2-Benzisothiazolylimino-5-benzylidene-4-thiazolidinones as protective agents against cartilage destruction

Bioorganic & Medicinal Chemistry
Lucia CrascìA M Panico

Abstract

We report the synthesis, the antioxidant and the inhibitory activity (IC50) on metalloproteinases (MMPs) 3 and 13 of 2-benzo[d]isothiazolylimino-5-benzylidene-4-thiazolidinones. Their potential as protective agents in osteoarthritis (OA) was evaluated by biological assays on chondrocytes cultures, stimulated by IL-1β. The chondroprotective capability, related both to antioxidant activity and to inhibition of MMPs, was studied in vitro, by determining nitric oxide production and glycosaminoglycans release. Moreover, selected derivatives 1h and 1g was studied for nuclear factor kappaB (NF-κB) inhibition by Western Blot analysis and for MMP-3 protein release using ELISA test. The structure-activity relationship of tested compounds demonstrates a favorable effect of the para substitution on the 5-benzilydene ring. Compound 1g shows a potent and selective activity on MMP-3 versus MMP-13. Accordingly, 1g possesses high antioxidant effect, NO lowering and GAGs restoring capability and also reduces the production of MMPs and NF-κB expression. Thus 1g can be considered as new potential chondroprotective agents.

References

Jan 24, 2013·Therapeutic Advances in Chronic Disease·Evan Meszaros, Charles J Malemud
Sep 6, 2013·The International Journal of Biochemistry & Cell Biology·Stella Rigoglou, Athanasios G Papavassiliou

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Citations

Apr 19, 2016·European Journal of Medicinal Chemistry·Julia SenkivRoman Lesyk
Feb 15, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Matteo IncertiAnnamaria Panico
Oct 27, 2017·Current Medicinal Chemistry·Ana Cristina Lima LeiteGevanio Bezerra de Oliveira Filho

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