Sequence specificity and reactivity of the binding of phenazine-tethered platinum complexes to DNA

Anti-Cancer Drug Design

Volumn 14, Issue 3, 1999, Pages 243-252

  Perrin, Leah C ^a   Cullinane, Carleen ^b   McFadyen, W David ^a   Phillips, Don R ^b  

^a UNIVERSITY OF MELBOURNE   (Australia)

^b LA TROBE UNIVERSITY   (Australia)

Author keywords

Cisplatin; DNA binding; DNA platination; Kinetics; Phenazine tethered platinum

Indexed keywords

LIGAND; NUCLEOTIDE; PHENAZINE; PLATINUM COMPLEX; PLATINUM ETHYLENEDIAMINE DICHLORIDE; RNA POLYMERASE;

ARTICLE; ASSAY; BINDING SITE; CHEMICAL REACTION; DNA ADDUCT; DRUG DNA BINDING; DRUG SPECIFICITY; GENETIC TRANSCRIPTION; PRIORITY JOURNAL;

ANTINEOPLASTIC AGENTS; BINDING SITES; DNA; DNA-DIRECTED RNA POLYMERASES; DRUG STABILITY; KINETICS; ORGANOPLATINUM COMPOUNDS; PHENAZINES; SUBSTRATE SPECIFICITY;

