Induction of apoptosis in human cancer cell lines by diospyrin, a plant-derived bisnaphthoquinonoid, and its synthetic derivatives

Cancer Letters

Volumn 188, Issue 1-2, 2002, Pages 85-93

  Chakrabarty, Sutapa ^a   Roy, Madhumita ^a   Hazra, Banasri ^b   Bhattacharya, R K ^a  

^a CHITTARANJAN NATIONAL CANCER INSTITUTE   (India)

^b JADAVPUR UNIVERSITY   (India)

Author keywords

Apoptosis; Bisnaphthoquinonoid; Caspase activity; Diospyrin; DNA fragmentation; Tumor cells

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; 3 (4,5 DIMETHYL 2 THIAZOLYL) 2,5 DIPHENYLTETRAZOLIUM BROMIDE; CASPASE 3; CASPASE 8; DIOSPYRIN; DNA; DNA FRAGMENT; GENOMIC DNA; PROPIDIUM IODIDE; TRYPAN BLUE;

ACUTE MYELOBLASTIC LEUKEMIA; APOPTOSIS; ARTICLE; BREAST ADENOCARCINOMA; CANCER CELL CULTURE; CELL GROWTH; CELL STRAIN HL 60; CELL STRAIN K 562; CELL STRAIN MCF 7; CHROMATIN CONDENSATION; CHRONIC MYELOID LEUKEMIA; CONTROLLED STUDY; CULTURE MEDIUM; CYTOTOXICITY; DNA SYNTHESIS; DRUG EFFICACY; DRUG MECHANISM; ENZYME ACTIVATION; FLUORESCENCE ANALYSIS; GEL ELECTROPHORESIS; HELA CELL; HUMAN; HUMAN CELL; LYMPHOCYTE; MICROSCOPY; PRIORITY JOURNAL; UTERINE CERVIX CARCINOMA;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CASPASE 3; CASPASE 8; CASPASE 9; CASPASES; CELL DIVISION; DIOSPYROS; HUMANS; MICROSCOPY, FLUORESCENCE; NAPHTHOQUINONES; NEOPLASMS; PLANT BARK; TUMOR CELLS, CULTURED;

EID: 0037114352     PISSN: 03043835     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0304-3835(02)00494-9     Document Type: Article

References (35)

