Design, synthesis and antiproliferative activity studies of novel 1,2,3-triazole–dithiocarbamate–urea hybrids

Duan, Ying-Chao; Zheng, Yi-Chao; Li, Xiaochen; Wang, Mengmeng; Ye, Xian-Wei; Guan, Yu; Liu, Gai-Zhi; Zheng, Jiaxin; Liu, Hong‐Min

doi:10.1016/j.ejmech.2013.03.058

Cited by 99 publications

(20 citation statements)

References 56 publications

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“…Apoptosis is a distinctive and important mode of programmed cell death, which involves the elimination of abnormal cells in development and tissue homeostasis. The most imperative mode of action of many anticancer drugs is the induction of apoptosis . Apoptosis is mediated through two distinct pathways: mitochondria‐dependent intrinsic apoptotic pathway and extrinsic apoptotic pathway.…”

Section: Introductionmentioning

confidence: 99%

Gold nanoparticles–conjugated quercetin induces apoptosis via inhibition of EGFR/PI3K/Akt–mediated pathway in breast cancer cell lines (MCF‐7 and MDA‐MB‐231)

Solaimuthu

Mukherjee

Das

et al. 2017

Cell Biochemistry & Function

141

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Epidermal growth factor plays a major role in breast cancer cell proliferation, survival, and metastasis. Quercetin, a bioactive flavonoid, is shown to exhibit anticarcinogenic effects against various cancers including breast cancer. Hence, the present study was designed to evaluate the effects of gold nanoparticles-conjugated quercetin (AuNPs-Qu-5) in MCF-7 and MDA-MB-231 breast cancer cell lines. Borohydride reduced AuNPs were synthesized and conjugated with quercetin to yield AuNPs-Qu-5. Both were thoroughly characterized by several physicochemical techniques, and their cytotoxic effects were assessed by MTT assay. Apoptotic studies such as DAPI, AO/EtBr dual staining, and annexin V-FITC staining were performed. AuNPs and AuNPs-Qu-5 were spherical with crystalline nature, and the size of particles range from 3.0 to 4.5 nm. AuNPs-Qu-5 exhibited lower IC value compared to free Qu. There was a considerable increase in apoptotic population with increased nuclear condensation seen upon treatment with AuNPs-Qu-5. To delineate the molecular mechanism behind its apoptotic role, we analysed the proteins involved in apoptosis and epidermal growth factor receptor (EGFR)-mediated PI3K/Akt/GSK-3β signalling by immunoblotting and immunocytochemistry. The pro-apoptotic proteins (Bax, Caspase-3) were found to be up regulated and anti-apoptotic protein (Bcl-2) was down regulated on treatment with AuNPs-Qu-5. Additionally, AuNPs-Qu-5 treatment inhibited the EGFR and its downstream signalling molecules PI3K/Akt/mTOR/GSK-3β. In conclusion, administration of AuNPs-Qu-5 in breast cancer cell lines curtails cell proliferation through induction of apoptosis and also suppresses EGFR signalling. AuNPs-Qu-5 is more potent than free quercetin in causing cancer cell death, and hence, this could be a potential drug delivery system in breast cancer therapy.

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Section: Introductionmentioning

confidence: 99%

Gold nanoparticles–conjugated quercetin induces apoptosis via inhibition of EGFR/PI3K/Akt–mediated pathway in breast cancer cell lines (MCF‐7 and MDA‐MB‐231)

Solaimuthu

Mukherjee

Das

et al. 2017

Cell Biochemistry & Function

141

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“…Commercially available formononetin 1 was subjected to etherification reaction with 1,2-dibromoethane, 1,3-dibromopropane, 1,4-dibromobutane, or 1,5-dibromopentane to afford 7a–d in the presence of potassium carbonate. The target analogues were easily obtained in high yields with the mature reaction conditions developed by our group [22]. …”

Section: Resultsmentioning

confidence: 99%

Design and synthesis of formononetin-dithiocarbamate hybrids that inhibit growth and migration of PC-3 cells via MAPK/Wnt signaling pathways

Zhang

Song

et al. 2017

European Journal of Medicinal Chemistry

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A series of novel formononetin-dithiocarbamate derivatives were designed, synthesized and evaluated for antiproliferative activity against three selected cancer cell line (MGC-803, EC-109, PC-3). The first structure-activity relationship (SAR) for this formononetin-dithiocarbamate scaffold is explored in this report with evaluation of 14 variants of the structural class. Among these analogues, tert-butyl 4-(((3-((3-(4-methoxyphenyl)-4-oxo-4H–chromen-7-yl)oxy)propyl)thio)carbonothioyl)piperazine-1-carboxylate (8i) showed the best inhibitory activity against PC-3 cells (IC50 = 1. 97 µM). Cellular mechanism studies elucidated 8i arrests cell cycle at G1 phase and regulates the expression of G1 checkpoint-related proteins in concentration-dependent manners. Furthermore, 8i could inhibit cell growth via MAPK signaling pathway and inhibit migration via Wnt pathway in PC-3 cells.

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“…Apoptosis is considered a major way that most of the anticancer drugs kill tumor cells [24]. Compound 11h was chosen to further explore its mechanism of action.…”

Section: Apoptosis Assaymentioning

confidence: 99%

Synthesis and anticancer activities of novel 1,2,4-triazolo[3,4-a]phthalazine derivatives

Xue

Zhang

Wang

et al. 2014

European Journal of Medicinal Chemistry

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Design, synthesis and antiproliferative activity studies of novel 1,2,3-triazole–dithiocarbamate–urea hybrids

Cited by 99 publications

References 56 publications

Gold nanoparticles–conjugated quercetin induces apoptosis via inhibition of EGFR/PI3K/Akt–mediated pathway in breast cancer cell lines (MCF‐7 and MDA‐MB‐231)

Gold nanoparticles–conjugated quercetin induces apoptosis via inhibition of EGFR/PI3K/Akt–mediated pathway in breast cancer cell lines (MCF‐7 and MDA‐MB‐231)

Design and synthesis of formononetin-dithiocarbamate hybrids that inhibit growth and migration of PC-3 cells via MAPK/Wnt signaling pathways

Synthesis and anticancer activities of novel 1,2,4-triazolo[3,4-a]phthalazine derivatives

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