EID: 0032840044     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. 195Pt NMR kinetic and mechanistic .studies of cis-and transdiamminedichloroplatinum(II) binding to DNA. Journal of the American Chemical Society, 112, 6860.
2. Behrens B.C., Hamilton T.C., Masuda H., Grotzinger K.R., Whang-Peng J., Louie K.G., Knutsen T., McKoy W.M., Yang R.C., Ozols R.F. (1987) Characterisation of a cis-diamminedichloroplatinum(II)-resistant human ovarian cell line and its use in evaluation of platinum analogues. Cancer Research, 47, 414.
3. Bowler B.E., Hollis L.S., Lippard S.J. (1984) Synthesis and DNA binding and photonicking properties of acridine orange linked by a polymethylene chain tether to (1,2-diaminoethane)dichloroplatinum(II). Journal of the American Chemical Society, 106, 6102.
4. Bruhn S.L., Toney J.H., Lippard S.J. (1990) Biological processing of DNA modified by platinum compounds. Progress in Inorganic Chemistry: Bioinorganic Chemistry, 38, 477.
5. Coley R.F., Martin D.S. (1973) Kinetics and equilibria for the acid hydrolysis of dichloro(ethylenediamine)platinum(II). Inorganica Chimica Acta, 7, 573.
6. Corden B.J. (1987) Reaction of platinum(II) antitumour agents with sulfhydral compounds and the implications for nephrotoxicity. Inorganica Chimica Acta, 137, 125.
7. Cullinane C., Phillips D.R. (1993) Thermal stability of DNA adducts induced by cyanomorpholinoadriamycin in vitro. Nucleic Acids Research, 21, 1857.
8. Cullinane C., Wickham G., McFadyen W.D., Denny W.A., Palmer B.D., Phillips D.R. (1993) The use of bidirectional footprinting to detect platinum-DNA crosslinks by acridine-tethered platinum diamine complexes and cisplatin. Nucleic Acids Research, 21, 393.
9. Eastman A. (1983) Characterisation of the adducts produced in DNA by cis-diamminedichlorplatinum(II) and cis-dichloro(ethylenediamine)platinum(II). Biochemistry, 22, 3927.
10. Eastman A. (1985) Interstrand crosslinks and sequence specificity in the reaction of cis-dichloro(ethylenediamine)-platinum(II) with DNA. Biochemistry, 24, 5027.
11. Eastman A. (1986) Reevaluation of interaction of cis-dichloro(ethylenediamine)platinum(II) with DNA. Biochemistry, 25, 3912.
12. Elmroth S.K.C., Lippard S.J. (1995) Surface and electrostatic contributions to DNA-promoted reactions of platinum(II) complexes with short oligonucleotides: a kinetic study. Inorganic Chemistry, 34, 5234.
13. Grimaldi K.A., McAdam S.R., Souhami R.L., Hartley J.A. (1994) DNA damage by anti-cancer agents resolved at the nucleotide level of a single copy gene: evidence for a novel binding site for cisplatin in cells. Nucleic Acids Research, 22, 2311.
14. Haiduc I., Silvestru C. (1990) Organometallics in Cancer Chemotherapy, Vol. 2: Transition Metal Compounds, p. 218. CRC Press: Boca Raton, FL.
15. Ivanov A.I., Christodoulou J., Parkinson J.A., Barnham K.J., Tucker A., Woodrow J., Sadler P.J. (1998) Cisplatin binding sites on human albumin. Journal of Biological Chemistry, 273, 14721.
16. Johnston G.L. (1966) Cis-dichloro(ethylenediamine)platinum(II). Inorganic Synthesis, 8, 242.
17. Lambert B., Jestin J.-L., Bréhin P., Oleykowski C., Yeung A.T., Mailliet P., Prétot C., Le Pecq J.-B., Jacquemin-Sablon A., Chottard J.-B. (1995) Binding of the Escherichia coli UvrAB proteins to the DNA mono-and diadducts of cis-[N-2-amino-N-2-methylamino-2,2,1-bicycloheptane]-dichloroplatinum(II) and cisplatin. Journal of Biological Chemistry, 270, 21251.
18. Lippard S.J. (1994) Metals in medicine. In Bioinorganic Chemistry. Bertini I., Gray H.B., Lippard S.J., Valentine J.S. (eds), p. 519. University Science Books: Mill Valley, CA.
19. Louie K.G., Behrens T.J., Kinsella T.J., Hamilton T.C., Grotzinger K.R., McKoy W.M., Winker M.A., Ozols R.F. (1985) Radiation survival parameters of antineoplastic drug-sensitive and -resistant human ovarian cancer cell lines and their modification by buthionine sulfoximine. Cancer Research, 45, 2110.
20. Passini A., Zunino F. (1987) New cisplatin analogues - on the way to better antitumour agents. Angewandte Chemie Supplement, 26, 615.
21. Phillips D.R., Crothers D.M. (1995) An in vitro transcription assay for probing drug-DNA interactions during active transcription of DNA. Methods in Molecular Biology, 37, 89.
22. Phillips D.R., White R.J., Trist H., Cullinane C., Dean D., Crothers C.M. (1990) New insight into drug-DNA interactions at individual drug binding sites probed by RNA-polymerase during active transcription of the DNA. Anti-Cancer Drug Design, 5, 21.
23. Pinto A.L., Lippard S.J. (1985) Binding of the antitumour drug cis-diammindichloroplatinum(II) (cisplatin) to DNA. Biochimica et Biophysica Acta, 780, 167.
24. Reedijk J. (1996) Improved understanding in platinum antitumour chemistry. Chemical Communications, 801.
25. Rosenberg B., Van Camp L., Trosko J.E., Mansour V.H. (1969) Platinum compounds: a new class of potent antitumour agents. Nature, 222, 385.
26. Sanderson B.J.S., Ferguson L., Denny W.A. (1996) Mutagenic and carcinogenic properties of platinum-based anticancer drugs. Mutation Research, 355, 59.
27. Skorobogaty A., White R.J., Phillips D.R., Reiss J.A. (1988) The 5′-CA DNA-sequence of daunomycin. FEBS Letters, 227, 103.
28. Sundquist W.L., Bancroft D.P., Chassot L., Lippard S.J. (1988) DNA promotes the reaction of cis-diamminedichloroplatinum(II) with the exocyclic amino groups of ethidium bromide. Journal of the American Chemical Society, 110, 8559.
29. Trist H., Phillips D.R. (1989) In vitro transcription analysis of the role of flanking sequence on the DNA sequence specificity of adriamycin. Nucleic Acids Research, 17, 3673.
30. Wakelin L.P.G., Waring M. (1990) DNA intercalating agents. In Comprehensive Medicinal Chemistry. Sommes P.G. (ed.), vol. 2, p.703. Pergamon Press: Oxford.
31. Wang K., Lu J., Li R. (1996) The events that occur when cisplatin encounters cells. Coordination Chemistry Review, 151, 53.
32. White R.J., Phillips D.R. (1988) Transcriptional analysis of multisite drug-DNA dissociation kinetics: delayed termination of transcription by actinomycin D. Biochemistry, 27, 9122.
33. White R.J., Phillips D.R. (1989) Bidirectional transcription footprinting of DNA binding ligands. Biochemistry, 28, 6259.
34. Whittaker J., McFadyen W.D., Wickham G., Wakelin L.P.G., Murray V. (1998) The interaction of DNA-targeted platinum phenanthridium complexes with DNA. Nucleic Acids Research, 26, 3933.