Preprint Article Version 1 This version not peer reviewed

4-Thiazolidinone Derivatives as MMP Inhibitors in Tissue Damage: Synthesis, Biological Evaluation and Docking Studies

Version 1 : Received: 30 October 2017 / Approved: 31 October 2017 / Online: 31 October 2017 (16:36:16 CET)

A peer-reviewed article of this Preprint also exists.

Incerti, M.; Crascì, L.; Vicini, P.; Aki, E.; Yalcin, I.; Ertan-Bolelli, T.; Cardile, V.; Graziano, A.C.E.; Panico, A. 4-Thiazolidinone Derivatives as MMP Inhibitors in Tissue Damage: Synthesis, Biological Evaluation and Docking Studies. Molecules 2018, 23, 415. Incerti, M.; Crascì, L.; Vicini, P.; Aki, E.; Yalcin, I.; Ertan-Bolelli, T.; Cardile, V.; Graziano, A.C.E.; Panico, A. 4-Thiazolidinone Derivatives as MMP Inhibitors in Tissue Damage: Synthesis, Biological Evaluation and Docking Studies. Molecules 2018, 23, 415.

Journal reference: Molecules 2018, 23, 415
DOI: 10.3390/molecules23020415

Abstract

Nine 2-(1,2-benzothiazol-3-yl)-N-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl) propanamides were designed and synthesized, combining benzisothiazole and 4-thiazolidinone in one frame. The aim of the study was to verify their effectiveness to contrast  the inflammatory/oxidative  process  in which  free oxygen and nitrite (ROS and RNS) radicals, advanced glycation products (AGEs), inflammatory cytokines and matrix metalloproteinases (MMPs) are involved. Docking studies of all the compounds were performed in order to explore their binding mode at the MMP-9 protein.  An appreciable anti-inflammatory/wound healing effects of the tested compounds was highlighted. Derivative 23, bearing a 4-carboxyphenyl substituent at C2 of the 4-thiazolidinone ring, exhibited the highest activity, being able to inhibit MMP-9 at nanomolar level  (IC50  = 40 nM).

Subject Areas

4-Thiazolidinones; ORAC assay; Metalloproteinase-9; Docking study; Keratinocytes cultures; Nuclear factor -kB.

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