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Molecules 2018, 23(2), 415; https://doi.org/10.3390/molecules23020415

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.
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)
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Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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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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