Nuclear targeting and nuclear retention of anthracycline-formaldehyde conjugates implicates DNA covalent bonding in the cytotoxic mechanism of anthracyclines

Chemical Research in Toxicology

Volumn 12, Issue 7, 1999, Pages 588-596

  Taatjes, Dylan J ^b   Fenick, David J ^b   Koch, Tad H ^a  

^a UNIVERSITY OF COLORADO   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACYCLINE DERIVATIVE; DAUNOFORM; DAUNORUBICIN; DOXOFORM; DOXORUBICIN; EPIDOXOFORM; EPIRUBICIN; FORMALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; CANCER CELL CULTURE; COVALENT BOND; CYTOTOXICITY; DRUG DNA BINDING; FLUORESCENCE MICROSCOPY; HUMAN; HUMAN CELL; OXIDATIVE STRESS;

ALKYLATION; ANTINEOPLASTIC AGENTS; CELL NUCLEUS; DAUNORUBICIN; DNA, NEOPLASM; DOXORUBICIN; EPIRUBICIN; FORMALDEHYDE; HUMANS; RNA, NEOPLASM; SPECTROMETRY, FLUORESCENCE; TUMOR CELLS, CULTURED;

MINK CELL FOCUS-FORMING VIRUS;

EID: 0032817854     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx990008q     Document Type: Article

References (34)

