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

被引:50
作者
de Oliveira, Ludmila G. [1 ]
Silva, Meiriane M. [1 ]
de Paula, Flavia C. S. [1 ]
Pereira-Maia, Elene C. [1 ]
Donnici, Claudio L. [1 ]
de Simone, Carlos A. [3 ]
Frezard, Frederic [4 ]
da Silva Junior, Eufranio N. [1 ,2 ]
Demicheli, Cynthia [1 ]
机构
[1] Univ Fed Minas Gerais, Dept Quim, Inst Ciencias Exatas, BR-31270901 Belo Horizonte, MG, Brazil
[2] Univ Fed Minas Gerais, Lab Quim Sintet & Heterocicl, BR-31270901 Belo Horizonte, MG, Brazil
[3] Univ Sao Paulo, Inst Fis, Dept Fis & Informat, BR-13560970 Sao Carlos, SP, Brazil
[4] Univ Fed Minas Gerais, Inst Ciencias Biol, Dept Fisiol & Biofis, BR-31270901 Belo Horizonte, MG, Brazil
关键词
antimony(V) complex; bismuth(V) complex; lapachol; cytotoxicity; cancer; IN-VITRO; DIPHENYLANTIMONY(III) DERIVATIVES; ORGANOBISMUTH COMPOUNDS; BETA-LAPACHONE; LIGANDS; ANALOGS; NAPHTHOQUINONES; PERSPECTIVES; CHEMISTRY; ONCOLOGY;
D O I
10.3390/molecules161210314
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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)(2)O. 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.
引用
收藏
页码:10314 / 10323
页数:10
相关论文
共 36 条
[1]   Triphenylarsenic(V) and -antimony(V) derivatives of multidentate Schiff bases: synthesis, characterization, and antimicrobial activities [J].
Agrawal, Reena ;
Sharma, Jyoti ;
Nandani, Durgesh ;
Batra, Amala ;
Singh, Yashpal .
JOURNAL OF COORDINATION CHEMISTRY, 2011, 64 (03) :554-563
[2]  
BARA A, 1991, ANTICANCER RES, V11, P1651
[3]   MANGANESE COMPLEXES WITH 2-HYDROXY-3(3-METHYL-2-BUTENYL)-1,4-NAPHTHOQUINONE (LAPACHOL) - REDOX CHEMISTRY AND SPECTROSCOPY IN DIMETHYLSULFOXIDE [J].
BODINI, ME ;
ARANCIBIA, V .
POLYHEDRON, 1989, 8 (11) :1407-1412
[4]   Novel coordination complexes in the bismuth(III)/oxinate system [J].
Campi, Eva M. ;
Deacon, Glen B. ;
Jackson, W. Roy ;
Skelton, Brian W. ;
Smith, Katherine A. ;
White, Allan H. .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 2006, 632 (8-9) :1483-1486
[5]   STRUCTURAL AND BIOLOGICAL CHARACTERIZATION OF ANTIMONY(V) POLYAMINES [J].
CARRAHER, CE ;
NAAS, MD ;
GIRON, DJ ;
CERUTIS, DR .
JOURNAL OF MACROMOLECULAR SCIENCE-CHEMISTRY, 1983, A19 (8-9) :1101-1120
[6]   Crystal and Molecular Structure of Manganese(II) Lapacholate, a Novel Polymeric Species Undergoing Temperature-Reversible Metal to Ligand Electron Transfer [J].
Caruso, Francesco ;
Martinez, Miguel A. ;
Rossi, Miriam ;
Goldberg, Alexander ;
Chacon Villalba, M. Elizabeth ;
Aymonino, Pedro J. .
INORGANIC CHEMISTRY, 2009, 48 (08) :3529-3534
[7]   3-Arylamino and 3-Alkoxy-nor-β-lapachone Derivatives: Synthesis and Cytotoxicity against Cancer Cell Lines [J].
da Silva, Eufranio N., Jr. ;
de Deus, Clara F. ;
Cavalcanti, Bruno C. ;
Pessoa, Claudia ;
Costa-Lotufo, Leticia V. ;
Montenegro, Raquel C. ;
de Moraes, Manoel O. ;
Pinto, Maria do Carmo F. R. ;
de Simone, Carlos A. ;
Ferreira, Vitor F. ;
Goulart, Marilia O. F. ;
Andrade, Carlos Kleber Z. ;
Pinto, Antonio V. .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (01) :504-508
[8]   The evaluation of quinonoid compounds against Trypanosoma cruzi: Synthesis of imidazolic anthraquinones, nor-β-lapachone derivatives and β-lapachone-based 1,2,3-triazoles [J].
da Silva Junior, Eufranio N. ;
Guimaraes, Tiago T. ;
Menna-Barreto, Rubem F. S. ;
Pinto, Maria do Carmo F. R. ;
de Simone, Carlos A. ;
Pessoa, Claudia ;
Cavalcanti, Bruno C. ;
Sabino, Jose R. ;
Andrade, Carlos Kleber Z. ;
Goulart, Marilia O. F. ;
de Castro, Solange L. ;
Pinto, Antonio V. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (09) :3224-3230
[9]   Antimalarial activity of phenazines from lapachol, β-lapachone and its derivatives against Plasmodium falciparum in vitro and Plasmodium berghei in vivo [J].
de Andrade-Neto, VF ;
Goulart, MOF ;
da Silva, JF ;
da Silva, MJ ;
Pinto, MD ;
Pinto, AV ;
Zalis, MG ;
Carvalho, LH ;
Krettli, AU .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (05) :1145-1149
[10]  
De Moura KCG, 2001, J BRAZIL CHEM SOC, V12, P325