The biological in vitro effect and selectivity shown by a CoII complex of 2-(2-hydroxyphenylazo)-indole-3′-acetic acid on three distinctly different cancer cells

被引:2
作者
Ganguly, Durba [1 ]
Jain, Chetan Kumar [2 ,3 ]
Santra, Ramesh Chandra [1 ]
Roychoudhury, Susanta [2 ]
Majumder, Hemanta Kumar [3 ]
Das, Saurabh [1 ]
机构
[1] Jadavpur Univ, Dept Chem, Inorgan Sect, Kolkata 700032, India
[2] Indian Inst Chem Biol, Canc Biol & Inflammatory Disorder Div, Kolkata 700032, India
[3] Indian Inst Chem Biol, Infect Dis & Immunol Div, Kolkata 700032, India
关键词
CALF THYMUS DNA; AZO-DYE; METAL-COMPLEXES; 2-HYDROXYPHENYL-AZO-2'-NAPHTHOL HPAN; COPPER(II); ANTICANCER; REDUCTION; CHELATE; NICKEL(II); COBALT(II);
D O I
10.1039/c6ra23163b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A major intention of this study was to use the modified toxicity of the azo moiety in [2-(2-hydroxyphenylazo)-1H-indol-3-yl]-acetic acid (HPIA), achieved through complex formation with Co-II on some cancer cell lines. This is important because the azo functional group has not been tried in cancer chemotherapy. Keeping in mind aspects of drug resistance of some of the common anticancer drugs, a serious problem and a major clinical challenge in cancer chemotherapy, it is essential that new molecules are identified with anticancer activity. Although cytotoxicity of azo compounds is established there are not many reports that utilize them in cancer treatment. Another important aspect is to prepare compounds having preferential activity on cancer cells over normal cells so that toxic side effects are a minimum. Enzyme assay on the reductive cleavage of the azo bond showed complex formation with CoII almost completely checked the generation of cytotoxic amines implying that the complex could be less cytotoxic which was actually observed in case of normal healthy cells. Even though the complex formed less cytotoxic amines and possessed an almost similar binding ability with DNA like that of HPIA surprisingly its activity on three cancer cell lines namely human colon carcinoma HCT116 cells, acute lymphoblastic leukemia MOLT-4 cells and MCF-7 breast cancer cells was much greater than HPIA. The difference in activity between HPIA and its CoII complex on cancer cells showed no correlation with DNA binding or amine formation like that observed for normal cells. The complex probably possesses multiple modes of action whereby it is able to inhibit one or more cellular processes or functioning of different enzymes involved in the cell cycle of cancer cells for which it was found more effective.
引用
收藏
页码:114906 / 114915
页数:10
相关论文
共 62 条
[11]  
DANIEL J. W., 1962, TOXICOL AND APPL PHARMACOL, V4, P572, DOI 10.1016/0041-008X(62)90085-6
[12]   Synthesis, crystal structure, DNA interaction and in vitro anticancer activity of a Cu(II) complex of purpurin: dual poison for human DNA topoisomerase I and II [J].
Das, Piyal ;
Jain, Chetan Kumar ;
Dey, Sanjoy K. ;
Saha, Rajat ;
Chowdhury, Abhishek Dutta ;
Roychoudhury, Susanta ;
Kumar, Sanjay ;
Majumder, Hemanta Kumar ;
Das, Saurabh .
RSC ADVANCES, 2014, 4 (103) :59344-59357
[13]   Cyclic voltammetric studies of 1,2,4-trihydroxy-9,10-anthraquinone, its interaction with calf thymus DNA and anti-leukemic activity on MOLT-4 cell lines: a comparison with anthracycline anticancer drugs [J].
Das, Piyal ;
Guina, Partha Sarathi ;
Mandal, Parikshit C. ;
Paul, Mausumi ;
Paul, Santanu ;
Das, Saurabh .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2011, 24 (09) :774-785
[14]   Enhancement of anti-leukemic potential of 2-hydroxyphenyl-azo-2′-naphthol (HPAN) on MOLT-4 cells through conjugation with Cu(II) [J].
Deb, Tathagata ;
Gopal, Priya Kalyan ;
Ganguly, Durba ;
Das, Piyal ;
Paul, Mausumi ;
Saha, Manju Bikash ;
Paul, Santanu ;
Das, Saurabh .
RSC ADVANCES, 2014, 4 (35) :18419-18430
[15]   A complex of Co(II) with 2-hydroxyphenyl-azo-2′-naphthol (HPAN) is far less cytotoxic than the parent compound on A549-lung carcinoma and peripheral blood mononuclear cells: Reasons for reduction in cytotoxicity [J].
Deb, Tathagata ;
Choudhury, Diptiman ;
Guin, Partha Sarathi ;
Saha, Manju Bikash ;
Chakrabarti, Gopal ;
Das, Saurabh .
CHEMICO-BIOLOGICAL INTERACTIONS, 2011, 189 (03) :206-214
[16]   Synthesis, characterization, and biological activity of metal complexes of azohydrazone ligand [J].
El-Tabl, Abdou S. ;
Aly, Farag A. ;
Shakdofa, Mohamad M. E. ;
Shakdofa, Adel M. E. .
JOURNAL OF COORDINATION CHEMISTRY, 2010, 63 (04) :700-712
[17]   Azo pigments and a basal cell carcinoma at the thumb [J].
Engel, Eva ;
Ulrich, Heidi ;
Vasold, Rudolf ;
Koenig, Burkhard ;
Landthaler, Michael ;
Suettinger, Rudolf ;
Baeumler, Wolfgang .
DERMATOLOGY, 2008, 216 (01) :76-80
[18]   X-ray fluorescence microscopy reveals large-scale relocalization and extracellular translocation of cellular copper during angiogenesis [J].
Finney, Lydia ;
Mandava, Suneeta ;
Ursos, Lyann ;
Zhang, Wen ;
Rodi, Diane ;
Vogt, Stefan ;
Legnini, Daniel ;
Maser, Jorg ;
Ikpatt, Francis ;
Olopade, Olufunmilayo I. ;
Glesne, David .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (07) :2247-2252
[19]  
Forrest L., 2009, WO 2009097570 A2, Patent No. 2009097570
[20]  
Forrest L., 2009, PCT/US2009/032713, Patent No. 2009032713