1. Sweatman, T. W., and Israel, M. (1997) Anthracyclines. In Cancer Therapeutics, Experimental and Clinical Agents (Teicher, B. A., Ed.) pp 113-135, Humana Press, Totowa, NJ.
2. Tewey, K. M., Rowe, T. C., Yang, L., Halligan, B. D., and Liu, L. F. (1984) Adriamycin-induced DNA damage mediated by mammalian DNA topoisomerase II. Science 226, 466-468.
3. Pommier, Y. (1995) DNA topoisomerases and their inhibition by anthracyclines. In Anthracycline Antibiotics: New Analogues, Methods of Delivery, and Mechanisms of Action (Priebe, W., Ed.) pp 183-203, American Chemical Society, Washington, DC.
4. Chaires, J. B., Satyanarayana, S., Suh, D., Fokt, I., Przewloka, T., and Priebe, W. (1996) Parsing the free energy of anthracycline antibiotic binding to DNA. Biochemistry 35, 2047-2053.
5. Cullinane, C., Cutts, S. M., van Rosmalen, A., and Phillips, D. R. (1994) Formation of adriamycin-DNA adducts in vitro. Nucleic Acids Res. 22, 2296-2303.
6. Cullinane, C., van Rosmalen, A., and Phillips, D. R. (1994) Does adriamycin induce interstrand cross-links in DNA? Biochemistry 33, 4632-4638.
7. van Rosmalen, A., Cullinane, C., Cutts, S. M., and Phillips, D. R. (1995) Stability of adriamycin-induced DNA adducts and interstrand crosslinks. Nucleic Acids Res. 23, 42-50.
8. Taatjes, D. J., Gaudiano, G., Resing, K., and Koch, T. (1997) A redox pathway leading to the alkylation of DNA by the anthracycline, anti-tumor drugs, adrimaycin and daunomycin. J. Med. Chem. 40, 1276-1286.
9. Taatjes, D. J., Gaudiano, G., and Koch, T. H. (1997) Production of formaldehyde and DNA-adriamycin or -daunomycin adducts, initiated through redox chemistry of DTT/iron, xanthine oxidase/ NADH/iron, or glutathione/iron. Chem. Res. Toxicol. 10, 953-961.
10. Wang, A. H. J., Gao, Y. G., Liaw, Y. C., and Li, Y. k. (1991) Formaldehyde cross-links daunorubicin and DNA efficiently: HPLC and X-ray diffraction studies. Biochemistry 30, 3812-3815.
11. Taatjes, D. J., Fenick, D. J., and Koch, T. H. (1998) Epidoxoform: a hydrolytically more stable anthracycline-formaldehyde conjugate, cytotoxic to resistant tumor cells. J. Med. Chem. 41, 2452-2461.
12. Zeman, S. M., Phillips, D. R., and Crothers, D. M. (1998) Characterization of covalent Adriamycin-DNA adducts. Proc. Natl. Acad. Sci. U.S.A. 95, 11561-11565.
13. Skladanowski, A., and Konopa, J. (1993) Adriamycin and Daunomycin induce programmed cell death (apoptosis) in tumour cells. Biochem. Pharmacol. 46, 375-382.
14. Skladanowski, A., and Konopa, J. (1994) Relevance of interstrand DNA crosslinking induced by anthracyclines for their biological activity. Biochem. Pharmacol. 47, 2279-2287.
15. Skladanowski, A., and Konopa, J. (1994) Interstrand DNA crosslinking induced by anthracyclines in tumour cells. Biochem. Pharmacol. 47, 2269-2278.
16. Kartner, N., and Ling, V. (1989) Multidrug resistance in cancer. Sci. Am. 260, 44-51.
17. Gottesmann, M. M., and Pastam, I. (1993) Biochemistry of multidrug resistance mediated by the multidrug transporter. Annu. Rev. Biochem. 62, 385-427.
18. Sinha, B. K., and Mimnaugh, E. G. (1990) Free radicals and anticancer drug resistance: oxygen free radicals in the mechanisms of drug cytotoxicity and resistance by certain tumors. Free Radical Biol. Med. 8, 567-581.
19. Zwelling, L. A., Slovak, M. L., Doroshow, J, H., Hinds, M., Chan, D., Parker, E., Mayes, J., Sie, K. L., Meltzer, P. S., and Trent, J. M. (1990) HT1080/DR4: A P-glycoprotein-negative human fibrosarcoma cell line exhibiting resistance to topoisomerase II-reactive drugs despite the presence of a drug-sensitive topoisomerase II. J. Natl. Cancer Inst. 82, 1553-1561.
20. Cole, S. P. C., Downes, H. F., Mirski, S. E. L., and Clements, D. J. (1998) Alterations in glutathione and glutathione-related enzymes in a multidrug resistant small cell lung cancer cell line. Mol. Pharmacol. 37, 192-197.
21. Fairchild, C. R., Ivy, S. P., Kao-Shan, C. S., Whang-Peng, J., Rosen, N., Israel, M. A., Melera, P. W., Cowan, K. H., and Goldsmith, M. E. (1987) Isolation of amplified and overexpressed DNA sequences from adriamycin-resistant human breast cancer cells. Cancer Res. 47, 5141-5148.
22. Fenick, D. J., Taatjes, D. J., and Koch, T. H. (1997) Doxoform and Daunoform: anthracycline-formaldehyde conjugates toxic to resistant tumor cells. J. Med. Chem. 40, 2452-2461.
23. Durand, R. E., and Olive, P. L. (1981) Flow cytometry studies of intracellular adriamycin in single cells in vitro. Cancer Res. 41, 3489-3494.
24. Molinari, A., Cianfriglia, M., Meschini, S., Calcabrini, A., and Arancia, G. (1994) P-Glycoprotein expression in the golgi apparatus of multidrug-resistant cells. Int. J. Cancer 59, 789-795.
25. Leng, F., Savkur, R., Fokt, I., Przewloka, T., Priebe, W., and Chaires, J. B. (1996) Base specific and regiospecific chemical cross-linking of Daunorubicin to DNA. J. Am. Chem. Soc. 118, 4731-4738.
26. Gallois, L., Fiallo, M., Laigle, A., Priebe, W., and Garnier-Sullerot, A. (1996) The overall partitioning of anthracyclines into phosphatidyl-containing model membranes depends neither on the drug charge nor the presence of anionic phospholipids. Eur. J. Biochem. 241, 879-887.
27. Crooke, S. T., and DuVernay, V. H. (1980) Fluorescence quenching of anthracyclines by subcellular fractions. In Anthracyclines Current Status and New Developments (Crooke, S. T., and Reich, S. D., Eds.) pp 151-155, Academic Press, New York.
28. Roche, C. J., Thomson, J. A., and Crothers, D. M. (1994) Site selectivity of daunomycin. Biochemistry 33, 926-935.
29. Gervasoni, J. E., Jr., Fields, S. Z., Krishna, S., Baker, M. A., Rosado, M., Thuraisamy, K., Hindenburg, A. A., and Taub, R. N. (1991) Subcellular distribution of daunorubicin in P-glycoprotein-positive and -negative drug-resistant cell lines using laser-assisted confocal microscopy. Cancer Res. 51, 4955-4963.
30. Coley, H. M., Amos, W. B., Twintyman, P. R., and Workman, P. (1993) Examination by laser confocal fluorescence imaging microscopy of the subcellular localisation of anthracyclines in parent and multidrug resistant cell lines. Br. J. Cancer 67, 1316-1323.
31. Serafino, A., Sinibaldi-Vallebona, P., Gaudiano, G., Koch, T. H., Rasi, G., Garaci, E., and Ravagnan, G. (1998) Cytoplasmic localization of anthracycline antitumor drugs conjugated with reduced glutathione: a possible correlation with multidrug resistance. Anticancer Res. 18, 1159-1166.
32. Mimnaugh, E. G., Fairchild, C. R., Fruehauf, J. P., and Sinha, B. K. (1991) Biochemical and pharmacological characterization of MCF-7 drug-sensitive and Adr multidrug-resistant human breast tumor xenografts in athymic nude mice. Biochem. Pharmacol. 42, 391-402.
33. a values of amino sugars. Chem. Pharm. Bull. 16, 1134-1137.
34. Lampidis, T. J., Kolonias, D., Podona, T., Israel, M., Safa, A. R., Lothstein, L., Savaraj, N., Tapiero, H., and Priebe, W. (1997) Circumvention of P-GP MDR as a function of anthracycline lipophilicity and charge. Biochemistry 36, 2679-2685.