inhibit P. aeruginosa PhzS (PaPzhS), a key enzyme in the biosynthesis of the virulence factor named pyocyanin. Ten novel thiazolidinone derivatives were synthesised and screened against PaPhzS, using two orthogonal assays. The biological results provided by these and 28 other compounds, whose synthesis had been described, suggest that the dihydroquinazoline ring, found in the previous hit (A- Kd = 18 µM and LE = 0.20), is not required for PaPzhS inhibition, but unsubstituted nitrogen at the thiazolidinone ring is. The molecular simplification approach, pursued in this work, afforded an optimised lead compound (13- 5-(2,4-dimethoxyphenyl)thiazolidine-2,4-dione) with 10-fold improvement in affinity (Kd= 1.68 µM) and more than 100% increase in LE (0.45), which follows the same inhibition mode as the original hit compound (competitive to NADH).Executive summaryPhzS is a key enzyme in the pyocyanin biosynthesis pathway in P. aeruginosa.Orthogonal assays (TSA and FITC) show that fragment-like thiazolidinedione derivatives bind to PaPhzS with one-digit micromolar affinity.Fragment-like thiazolidinedione derivatives bind to the cofactor (NADH) binding site in PaPhzS.The molecular simplification optimised the ligand efficiency and affinity of the lead compound.

journal_name

J Enzyme Inhib Med Chem

journal_title

Journal of enzyme inhibition and medicinal chemistry

authors

Froes TQ,Chaves BT,Mendes MS,Ximenes RM,da Silva IM,da Silva PBG,de Albuquerque JFC,Castilho MS

doi

10.1080/14756366.2021.1931165

keywords:

["P. aeruginosa","Thiazolidinone","antimicrobial resistance","pyocyanin biosynthesis inhibition"]

subject

Has Abstract

pub_date

2021-12-01 00:00:00

pages

1217-1229

issue

1

eissn

1475-6366

issn

1475-6374

journal_volume

36

pub_type

杂志文章

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