A novel synthesized sulfonamido-based gallic acid – LDQN-C: Effects on chondrocytes growth and phenotype maintenance

Lu, Zhenhui; Wei, Shixiu; Wu, Huayu; Lin, Xiao; Lin, Cui-Wu; Liu, Buming; Zheng, Li; Zhao, Jinmin

doi:10.1016/j.bioorg.2014.09.005

Cited by 9 publications

(8 citation statements)

References 20 publications

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“…However, it exhibited an inhibitive effect on chondrocytes growth in the concentration between 0 and 40 μg/mL in a cytotoxicity assay, and therefore the subsequent experiments were not performed in this way. Nevertheless, other synthesized sulfonamido-based gallate analogues we had investigated previously [ 26 , 27 , 28 , 29 , 30 ] presented great effect on promoting chondrocyte growth and upregulating the expression of aggrecan, collagen II and Sox9, which confirm the fact that coupling of the phenyl ring with the sulfonamide group is critical for the pro-chondrogenic activity of these compounds and this docking model would provide us with a quick method to screen out the effective compounds. More docking studies should be performed in our further investigation to optimize their structures.…”

Section: Discussionmentioning

confidence: 65%

“…Recently, we have reported a series of synthesized sulfonamido-based gallates and their effectiveness on chondro-protection [ 26 , 27 , 28 , 29 , 30 ], which confirm the fact that coupling of the phenyl ring with the sulfonamide group is critical for the activity of preventing cartilage degeneration. Herein, another analog was synthesized and shown to be effective in biological evaluation, a docking study was therefore performed to provide an explanation for its activity and selectivity.…”

Section: Introductionmentioning

confidence: 80%

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

et al. 2016

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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.

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Section: Discussionmentioning

confidence: 65%

Section: Introductionmentioning

confidence: 80%

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

et al. 2016

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“…Nuti E and et al reported that compounds contained several phenyl groups and a sulfonamide group were effective in blocking ex vivo cartilage degradation without side effects on cytotoxicity [ 13 ]. Recently, we reported a new series of derivatives of GA synthesized by coupling with sulfonamides including sulfathiazole sodium, sulfadimidine, sulfachloropyrazine sodium and sulfamonomethoxine sodium [ 14 – 17 ]. These compounds were found to be effective in promoting proliferation and maintaining phenotype of chondrocytes.…”

Section: Introductionmentioning

confidence: 99%

A Novel Synthesized Sulfonamido-Based Gallate—JEZ-C as Potential Therapeutic Agents for Osteoarthritis

Wei

Zou

et al. 2015

PLoS ONE

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Gallic acid (GA) and its derivatives are anti-inflammatory agents reported to have an effect on osteoarthritis (OA). However, GA has much weaker anti-oxidant effects and inferior bioactivity compared with its derivatives. We modified GA with the introduction of sulfonamide to synthesize a novel compound named JEZ-C and analyzed its anti-arthritis and chondro-protective effects. Comparison of JEZ-C with its sources i.e. GA and Sulfamethoxazole (SMZ) was also performed. Results showed that JEZ-C could effectively inhibit the IL-1-mediated induction of MMP-1 and MMP-13 and could induce the expression of TIMP-1, which demonstrated its ability to reduce the progression of OA. JEZ-C can also exert chondro-protective effects by promoting cell proliferation and maintaining the phenotype of articular chondrocytes, as evidenced by improved cell growth, enhanced synthesis of cartilage specific markers such as aggrecan, collagen II and Sox9. Meanwhile, expression of the collagen I gene was effectively downregulated, revealing the inhibition of chondrocytes dedifferentiation by JEZ-C. Hypertrophy that may lead to chondrocyte ossification was also undetectable in JEZ-C groups. The recommended dose of JEZ-C ranges from 6.25×10-7 μg/ml to 6.25×10-5 μg/ml, among which the most profound response was observed with 6.25×10-6 μg/ml. In contrast, its source products of GA and SMZ have a weak effect not only in the inhibition of OA but also in the bioactivity of chondrocytes, which indicated the significance of this modification. This study revealed JEZ-C as a promising novel agent in the treatment of chondral and osteochondral lesions.

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“…34 The sulfachloropyridazines 6a,b were then obtained via deacetylation of 5a,b, applying an acid catalyzed reaction in tetrahydrofuran and methanol (Scheme 1). 33 It should be noted that compounds 5b 35 , 6a 36 and 6b 35 are known compounds but no carbonic anhydrase inhibition reported before.…”

Section: Resultsmentioning

confidence: 94%

“…24,25 Although, it was believed that amine group of sulphonamide should be primary to act as carbonic anhydrase inhibitor, recent studies indicated that secondary and even tertiary sulphonamides can act as affective carbonic anhydrase inhibitors and they can be selective. [26][27][28][29][30][31][32][33][34][35][36][37][38] showed that p-hydroxybenzoic acid had better inhibition properties on hCA I and hCA II compare with the natural product polyphenols and phenolic acids. 22 In this study, we reported secondary sulphonamides synthesized from p-hydroxybenzoic acid and 3,4,5-trihydroxybenzoic acid (Scheme 1), and investigated synergy of sulphonamides and polyphenols as carbonic anhydrase inhibitors on the hCA I and hCAII isozymes purified from human erythrocyte cells by Sepharose-4B-L-tyrosine-sulphanilamide.…”

Section: -7mentioning

confidence: 99%

Synthesis of some natural sulphonamide derivatives as carbonic anhydrase inhibitors

Gökçen¹,

Al²,

Topal³

et al. 2017

Org. Commun.

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Carbonic anhydrase inhibitors are both in clinical use as antiglaucoma, diuretics, antiepileptics and management of altitude sickness, and under investigation as anticancer, anticonvulsant and antiobesity agents. Sulphonamides have been known for decades as carbonic anhydrase inhibitors and are in clinical use. Sulphonamide derivatives of p-hydroxybenzoic acid and 3,4,5-trihydroxybenzoic acid (gallic acid) were synthesized and their inhibition values over hCA I and hCA II isozymes, purified from human erythrocyte cells by Sepharose-4B-L-tyrosine-sulphanilamide, were determined. Compounds synthesized showed efficient carbonic anhydrase inhibition activity at low nM levels.

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A novel synthesized sulfonamido-based gallic acid – LDQN-C: Effects on chondrocytes growth and phenotype maintenance

Cited by 9 publications

References 20 publications

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

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

A Novel Synthesized Sulfonamido-Based Gallate—JEZ-C as Potential Therapeutic Agents for Osteoarthritis

Synthesis of some natural sulphonamide derivatives as carbonic anhydrase inhibitors

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