1. O'Brien P.J. Molecular mechanisms of quinone cytotoxicity. Chem.-Biol. Interact. 80:1991;1-41.
2. Powis G. Metabolism and reactions of quinonoid anticancer agents. Pharmacol. Ther. 35:1987;157-162.
3. Li C.J., Wang C., Pardee A.B. Induction of apoptosis by β-lapachone in human prostate cancer cells. Cancer Res. 55:1995;3712-3715.
4. Muller I., Jenner A., Bruchelt G., Niethammer D., Halliwell B. Effect of concentration on the cytotoxic mechanism of doxorubicin - Apoptosis and oxidative DNA damage. Biochem. Biophys. Res. Commun. 230:1997;254-257.
5. Hueber A., Esser P., Heimann K., Kocik N., Winter S., Weller M. The topoisomerase I inhibitors, camptothecin and β-lapachone, induce apoptosis of retinal pigment epithelial cells. Exp. Eye Res. 67:1998;525-530.
6. Yoon Y., Kim Y.O., Lim N.Y., Jeon W.K., Sung H.J. Shikonin, an ingredient of Lithospermum erythrorhizon induced apoptosis in HL-60 human promyelocytic leukemia cell line. Planta Med. 65:1999;532-535.
7. Huang L., Pardee A.B. β-Lapachone induces cell cycle arrest and apoptosis in human colon cancer cells. Mol. Med. 5:1999;711-720.
8. Pan J., Simamura E., Koyama J., Shimada H., Hirai K.I. Induced apoptosis and necrosis by 2-methylfuranonaphthoquinone in human cervical cancer HeLa cells. Cancer Detect. Prev. 24:2000;266-274.
9. Li Y., Li C.J., Yu D., Pardee A.B. Potent induction of apoptosis by β-lapachone in human multiple myeloma cell lines and patient cells. Mol. Med. 6:2000;1008-1015.
10. Planchon S.M., Pink J.J., Tagliarino C., Bornman W.G., Varnes M.E., Boothman D.A. β-Lapachone-induced apoptosis in human prostate cancer cells: involvement of NQO1/xip3. Exp. Cell Res. 267:2001;95-106.
11. Hazra B., Sur P., Banerjee A., Roy D.K. A preliminary note on the activity of Diospyros montana bark extract on Ehrlich ascites carcinoma in mice. J. Ind. Chem. Soc. 58:1981;627-628.
12. Hazra B., Sur P., Roy D.K., Sur B., Banerjee A. Biological activity of diospyrin towards Ehrlich ascites carcinoma in Swiss A mice. Planta Med. 51:1984;295-297.
13. Hazra B., Pal S., Banerjee A. New diospyrin derivatives with tumor inhibitory activity towards Ehrlich ascites carcinoma. Med. Sci. Res. 22:1994;351-353.
14. Hazra B., Pal S., Banerjee A., Ray R., Bhattacharya D.K. Pharmacological studies on the effect of the treatment of Swiss A mice with diospyrin, a tumor inhibitory plant product and its synthetic derivatives. Phytother. Res. 10:1996;393-397.
15. Bollum F.J. Filter paper disc technique for assaying radioactive macromolecules. Methods Enzymol. 12B:1968;169-173.
16. Hermann H., Lorenz H.-M., Voll R., Grunke M., Woith W., Kalden J.R. A rapid and simple method for the isolation of apoptotic DNA fragments. Nucleic Acids Res. 22:1994;5506-5507.
17. Compton M.M. A biochemical hallmark of apoptosis: internucleosomal degradation of the genome. Cancer Metastasis Rev. 11:1992;105-109.
18. Hazra B., Ghosh R., Banerjee A., Kirby G.C., Warhurst D.C., Phillipson J.D. In vitro antiplasmodial effects of diospyrin, a plant-derived naphthoquinonoid, and a novel series of derivatives. Phytother. Res. 9:1995;72-74.
19. Yardley V., Snowdon D., Croft S., Hazra B. In vitro activity of diospyrin and derivatives against Leishmania donovani, Trypanosoma cruzi and Trypanosoma brucei. Phytother. Res. 10:1996;559-562.
20. Kovacic P., Ames J.R., Grogan J.W., Hazra B., Ryan M.D. Anticancer quinones and quinolines: mode of action via electron transfer and oxidative stress. Dryhurst G., Niki K., Redox Chemistry and Interfacial Behaviour of Biological Molecules. 1988;295-307 Plenum Press, New York.
21. Dickancaite E., Cenas N., Kalvelyte A., Serapiniene N. Toxicity of daunorubicin and naphthoquinones to HL-60 cells: an involvement of oxidative stress. Biochem. Mol. Biol. Int. 41:1997;987-989.
22. Laux I., Nel A. Evidence that oxidative stress-induced apoptosis by menadione involves Fas-dependent and Fas-independent pathways. Clin. Immunol. 101:2001;335-344.
23. Dubin M., Fernandez S.H.V., Stoppani A.O. Cytotoxicity of β-lapachone, a naphthoquinone with possible therapeutic use. Medicina (B Aires). 61:2001;343-350.
24. Ray S., Hazra B., Mittra B., Dads A., Majumdar H.K. Diospyrin, a bisnaphthoquinone: a novel inhibitor of type I DNA topoisomerase of Leishmania donovani. Mol. Pharmacol. 54:1998;994-999.
25. Ahn B.-Z., Baik K.-U., Kweon G.-R., Hwang B.-D. Acylshikonin analogues: synthesis and inhibition of DNA topoisomerase. J. Med. Chem. 38:1995;1044-1047.
26. Frydman B., Marton L.J., Sun J.S., Neder K., Witiak D.T., Liu A.A., Wang H.-M., Mao Y., Wu H.-Y., Sanders M.M., Liu L.F. Induction of DNA topoisomerase mediated DNA cleavage by β-lapachone and related naphthoquinones. Cancer Res. 57:1997;620-627.
27. Oren M. The involvement of oncogenes and tumor suppressor genes in the control of apoptosis. Cancer Metastasis Rev. 11:1992;141-148.
28. Reed J.C. Bcl-2 and the regulation of programmed cell death. J. Cell Biol. 124:1994;1-6.
29. Dolan M.E., Freidman B., Thompson C.B., Diamond A.M., Garbiras B.J., Safa A.R., Beck W.T., Marton L.J. Effects of 1,2-naphthoquinones on human tumor cell growth and lack of cross-resistance with other anticancer agents. Anticancer Drugs. 9:1998;437-448.
30. Thornberry N.A. The caspase family of cysteine proteases. Br. Med. Bull. 53:1997;478-490.
31. Thornberry N.A. Caspases: key mediators of apoptosis. Chem. Biol. 5:1998;R97-R103.
32. Nicholson D.W., Thornberry N.A. Caspases: killer proteases. Trends Biochem. Sci. 22:1997;299-306.
33. Thornberry N.A., Lazebnick Y. Caspases: enemies within. Science. 281:1998;1312-1316.
34. Don M.J., Chang Y.H., Chen K.K., Ho L.K., Chau Y.P. Induction of CDK inhibitors (p21(WAF1) and p27(Kip1)) and Bak in the β-lapachone-induced apoptosis of human prostate cancer cells. Mol. Pharmacol. 59:2001;784-794.
35. 2 terminus potentiates naphthaquinone analog-induced apoptosis. J. Biol. Chem. 276:2001;24538-24644.