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Issue 124, 2015
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Study of the effect of molecular structure and alkyl groups bound with tin(IV) on their cytotoxicity of organotin(IV) 2-phenyl-4-selenazole carboxylates

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Abstract

Five organotin(IV) compounds Ph3SnL (1), (R2Sn)4O2L4 [R = n-Bu (2), n-Oct (3)], (R2Sn)4O2L2Cl2 [R = n-Bu (4), Me (5)], have been synthesized from the reactions of 2-phenyl-4-selenazole carboxylic acid (HL) with the corresponding organotin(IV) oxide or chlorides. These compounds have been characterized by elemental analysis, IR, 1H, 13C and 119Sn NMR spectroscopy, and single crystal X-ray diffraction analysis. Structural studies reveal that compound 1 exhibits a mononuclear four-coordinated tetrahedral geometry. Differently, the crystal structures of compounds 2–5 reveal the formation of the tetranuclear species containing a planar Sn4O4 core. All compounds were screened for their in vitro cytotoxic activities toward three cancer cell lines (Caco-2, A549, and HCT-116) and one normal rat hepatocyte cell line (BRL). The results indicate that both di-n-butyltin(IV) and triphenyltin(IV) derivatives not only show excellent cytotoxic activities on cisplatin-sensitive lung cancer cell line A549 and but also exhibit good cytotoxicity against cisplatin-insensitive colon cancer cell lines HCT-116 and Caco-2. Whereas, dimethyltin(IV) and di-n-octyltin(IV) complexes exhibit lower or no cytotoxic activity. The structure–activity relationship of the cytotoxicity of the title complexes has also been discussed.

Graphical abstract: Study of the effect of molecular structure and alkyl groups bound with tin(iv) on their cytotoxicity of organotin(iv) 2-phenyl-4-selenazole carboxylates

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Publication details

The article was received on 11 Sep 2015, accepted on 18 Nov 2015 and first published on 27 Nov 2015


Article type: Paper
DOI: 10.1039/C5RA18445B
Citation: RSC Adv., 2015,5, 102885-102894
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    Study of the effect of molecular structure and alkyl groups bound with tin(IV) on their cytotoxicity of organotin(IV) 2-phenyl-4-selenazole carboxylates

    M. Hong, Y. Yang, C. Li, L. Xu, D. Li and C. Li, RSC Adv., 2015, 5, 102885
    DOI: 10.1039/C5RA18445B

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