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Molecules 2011, 16(12), 10314-10323; doi:10.3390/molecules161210314

Antimony(V) and Bismuth(V) Complexes of Lapachol: Synthesis, Crystal Structure and Cytotoxic Activity

1
Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais (UFMG), Av. Antônio Carlos 6627, 31270-901 Belo Horizonte, MG, Brazil
2
Laboratório de Química Sintética e Heterocíclica, Universidade Federal de Minas Gerais (UFMG), 31270-901 Belo Horizonte, MG, Brazil
3
Departamento de Física e Informática, Instituto de Física, Universidade de São Paulo (USP), 13560-970 São Carlos, SP, Brazil
4
Departamento de Fisiologia e Biofísica, Instituto de Ciências Biológicas, Universidade Federal de Minas Gerais (UFMG), 31270-901 Belo Horizonte, MG, Brazil
*
Author to whom correspondence should be addressed.
Received: 3 November 2011 / Revised: 1 December 2011 / Accepted: 5 December 2011 / Published: 13 December 2011
(This article belongs to the Section Medicinal Chemistry)
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Abstract

Antimony(V) and bismuth(V) complexes of lapachol have been synthesized by the reaction of Ph3SbCl2 or Ph3BiCl2 with lapachol (Lp) and characterized by several physicochemical techniques such as IR, and NMR spectroscopy and X-ray crystallography. The compounds contain six-coordinated antimony and bismuth atoms. The antimony(V) complex is a monomeric derivative, (Lp)(Ph3Sb)OH, and the bismuth(V) complex is a dinuclear compound bridged by an oxygen atom, (Lp)2(Ph3Bi)2O. Both compounds inhibited the growth of a chronic myelogenous leukemia cell line and the complex of Bi(V) was about five times more active than free lapachol. This work provides a rare example of an organo-Bi(V) complex showing significant cytotoxic activity.
Keywords: antimony(V) complex; bismuth(V) complex; lapachol; cytotoxicity; cancer antimony(V) complex; bismuth(V) complex; lapachol; cytotoxicity; cancer
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Oliveira, L.G.; Silva, M.M.; Paula, F.C.S.; Pereira-Maia, E.C.; Donnici, C.L.; Simone, C.A.; Frézard, F.; Júnior, E.N.S.; Demicheli, C. Antimony(V) and Bismuth(V) Complexes of Lapachol: Synthesis, Crystal Structure and Cytotoxic Activity. Molecules 2011, 16, 10314-10323.

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