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

被引:28
作者
Beckford, Floyd A. [1 ]
Thessing, Jeffrey [1 ]
Stott, Alyssa [1 ]
Holder, Alvin A. [2 ]
Poluektov, Oleg G. [3 ]
Li, Liya [4 ]
Seeram, Navindra P. [4 ]
机构
[1] Lyon Coll, Div Sci, Batesville, AR 72501 USA
[2] Univ So Mississippi, Dept Chem & Biochem, Hattiesburg, MS 39406 USA
[3] Argonne Natl Lab, Chem Sci & Engn Div, Argonne, IL 60439 USA
[4] Univ Rhode Isl, Bioact Bot Res Lab, Dept Biomed & Pharmaceut Sci, Kingston, RI 02881 USA
基金
美国国家科学基金会;
关键词
Human serum albumin; Thiosemicarbazones; Anticancer; DNA binding; Structural variation; TRANSITION-METAL-COMPLEXES; DNA-BINDING; THIOSEMICARBAZONE COMPLEXES; AGENTS;
D O I
10.1016/j.inoche.2011.10.032
中图分类号
O61 [无机化学];
学科分类号
070301 [无机化学];
摘要
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 10(4)M(-1). They are also strong binders of human serum albumin with binding constants near 10(4) M-1. The complexes show good in vitro cytotoxic profiles against two human colon cancer cell lines (HT-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. (C) 2011 Elsevier B.V. All rights reserved.
引用
收藏
页码:225 / 229
页数:5
相关论文
共 27 条
[1]
Transition metal complexes of phenanthrenequinone thiosemicarbazone as potential anticancer agents: synthesis, structure, spectroscopy, electrochemistry and in vitro anticancer activity against human breast cancer cell-line, T47D [J].
Afrasiabi, Z ;
Sinn, E ;
Padhye, S ;
Dutta, S ;
Padhye, S ;
Newton, C ;
Anson, CE ;
Powell, AK .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2003, 95 (04) :306-314
[2]
UBER EMPROTIDE SCHWERMETALL-INNERKOMPLEXE DER ALPHA-DIKETONDITHIOSEMICARBAZONE (THIAZONE).3. [J].
BAHR, G ;
SCHLEITZER, E .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1955, 278 (3-4) :136-154
[3]
UBER EMPROTIDE SCHWERMETALL-INNERKOMPLEXE DER ALPHA-DIKETONDITHIOSEMICARBAZONE (THIAZONE) .2. [J].
BAHR, G .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1953, 273 (06) :325-332
[4]
UBER EMPROTIDE SCHWERMETALL-INNERKOMPLEXE DER ALPHA-DIKETONDITHIOSEMICARBAZONE (THIAZONE) .1. [J].
BAHR, G .
ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1952, 268 (4-6) :351-363
[5]
Half-sandwich ruthenium-arene complexes with thiosemicarbazones: Synthesis and biological evaluation of [(η6-p-cymene)Ru(piperonal thiosemicarbazones)Cl]Cl complexes [J].
Beckford, Floyd ;
Dourth, Deidra ;
Shaloski, Michael, Jr. ;
Didion, Jacob ;
Thessing, Jeffrey ;
Woods, Jason ;
Crowell, Vernon ;
Gerasimchuk, Nikolay ;
Gonzalez-Sarrias, Antonio ;
Seeram, Navindra P. .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2011, 105 (08) :1019-1029
[6]
Synthesis and characterization of mixed-ligand diimine-piperonal thiosemicarbazone complexes of ruthenium(II): Biophysical investigations and biological evaluation as anticancer and antibacterial agents [J].
Beckford, Floyd A. ;
Thessing, Jeffrey ;
Shaloski, Michael, Jr. ;
Mbarushimana, P. Canisius ;
Brock, Alyssa ;
Didion, Jacob ;
Woods, Jason ;
Gonzalez-Sarrias, Antonio ;
Seeram, Navindra P. .
JOURNAL OF MOLECULAR STRUCTURE, 2011, 992 (1-3) :39-47
[7]
OXIDATIVE STRESS-INDUCED BY A COPPER THIOSEMICARBAZONE COMPLEX [J].
BYRNES, RW ;
MOHAN, M ;
ANTHOLINE, WE ;
XU, RX ;
PETERING, DH .
BIOCHEMISTRY, 1990, 29 (30) :7046-7053
[8]
Transition metal quinone-thiosemicarbazone complexes 1: Evaluation of EPR covalency parameters and redox properties of pseudo-square-planar copper(II)-naphthoquinone thiosemicarbazones [J].
Chikate, RC ;
Belapure, AR ;
Padhye, SB ;
West, DX .
POLYHEDRON, 2005, 24 (08) :889-899
[9]
Eftnik R., 1981, ANAL BIOCHEM, V44, P199