Anticancer activity and biophysical reactivity of copper complexes of 2-(benzo[d][1,3]dioxol-5-ylmethylene)-N-alkylhydrazinecarbothioamides

Authors

Floyd A. Beckford
Jeffrey Thessing
Alyssa Stott
Alvin A. Holder
Oleg G. Poluetov
Liya Li, University of Rhode Island
Navindra P. Seeram, University of Rhode IslandFollow

Document Type

Article

Date of Original Version

2012

Department

Biomedical and Pharmaceutical Sciences

Abstract

A series of copper complexes were synthesized from benzo[d][1,3]dioxole-5-carbaldehyde (piperonal) thiosemicarbazones (RHpTSC where R = H, CH3, C2H5 or C6H5 (Ph)). The complexes show interesting variations in geometry depending on the thiosemicarbazone; a dinuclear complex [Cu(HpTSC)Cl]2, a mononuclear complex [Cu(RHpTSC)2Cl2] (R = CH3 or C2H5) and another mononuclear complex [Cu(PhHpTSC)(PhpTSC)Cl] was generated. The complexes bind in a moderately strong fashion to DNA with binding constants on the order of 10⁴ M^{− 1}. They are also strong binders of human serum albumin with binding constants near 10⁴ M^{− 1}. The complexes show good in vitro cytotoxic profiles against two human colon cancer cell lines (HCT-116 and HT29) and two human breast cancer cell lines (MCF-7 and MDA-MB-231) with IC50 values in the low millimolar concentration range.

[Refer to PDF for graphical abstract]

Citation/Publisher Attribution

Beckford, F. A., Thessing, J., Slott, A., Holder, A. A., Poluektov, O. G., Li, L., & Seeram, N. P. (2012). Anticancer activity and biophysical reactivity of copper complexes of 2-(benzo[d][1,3]dioxol-5-ylmethylene)-N-alkylhydrazinecarbothioamides. Inorganic Chemistry Communications, 15, 225-229. doi: 10.1016/j.inoche.2011.10.032

Available at: https://doi.org/10.1016/j.inoche.2011.10.032

Creative Commons License

This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.