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Open AccessArticle

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

1
Department of Food and Drug, University of Parma, Parco Area delle Scienze 27/A, 43124 Parma, Italy
2
Department of Drug Sciences, University of Catania, V. le A. Doria 6, 95125 Catania, Italy
3
Pharmaceutical Chemistry Department, Faculty of Pharmacy, Ankara University, Tandogan, Ankara 06100, Turkey
4
Department of Physiological Sciences, University of Catania, V. le A. Doria 6, 95125 Catania, Italy
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(2), 415; https://doi.org/10.3390/molecules23020415
Received: 30 October 2017 / Revised: 1 February 2018 / Accepted: 3 February 2018 / Published: 14 February 2018
(This article belongs to the Special Issue Recent Trends on Enzymes Inhibitors and Activators in Drug Research)
Nine 2-(1,2-benzothiazol-3-yl)-N-(4-oxo-2-phenyl-1,3-thiazolidin-3-yl)propanamides combining a benzisothiazole and 4-thiazolidinone in one framework were designed and synthesized. The aim of the study was to verify their effectiveness to affect the inflammatory/oxidative process in which free oxygen and nitrite (ROS and RNS) radicals, inflammatory mediators, such as nuclear factor κB (NF-κB), 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/potential 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). View Full-Text
Keywords: 4-thiazolidinones; ORAC assay; metalloproteinase-9; docking study; keratinocytes cultures; nuclear factor-κB 4-thiazolidinones; ORAC assay; metalloproteinase-9; docking study; keratinocytes cultures; nuclear factor-κB
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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.

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