Synthesis and Cytotoxicity of <i>N</i><sub>12</sub>-Ethyl Substituted Indolocarbazole Derivatives

马红光,; 王立平,; 徐志红,; 张亚鹏,; 李霞,; 朱伟明,

doi:10.6023/cjoc201602035

Cited by 4 publications

(3 citation statements)

References 12 publications

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“…BMA analogues were synthesized ( Figure 1A ) and their structures were unequivocally determined using NMR and MS as we previously described 15 . To synthesize compound 1 , 2-(1 H -indol-3-yl)acetic acid (3.5 g, 20 mmol) was added to a stirred suspension of NaH (4 g, 100 mmol, mixture of 60% NaH in mineral oil) in THF (80 mL) at 0°C.…”

Section: Methodsmentioning

confidence: 99%

Novel synthetic bisindolylmaleimide alkaloids inhibit STAT3 activation by binding to the SH2 domain and suppress breast xenograft tumor growth

Lin

Chen

et al. 2018

Oncogene

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Signal transducer and activator of transcription 3 (STAT3) is constitutively activated in malignant tumors and plays important roles in multiple aspects of cancer aggressiveness. Thus, targeting STAT3 promises to be an attractive strategy for treatment of advanced metastatic tumors. Bisindolylmaleimide alkaloid (BMA) has been shown to have anti-cancer activities and was thought to suppress tumor cell growth by inhibiting protein kinase C. In this study, we show that a newly synthesized BMA analogue, BMA097, is effective in suppressing tumor cell and xenograft growth and in inducing spontaneous apoptosis. We also provide evidence that BMA097 binds directly to the SH2 domain of STAT3 and inhibits STAT3 phosphorylation and activation, leading to reduced expression of STAT3 downstream target genes. Structure activity relationship analysis revealed that the hydroxymethyl group in the 2,5-dihydropyrrole-2,5-dione prohibits STAT3-inhibitory activity of BMA analogues. Together, we conclude that the synthetic BMA analogues may be developed as anticancer drugs by targeting and binding to the SH2 domain of STAT3 and inhibiting the STAT3 signaling pathway.

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Section: Methodsmentioning

confidence: 99%

Novel synthetic bisindolylmaleimide alkaloids inhibit STAT3 activation by binding to the SH2 domain and suppress breast xenograft tumor growth

Lin

Chen

et al. 2018

Oncogene

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“…采用细胞计数试剂盒-8 (CCK-8)测试化合物的肿瘤细胞增殖抑制活性 [26] . 用含体积分数为 10%的胎牛血清的 RPMI-1640 培养液将细胞配成单个细胞悬液(贴壁细胞和悬浮细胞的密度分别为 5×10 4…”

Section: 肿瘤细胞增殖抑制活性评价unclassified

Fermentation Optimization of the Caerulomycin H and the Synthesis of Cyanogriside K

Luo¹,

Gao²,

Yan³

et al. 2022

Chinese Journal of Organic Chemistry

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Caerulomycin H (2) and its 4-yl α-L-rhamnopyranoside [cyanogriside K (1)] are two microbial natural products from marine-derived Actinoalloteichus cyanogriseus WH1-2216-6. Cyanogriside K (1) shows good antiproliferative activity against tumor cells, whereas the yield is very low and the synthesis has not been reported. Thus, enough caerulomycin H (2) was first obtained by optimazing the fermentation condition of the mutant strain CRM05 of A. cyanogriseus WH1-2216-6. The yield of caerulomycin H (2) reached 272 mg/L (increased by 5 times) in the optimal solid medium consisted of corn pellets (80 g) and liqiud medium 5# for actinomycetes (100 mL). Then cyanogriside K (1) was synthesized with 25.6% total yield from caerulomycin H (2) by six steps reactions including deoximation, rhamnosylation, oximation and deacetylation. The structure of cyanogriside K (1) was identified by NMR, HRESIMS and specific rotation data. It is the same compound as the reported natural product. Furthermore, cyanogriside K (1) showed good bioactivity against the proliferation of the tumor cell lines PA-TU8988T, 786-O, 5673, DU145, A-375, FaDu and SF126, with the half maximal inhibitory concentration (IC50) values ranging from 1.07 μmol/L to 1.78 μmol/L.

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“…It has been reported that introducing a polar group containing a hydrogen bond donor could improve certain anticancer activity. 32 2.2.2 Induction of apoptosis. In recent years, many reports have indicated that various anticancer drugs or cancer chemopreventive agents, like DOX, can prevent tumor promotion and progression through inducing apoptosis.…”

Section: Biological Evaluationmentioning

confidence: 99%

Synthesis and potential antineoplastic activity of dehydroabietylamine imidazole derivatives

Zhao

et al. 2018

Med. Chem. Commun.

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Synthesis and Cytotoxicity of N₁₂-Ethyl Substituted Indolocarbazole Derivatives

Cited by 4 publications

References 12 publications

Novel synthetic bisindolylmaleimide alkaloids inhibit STAT3 activation by binding to the SH2 domain and suppress breast xenograft tumor growth

Novel synthetic bisindolylmaleimide alkaloids inhibit STAT3 activation by binding to the SH2 domain and suppress breast xenograft tumor growth

Fermentation Optimization of the Caerulomycin H and the Synthesis of Cyanogriside K

Synthesis and potential antineoplastic activity of dehydroabietylamine imidazole derivatives

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Synthesis and Cytotoxicity of N12-Ethyl Substituted Indolocarbazole Derivatives

Cited by 4 publications

References 12 publications

Novel synthetic bisindolylmaleimide alkaloids inhibit STAT3 activation by binding to the SH2 domain and suppress breast xenograft tumor growth

Novel synthetic bisindolylmaleimide alkaloids inhibit STAT3 activation by binding to the SH2 domain and suppress breast xenograft tumor growth

Fermentation Optimization of the Caerulomycin H and the Synthesis of Cyanogriside K

Synthesis and potential antineoplastic activity of dehydroabietylamine imidazole derivatives

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Synthesis and Cytotoxicity of N₁₂-Ethyl Substituted Indolocarbazole Derivatives