Sulfonyl phosphonic 1,4-dithia-7-azaspiro[4,4]nonane derivatives as matrix metalloproteinase inhibitors: Synthesis, a docking study, and biological evaluation

Zhang, Hao; Li, Xuan; Wang, Xuejian; Xu, Wenfang; Zhang, Jian

doi:10.5582/ddt.2017.01016

Cited by 2 publications

(2 citation statements)

References 23 publications

(28 reference statements)

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“…Since compounds MH1-18 and MH1-21 had the best HDACs inhibitory activity, they were evaluated in an MTT assay to determine their antiproliferative effect on human cancer cell line SGC-7901 (gastric cancer), NCI-H226 (lung squamous cell cancer), MCF-module and optimized using Powell's method with the Tripos force field with convergence criterion set at 0.05 kcal/(Å mol) and assigned charges with the Gasteiger_ Hückel method (27). Molecular docking was carried out via the Sybyl/SurflexDock module.…”

Section: In Vitro Antiproliferative Activity Of Compounds Mh1-18 and mentioning

confidence: 99%

Design, synthesis and biological evaluation of 4-piperidin-4-yl-triazole derivatives as novel histone deacetylase inhibitors

Gao

Mou

et al. 2019

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Acetylation as one of the most important covalent modification manners in the field of epigenetics, the level of it is taken control of by two families of enzymes with opposite mechanisms, histone acetyltransferases (HATs) and histone deacetylases (HDACs). HDACs are responsible for removal of the acetyl group from lysine residues in histones and non-histone substrates (1). Till now, 18 isoforms of HDACs have been discovered, and they are divided into four categories based on their sequence similarity and functions: class I (HDAC1, 2, Summary Histone deacetylase is an important member of epigenetics and a well validated target for anti-cancer drug discovery. In this study, we designed and synthesized a series of twenty-one novel hydroxamic acid-based histone deacetylase inhibitors with 4-piperidin-4-yl-triazole as the core skeleton. Most target compounds displayed excellent inhibition rates toward histone deacetylases at the concentration of 1 μM. Among them, the inhibition rates of two compounds MH1-18 and MH1-21 exceeded 90%. Furthermore, these two compounds selectively inhibited the activity of histone deacetylase 6 with low IC 50 values. The high potency of them toward histone deacetylase 6 was rationalized by molecular docking studies. We found that MH1-18 and MH1-21 moderately inhibited the proliferation of four human cancer cell lines SGC-7901, NCI-H226, MCF-7, and HL-60. However, MH1-21 showed potent efficacy in suppressing the migration of MCF-7 cells. Results obtained in the current study shed light on designing potent HDAC6 inhibitors as anti-cancer agents.

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Section: In Vitro Antiproliferative Activity Of Compounds Mh1-18 and mentioning

confidence: 99%

Design, synthesis and biological evaluation of 4-piperidin-4-yl-triazole derivatives as novel histone deacetylase inhibitors

Gao

Mou

et al. 2019

BST

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“…Some have reached the stage of an advanced clinical trial, as exemplified by CGS 27023A, prinomastat, and ilomastat (7,8). Colleagues of the current authors have previously reported several kinds of synthetic MMP inhibitors, such as caffeoyl pyrrolidine derivatives (9), sulfonyl pyrrolidine derivatives (10), quinoxalinone peptidomimetic derivatives (11), Pro-Gly peptidomimetic derivatives (12), and phosphonic 1,4-dithia-7-azaspiro [4,4] nonane derivatives (13).…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and biological evaluation of 4-phenoxybenzenesulfonyl pyrrolidine derivatives as matrix metalloproteinase inhibitors

Mao

Zhang

Wang

et al. 2020

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Sulfonyl phosphonic 1,4-dithia-7-azaspiro[4,4]nonane derivatives as matrix metalloproteinase inhibitors: Synthesis, a docking study, and biological evaluation

Cited by 2 publications

References 23 publications

Design, synthesis and biological evaluation of 4-piperidin-4-yl-triazole derivatives as novel histone deacetylase inhibitors

Design, synthesis and biological evaluation of 4-piperidin-4-yl-triazole derivatives as novel histone deacetylase inhibitors

Design, synthesis, and biological evaluation of 4-phenoxybenzenesulfonyl pyrrolidine derivatives as matrix metalloproteinase inhibitors

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