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Molecules 2017, 22(1), 3;

Synthesis, Biological Evaluation, and Docking Studies of a Novel Sulfonamido-Based Gallate as Pro-Chondrogenic Agent for the Treatment of Cartilage

School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530005, China
Guangxi Key Laboratory of Traditional Chinese Medicine Quality Standards, Guangxi Institute of Traditional Medical and Pharmaceutical Sciences, Nanning 530022, China
The Medical and Scientific Research Center, Guangxi Medical University, Nanning 530021, China
These authors contributed equally to this work.
Author to whom correspondence should be addressed.
Academic Editor: Claudiu T. Supuran
Received: 9 October 2016 / Revised: 28 November 2016 / Accepted: 13 December 2016 / Published: 23 December 2016
(This article belongs to the Special Issue Sulfonamides)
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Gallic acid (GA) and its derivatives are anti-inflammatory agents and are reported to have potent effects on Osteoarthritis (OA) treatment. Nonetheless, it is generally accepted that the therapeutic effect and biocompatibility of GA is much weaker than its esters due to the high hydrophilicity. The therapeutic effect of GA on OA could be improved if certain structural modifications were made to increase its hydrophobicity. In this study, a novel sulfonamido-based gallate was synthesized by bonding sulfonamide with GA, and its biological evaluations on OA were investigated. Results show that 5-[4-(Pyrimidin-2-ylsulfamoylphenyl)]-carbamoyl-benzene-1,2,3-triyl triacetate (HAMDC) was able to reverse the effects induced by Interleukin-1 (IL-1) stimulation, and it also had a great effect on chondro-protection via promoting cell proliferation and maintaining the phenotype of articular chondrocytes, as well as enhancing synthesis of cartilage specific markers such as aggrecan, collagen II and Sox9. Furthermore, a docking study showed that HAMDC fits into the core of the active site of a disintegrin and metalloproteinase with thrombospondin motifs 5 (ADAMTS-5), which provides an explanation for its activity and selectivity. View Full-Text
Keywords: gallic acid; sulfadiazine sodium; pro-chondrogenic agent; molecular docking gallic acid; sulfadiazine sodium; pro-chondrogenic agent; molecular docking

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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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Lin, X.; Chai, L.; Liu, B.; Chen, H.; Zheng, L.; Liu, Q.; Lin, C. Synthesis, Biological Evaluation, and Docking Studies of a Novel Sulfonamido-Based Gallate as Pro-Chondrogenic Agent for the Treatment of Cartilage. Molecules 2017, 22, 3.

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