Triphenylstannyl((arylimino)methyl)benzoates with selective potency that induce G1 and G2/M cell cycle arrest and trigger apoptosis via ROS in human cervical cancer cells

Metal complexes with organelle specificity and potent but selective cytotoxicity are highly desirable. A novel series of triphenylstannyl 4-((arylimino)methyl)benzoates (2-8) were obtained by the reactions of triphenylstannyl 4-formylbenzoate [Ph Sn(L )] 1 with primary aromatic amines. Two represent...

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Published in:Dalton transactions : an international journal of inorganic chemistry 2018, Vol.47 (6), p.1993-2008
Main Authors: Basu Baul, Tushar S, Longkumer, Imliwati, Duthie, Andrew, Singh, Priya, Koch, Biplob, Guedes da Silva, M Fátima C
Format: Article
Language:English
Subjects:
Amines
Aniline
Anticancer properties
Apoptosis
Aromatic compounds
Benzoates
Cancer
Cell cycle
Cell death
Cervical cancer
Coordination compounds
Cytometry
Cytotoxicity
Dyes
Flow cytometry
Infrared radiation
NMR spectroscopy
Nuclear reactions
Single crystals
Toxicity
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Summary:Metal complexes with organelle specificity and potent but selective cytotoxicity are highly desirable. A novel series of triphenylstannyl 4-((arylimino)methyl)benzoates (2-8) were obtained by the reactions of triphenylstannyl 4-formylbenzoate [Ph Sn(L )] 1 with primary aromatic amines. Two representative compounds (10, 11) were also synthesized by reacting aqua-triphenylstannyl 2-formylbenzoate [Ph Sn(L )(H O)] (9) with aniline and p-fluoroaniline, respectively. These compounds were characterized by elemental analysis, IR and H, C and Sn NMR spectroscopy, as well as single-crystal X-ray diffraction for compounds 5, 7-11 and three pro-ligands. The in vitro cytotoxic activities of 1-11 were assessed using the MTT tetrazolium dye assay against HeLa (human cervical) and MDA-MB-231 (breast) cancer cells, with IC values revealing high activity. Compared to cisplatin, compounds 1-11 exhibited enhanced cytotoxic efficacy, indicating their potential as potent anticancer agents. Among these, 1 and 5 demonstrated maximum inhibition in HeLa cells, with negligible effect on normal human embryonic kidney (HEK) cells. The combined results of the DCFH-DA dye and Hoechst 33342/PI nuclear staining assays, along with flow cytometry analysis, show that they possess a dual mode of action: They induced apoptotic cell death, attributable to the tin-assisted generation of reactive oxygen species. Cell cycle analyses indicated that compounds 1 and 5 exhibit cell growth inhibition and may cause turbulences in the G1 and G2/M phases.
ISSN:1477-9226
1477-9234
DOI:10.1039/c7dt04037g