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Bioorg Med Chem ; 24(13): 2971-2978, 2016 07 01.
Article in English | MEDLINE | ID: mdl-27178387

ABSTRACT

The first series of nitric oxide donating derivatives of evodiamine were designed and prepared. NO releasing ability of all target derivatives was evaluated in BGC-823, Bel-7402 and L-02 cells. The cytotoxicity was evaluated against three human tumor cell lines (Bel-7402, A549 and BGC-823) and normal human liver cells L-02. The nitrate derivatives 11a and 11b only exhibited moderate activity and furoxan-based derivatives 13a-c, 14a and 14b showed promising activity. 13c showed good cytotoxic selectivity between tumor and normal liver cells and was further investigated for its apoptotic properties on human hepatocarcinoma Bel-7402 cells. The molecular mode of action revealed that 13c caused cell-cycle arrest at S phase and induced apoptosis in Bel-7402 cells through mitochondria-related caspase-dependent pathways.


Subject(s)
Antineoplastic Agents/pharmacology , Apoptosis/drug effects , Nitric Oxide/chemistry , Quinazolines/chemistry , Quinazolines/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/toxicity , Blotting, Western , Cell Cycle , Cell Line , Cell Line, Tumor , Cell Proliferation/drug effects , Cell Survival/drug effects , Humans , Inhibitory Concentration 50 , Molecular Structure , Quinazolines/toxicity
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