Activity and DNA binding of new organoamidoplatinum (II) complexes

Investigational New Drugs

Volumn 17, Issue 1, 1999, Pages 1-15

  Talarico, Teresa ^a,b   Phillips, Don R ^b   Deacon, Glen B ^c   Rainone, Silvina ^a   Webster, Lorraine K ^a  

^a PETER MACCALLUM CANCER CENTRE   (Australia)

^b LA TROBE UNIVERSITY   (Australia)

^c MONASH UNIVERSITY   (Australia)

Author keywords

Anticancer activity; Cell uptake; Cisplatin analogues; Dna interstrand crosslinks; In vitro transcription

Indexed keywords

ANTINEOPLASTIC METAL COMPLEX; PLATINUM COMPLEX;

ANIMAL CELL; ANIMAL EXPERIMENT; ANTINEOPLASTIC ACTIVITY; ARTICLE; CARCINOMA CELL; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DNA BINDING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA CELL; MOUSE; NONHUMAN; PRIORITY JOURNAL; TUMOR MODEL; TUMOR REGRESSION;

ANIMALS; ANTINEOPLASTIC AGENTS; AUTORADIOGRAPHY; BINDING SITES; CISPLATIN; CROSS-LINKING REAGENTS; DNA ADDUCTS; DRUG SCREENING ASSAYS, ANTITUMOR; DRUGS, INVESTIGATIONAL; FEMALE; HUMANS; LEUKEMIA L1210; MICE; TUMOR CELLS, CULTURED;

EID: 0032823247     PISSN: 01676997     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1006263917610     Document Type: Article

References (35)

