Detection of Labile Anthracycline-DNA Adducts by Real-Time PCR

Oncology Research

Volumn 13, Issue 11, 2002, Pages 479-489

  Spencer, Damian M S ^a   Cutts, Suzanne M ^a   Kimura, Ken Ichi ^b   Gray, Peter J ^c   Phillips, Don R ^a  

^a LA TROBE UNIVERSITY   (Australia)

^b IWATE UNIVERSITY   (Japan)

^c DEFENCE SCIENCE AND TECHNOLOGY ORGANISATION   (Australia)

Author keywords

Anthracyclines; Barminomycin; DNA adducts; Doxorubicin; Real time PCR

Indexed keywords

ANTHRACYCLINE ANTIBIOTIC AGENT; BARMINOMYCIN I; DOXORUBICIN;

ANALYTIC METHOD; ARTICLE; BASE PAIRING; CELL FREE SYSTEM; COVALENT BOND; CROSS LINKING; DNA ADDUCT; DNA DENATURATION; DNA DRUG COMPLEX; DRUG DETERMINATION; EARLY DIAGNOSIS; PRIORITY JOURNAL; REAL TIME POLYMERASE CHAIN REACTION; THERMOSTABILITY;

EID: 0842348976     PISSN: 09650407     EISSN: None     Source Type: Journal    
DOI: 10.3727/000000003108748009     Document Type: Article

References (38)

1. Myers, C, E.; Minnaugh, E, G.; Yeh, G. C.; Sinha, B. K. Biochemical mechanisms of tumor cell kill by the anthracyclines. In: Lown, J. W., eds, Anthracycline and anthracenedione-based anticancer agents. Amsterdam: Elsevier Science Publishers; 1988:527-570.
2. Hortobagyi, G. N. Anthracyclines in the treatment of cancer. An overview. Drugs 54(Suppl. 4):1-7; 1997.
3. Cutts, S. M.; Phillips, D. R. Use of oligonucleotides to define the site of interstrand cross-links induced by adriamycin. Nucleic Acids Res. 23:2450-2456; 1995,
4. Leng, F. F.; Savkur, R.; Fokt, I.; Przewloka, T.; Priebe, W.; Chaires, J. B. Base specific and regioselective chemical cross-linking of daunorubicin to DNA. J. Am. Chem. Soc. 118:4731-4738; 1996.
5. Wang, A. H.; Gao, Y. G.; Liaw, Y. C.; Li, Y. K. Formal-dehyde cross-links daunorubicin and DNA efficiently: HPLC and X-ray diffraction studies. Biochemistry 30: 3812-3815; 1991.
6. Zeman, S. M.; Phillips, D. R.; Crothers, D. M. Characterization of covalent adriamycin-DNA adducts. Proc. Natl. Acad. Sci. USA 95:11561-11565; 1998.
7. Taatjes, D. J.; Gaudiano, G.; Koch, T. H. Production of formaldehyde and DNA-adriamycin or DNA-daunomycin adducts, initiated through redox chemistry of dithiothreitol/iron, xanthine oxidase/NADH/iron, or glutathione/iron, Chem. Res. Toxicol. 10:953-961; 1997.
8. van Rosmalen, A.; Cullinane, C.; Cutts, S, M.; Phillips, D. R. Stability of adriamycin-induced DNA adducts and interstrand crosslinks, Nucleic Acids Res. 23:42-50; 1995.
9. Skladanowski, A.; Konopa, J. Relevance of interstrand DNA crosslinking induced by anthracyclines for their biological activity. Biochem. Pharmacol. 47:2279-2287; 1994.
10. Cutts, S. M.; Rephaeli, A.; Nudelman, A.; Hmelnitsky, I.; Phillips, D. R. Molecular basis for the synergistic interaction of adriamycin with the formaldehyde-releasing pro-drug pivaloyloxymethyl butyrate (AN-9). Cancer Res. 61: 8194-8202; 2001.
11. Kimura, K.; Nakayama, S.; Koyama, T.; Shimada, S.; Kawaguchi, N.; Miyata, N.; Takeshita, Y.; Kawanishi, G. SN-07 chromophore: An anthracycline antibiotic from the macromolecular antibiotic SN-07. J. Antibiot. (Tokyo) 40: 1353-1355; 1987.
12. Kimura, K.; Nakayama, S.; Miyata, N.; Takeshita, Y.; Kawanishi, G. The structure of SN-07 chromophore. J. Antibiot. (Tokyo) 41:411-414; 1988.
13. Uchida, T.; Imoto, M.; Takahashi, Y.; Odagawa, A.; Sawa, T.; Tatsuta, K. ; Naganawa, H.; Hamada, M.; Takeuchi, T.; Umezawa, H. New potent anthracyclines, barminomycins I and II, J. Antibiot. (Tokyo) 41:404-408; 1988.
14. Moufarij, M. A.; Cutts, S. M.; Neumann, G. M.; Kimura, K.; Phillips, D. R. Barminomycin functions as a potent pre-activated analogue of adriamycin. Chem. Biol. Interact. 138:137-153; 2001.
15. Perrin, L. C.; Cullinane, C.; Kimura, K.; Phillips, D. R. Barminomycin forms gc-specific adducts and virtual interstrand crosslinks with DNA. Nucleic Acids Res. 27:1781-1787; 1999.
16. Hartley, J. A.; Souhami, R. L.; Berardini, M. D. Electrophoretic and chromatographic separation methods used to reveal interstrand crosslinking of nucleic acids. J. Chromatogr. 618:277-288; 1993.
17. Hartley, J. A.; Berardini, M. D.; Souhami, R. L. An agarose gel method for the determination of DNA interstrand crosslinking applicable to the measurement of the rate of total and "second-arm" crosslink reactions. Anal. Biochem. 193:131-134; 1991.
18. Morgan, A. R.; Lee, J. S.; Pulleyblank, D. E.; Murray, N. L.; Evans, D. H. Review: Ethidium fluorescence assays. Part 1. Physicochemical studies. Nucleic Acids Res. 7:547-569; 1979.
19. Vos, J. M.; Hanawalt, P. C. Processing of psoralen adducts in an active human gene: Repair and replication of DNA containing monoadducts and interstrand cross-links. Cell 50:789-799; 1987.
20. Lin, P. F.; Bardwell, E.; Howard-Flanders, P. Initiation of genetic exchanges in lambda phage-prophage crosses. Proc. Natl. Acad. Sci. USA 74:291-295; 1977.
21. Borowy-Borowski, H.; Lipman, R.; Chowdary, D.; Tomasz, M. Duplex oligodeoxyribonucleotides cross-linked by mitomycin C at a single site: Synthesis, properties, and cross-link reversibility. Biochemistry 29:2992-2999; 1990.
22. Kohn, K. W.; Erickson, L. C.; Ewig, R. A.; Friedman, C. A. Fractionation of DNA from mammalian cells by alkaline elution, Biochemistry 15:4629-4637; 1976.
23. Verly, W. G.; Brakier, L. The lethal action of monofunctional and bifunctional alkylating agents on T7 coliphage. Biochim. Biophys. Acta 174:674-685; 1969.
24. Fujiwara, Y. Measurement of interstrand cross-links produced by mitomycin C. In: Friedberg, E. C.; Hanawalt, P. C., eds. DNA repair: A laboratory manual of research procedures. New York: Marcel Dekker; 1983:143-160.
25. Tomasz, M.; Mercado, C. M.; Olson, J.; Chatterjie, N. The mode of interaction of mitomycin C with deoxyribonucleic acid and other polynucleotides in vitro. Biochemistry 13:4878-4887; 1974.
26. Cullinane, C.; Cutts, S. M.; Panousis, C.; Phillips, D. R. Interstrand cross-linking by adriamycin in nuclear and mitochondrial DNA of MCF-7 cells. Nucleic Acids Res. 28: 1019-1025; 2000.
27. Capranico, G.; Soranzo, C.; Zunino, F. Single-strand DNA breaks induced by chromophore-modified anthracyclines in P388 leukemia cells. Cancer Res. 46:5499-5503; 1986.
28. Yajima, N.; Hochi, S.; Miyata, N.; Kishi, T.; Kawanishi, G. DNA breaks and repair in the mouse leukemia L1210 cells exposed to three different types of interstrand DNA cross-linkers. Mutat. Res. 236:43-50; 1990.
29. Grimaldi, K. A.; Bingham, J. P.; Souhami, R. L.; Hartley, J. A. DNA damage by anticancer agents and its repair: Mapping in cells at the subgene level with quantitative polymerase chain reaction. Anal. Biochem. 222:236-242; 1994.
30. Jennerwein, M. M.; Eastman, A. A polymerase chain reaction-based method to detect cisplatin adducts in specific genes. Nucleic Acids Res. 19:6209-6214; 1991.
31. Kalinowski, D. P.; Illenye, S.; Van Houten, B. Analysis of DNA damage and repair in murine leukemia L1210 cells using a quantitative polymerase chain reaction assay. Nucleic Acids Res. 20:3485-3494; 1992.
32. Vos, J. M. Analysis of psoralen monoadducts and interstrand crosslinks in defined genomic sequences. In: Friedberg, E. C.; Hanawalt, P. C., eds. DNA repair: A laboratory manual of research procedures. New York: Marcel Dekker; 1988:367-398.
33. Ye, X.; Kimura, K.; Patel, D. J. Site-specific intercalation of an anthracycline antitumor antibiotic into a Y-RY triplex through covalent adduct formation. J. Am. Chem. Soc. 115:9325-9326; 1993.
34. Cutts, S. M.; Parker, B. S.; Swift, L. P.; Kimura, K. I.; Phillips, D. R. Structural requirements for the formation of anthracycline-DNA adducts. Anticancer Drug Des. 15: 373-386; 2000.
35. Talarico, T.; Cullinane, C. M.; Gray, P. J.; Webster, L. K.; Deacon, G. B.; Phillips, D. R. Nuclear and mitochondrial distribution of organoamidoplatinum(II) lesions in cisplatin-sensitive and -resistant adenocarcinoma cells. Anticancer Drug Des. 16:135-141; 2001.
36. Varadaraj, K.; Skinner, D. M. Denaturants or cosolvents improve the specificity of PCR amplification of a G + C-rich DNA using genetically engineered DNA polymerases. Gene 140:1-5; 1994.
37. Pomp, D.; Medrano, J. F. Organic solvents as facilitators of polymerase chain reaction. Biotechniques 10:58-59; 1991.
38. Lee, C. H.; Mizusawa, H.; Kakefuda, T. Unwinding of double-stranded DNA helix by dehydration. Proc. Natl. Acad. Sci. USA 78:2838-2842; 1981.