1. Comis RL: Cisplatin: The future. Semin Oncol 21(Suppl 12): 109-113, 1994
2. Fram RJ: Cisplatin and platinum analogues: Recent advances. Current Opinions in Oncology 4: 1073-1079, 1992
3. Chao CCK: Molecular basis of cis-diamminedichloroplatinum(II) resistance: A review. J Formos Med Assoc 95: 893-901, 1996
4. Scanlon KJ, Kashani-Sabet M, Miyachi H, Sowers LC, Rossi J: Molecular basis of cisplatin resistance in human carcinomas: Model systems and patients. Anticancer Res 9: 1301-1312, 1989
5. Duffull SB, Robinson BA: Clinical pharmacokinetics and dose optimization of carboplatin. Clin Pharmacokinet 33: 161-183, 1997
6. Webster LK, Deacon GB, Buxton DP, Hillcoat BL, James AM, Roos IAG, Thomson RJ, Wakelin LPG, Williams TL: cis-Bis(pyridine)platinum(II) organoamides with unexpected growth inhibition properties and antitumour activity. J Med Chem 35: 3349-3353, 1992
7. Buxton DP, Deacon GB, Gatehouse BM, Grayson IL, Hillcoat GL, James AM, Knowles SJ, Roos IAG, Webster LK, Williams TL: 6th International Symposium on platinum and other metal coordination compounds in cancer chemotherapy, San Diego, CA: 191, 1991
8. Coluccia M, Nassi A, Loseto F, Boccarelli A, Mariggio MA, Giordano D, Intini FP, Caputo P, Natile G: A trans-platinum complex showing higher antitumour activity than the cis congeners. J Med Chem 36: 510-512, 1993
9. Kelland LR, Barnard CFJ, Mellish KJ, Jones M, Goddard PM, Valenti M, Bryant A, Murrer BA, Harrap KR: A novel trans-platinum coordination complex possessing in vitro and in vivo antitumour activity. Cancer Res 54: 5618-5622, 1994
10. Mellish KJ, Barnard CFJ, Kelland LR, Harrap KR: Circumvention of acquired tetraplatin resistance in a human ovarian carcinoma cell line by novel trans platinum complex. JM335 [Trans ammine (cyclohexylamine)dichloro dihydroxo platinum (IV)]. Int J Cancer 59: 65-70, 1994
11. Mellish KJ, Barnard CFJ, Murrer BA, Kelland LR: DNA-binding properties of novel cis- and trans platinum-based anticancer agents in two human ovarian carcinoma cell lines. Int J Cancer 62: 717-723, 1995
12. Farrell N: Transition Metal Complexes as Drugs and Chemotherapeutic Agents. Dordrecht: Kluwer Academic Publishers, 1989
13. Hambley TW: The influence of structure on the activity and toxicity of Pt anticancer drugs. Coordination Chem Rev 166: 181-223, 1997
14. Van der Veer JL, Reedijk J: Investigation of antitumour drug mechanisms. Chem Brit 20: 775-780, 1988
15. Reedijk J: The relevance of hydrogen bonding in the mechanism of action of platinum antitumour compounds. Inorg Chim Acta 198-200: 873-881, 1992
16. 195Pt NMR kinetic and mechanistic studies of cis- and trans-diamminedichloroplatinum(II) binding to DNA. J Am Chem Soc 112: 6860-6871, 1990
17. 2)I(py)]. Aust J Chem 44: 1669-1681, 1991
18. Buxton DP, Deacon GB, Gatehouse BM, Grayson IL, Black DStC: Organoamidometallics. II Decarboxylation syntheses and structures of [N,N-dimethyl,N′-(polyfluorophenyl)ethane-1,2-diaminato(1-)] platinum(II) complexes. Aust J Chem 41: 943-956, 1988
19. Bloemink MJ, Heetebrij RJ, Ireland J, Deacon GB, Reedijk J: DNA-binding properties of antitumor-active cis-bis(pyridine)platinum(II) organoamides. J Biol Inorg Chem 1: 278-283, 1996
20. Buxton DP, Deacon GB, Black DStC: Organoamidometallics-III. 2,6-Dimethylpyridine and 1,4-dioxan as a weakly coordinating polar solvents for decarboxylation syntheses of [N,N-dimethyl-N′-(polyfluorophenyl)ethane-1,2-diaminato(1-)] platinum(II) complexes. Polyhedron 8: 143-147, 1989
21. Chow A: Synthesis, properties and anticancer activity of organoamidoplatinum (II) complexes. Monash University, App Chem MSc Thesis, 1996
22. Rabinovich A: Synthesis of new organoamidoplatinum (II) anticancer agents. Monash University, BSc (Hons) Thesis, 1992
23. Sambrook J, Fritsch EF, Maniatis T: Molecular Cloning: A Laboratory Manual (Second edition) USA, Cold Spring Harbour Laboratory Press, 1989
24. Cullinane C, Van Rosmalen A, Phillips DR: Does adriamycin induce interstrand cross-links in DNA? Biochem 33: 4632-4638, 1994
25. Andrews PA, Murphy MP, Howell SB: Differential potentiation of alkylating and platinating agent cytotoxicity in human ovarian carcinoma cells by glutathione depletion. Cancer Res 45: 6250-6253, 1985
26. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR: New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst 82: 1107-1112, 1990
27. Cafaggi S, Esposito M, Parodi B, Vannozzi MO, Viale M, Pellecchia C, Fulco RA, Merlo F, Zicca A, Cadoni A et al.: Synthesis and antitumor activity of a new cis-diammineplatinum (II) complex containing procaine hydrochloride. Anticancer Res 12: 2285-2292, 1992
28. Viale M, Cafaggi S, Parodi B, Esposito M: Cytotoxicity and cellular accumulation of a new cis-diammineplatinum (II) complex containing procaine in murine L1210 cells sensitive and resistant to cis-diamminedichloroplatinum (II). Cancer Chemother Pharmacol 35: 371-376, 1995
29. Hartley JA, Bingham JP, Souhami RL: DNA sequence selectivity of guanine-N7 alkylation by nitrogen mustards is preserved in intact cells. Nucleic Acids Res 20: 3175-3178, 1992
30. White RJ, Phillips DR: Transcriptional analysis of multi-site drug-DNA dissociation kinetics: Delayed termination of transcription by actinomycin D. Biochem 27: 9122-9232, 1988
31. Phillips DR, Crothers DM: An in vitro transcription assay for probing drug-DNA interactions during active transcription of DNA. In: Tymms, MJ (ed) Methods in Molecular Biology: In vitro Transcription and Translation Protocols. Totowa, NJ: Humania Press Inc. pp 89-105, 1995
32. Goddard PM, Valenti MR, Harrap KR: The role of murine tumour models and their acquired platinum-resistant counterparts in the evaluation of novel antitumour agents: A cautionary note. Ann Oncol 2: 535-540, 1991
33. Murray V, Motyka H, England PR, Wickham G, Lee HH, Denny WA, McFadyen DW: The use of Taq DNA polymerase to determine the sequence specificity of DNA damage caused by cis-diamminedichloroplatinum(II), acridine-tethered platinum(II) diammine complexes or two analogues. J Biol Chem 267: 18805-18809, 1992
34. Knox RJ, Friedlos F, Lyndall DA, Roberts JJ: Mechanism of cytotoxicity of anticancer platinum drugs: Evidence that cis-diamminedichloroplatinum(II) and cis-diammine(1,1-cyclobutanedicarboxylato) platinum(II) differ only in the kinetics of their interaction with DNA. Cancer Res 46: 1972-1979, 1986
35. Pullman A, Pullman B: Molecular electrostatic potential of the nucleic acids. Quart Rev Biophys 14: 289-380, 1981