Understanding and improving platinum anticancer drugs - Phenanthriplatin

Anticancer Research

Volumn 34, Issue 1, 2014, Pages 471-476

  Johnstone, Timothy C ^a   Park, Ga Young ^a   Lippard, Stephen J ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

Cytotoxicity; Monofunctional platinum; Pyriplatin; Review; RNA polymerase II; Transcription; X ray structure

Indexed keywords

ANTINEOPLASTIC AGENT; CHLORIDE ION; CISPLATIN; CISPLATIN DERIVATIVE; DNA; PHENANTHRIPLATIN; PLATINUM; RNA POLYMERASE II; UNCLASSIFIED DRUG; PHENANTHRIDINE DERIVATIVE; PLATINUM COMPLEX;

ANTINEOPLASTIC ACTIVITY; CANCER CELL; CELL ASSAY; CONFERENCE PAPER; CRYSTAL STRUCTURE; HUMAN; STRUCTURE ACTIVITY RELATION; CYTOTOXICITY; MONOFUNCTIONAL PLATINUM; NEOPLASM; PROGNOSIS; PYRIPLATIN; REVIEW; TRANSCRIPTION; X-RAY STRUCTURE;

CYTOTOXICITY; MONOFUNCTIONAL PLATINUM; PYRIPLATIN; REVIEW; RNA POLYMERASE II; TRANSCRIPTION; X-RAY STRUCTURE;

ANTINEOPLASTIC AGENTS; HUMANS; NEOPLASMS; ORGANOPLATINUM COMPOUNDS; PHENANTHRIDINES; PROGNOSIS;

EID: 84893797059     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Conference Paper

References (44)

1. Galanski M, Jakupec MA and Keppler BK: Update of the preclinical situation of anticancer platinum complexes: Novel design strategies and innovative analytical approaches. Curr Med Chem 12: 2075-2094, 2005.
2. Rosenberg B, VanCamp L, Trosko JE and Mansour VH: Platinum compounds: A new class of potent antitumour agents. Nature 222: 385-386, 1969.
3. Brabec V and Kasparkova J: Modifications of DNA by platinum complexes: Relation to resistance of tumors to platinum antitumor drugs. Drug Resist Updat 8: 131-146, 2005.
4. Chabner BA and Roberts TG Jr.: Chemotherapy and the war on cancer. Nat Rev Cancer 5: 65-72, 2005.
5. Kelland L: The resurgence of platinum-based cancer chemotherapy. Nat Rev Cancer 7: 573-584, 2007.
6. Lovejoy KS and Lippard SJ: Non-traditional platinum compounds for improved accumulation, oral bioavailability, and tumor targeting. Dalton Trans 10651-10659, 2009.
7. Park GY, Wilson JJ, Song Y and Lippard SJ: Phenanthriplatin, a monofunctional DNA-binding platinum anticancer drug candidate with unusual potency and cellular activity profile. Proc Natl Acad Sci USA 109: 11987-11992, 2012.
8. Peyrone M: Ueber die Einwirkung des Ammoniaks auf Platinchlorür. Liebigs Ann 51: 1-29, 1844.
9. Rosenberg B: Platinum complexes for the treatment of cancer: Why the search goes on. In: Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug. Lippert B (ed.). Zürich, Verlag Helvetica Chimica Acta, pp. 1-27, 1999.
10. Smith GH: New drugs released in 1978. Nurse Pract 4: 35-41, 1979.
11. Hoeschele JD: In remembrance of Barnett Rosenberg. Dalton Trans 10648-10650, 2009.
12. Cleare MJ and Hoeschele JD: Studies on the antitumor activity of group VIII transition metal complexes. Part I. Platinum(II) complexes. Bioinorg Chem 2: 187-210, 1973.
13. Wheate NJ, Walker S, Craig GE and Oun R: The status of platinum anticancer drugs in the clinic and in clinical trials. Dalton Trans 39: 8113-8127, 2010.
14. Wang D and Lippard SJ: Cellular processing of platinum anticancer drugs. Nat Rev Drug Discov 4: 307-320, 2005.
15. Gately DP and Howell SB: Cellular accumulation of the anticancer agent cisplatin - A review. Br J Cancer 67: 1171-1176, 1993.
16. Howell SB, Safaei R, Larson CA and Sailor MJ: Copper transporters and the cellular pharmacology of the platinum-containing cancer drugs. Mol Pharmacol 77: 887-894, 2010.
17. Ivy KD and Kaplan JH: A re-evaluation of the role of hCTR1, the human high-affinity copper transporter, in platinum-drug entry into human cells. Mol Pharmacol 83: 1237-1246, 2013.
18. Zhang S, Lovejoy KS, Shima JE, Lagpacan LL, Shu Y, Lapuk A, Chen Y, Komori T, Gray JW, Chen X, Lippard SJ and Giacomini KM: Organic cation transporters are determinants of oxaliplatin cytotoxicity. Cancer Res 66: 8847-8857, 2006.
19. Pil P and Lippard SJ: Cisplatin and related drugs. In: Encyclopedia of Cancer. Joseph RB (ed.). New York, Academic Press, pp. 525-543, 2002.
20. Di Pasqua AJ, Goodisman J, Kerwood DJ, Toms BB, Dubowy RL and Dabrowiak JC: Activation of carboplatin by carbonate. Chem Res Toxicol 19: 139-149, 2006.
21. Todd RC, Lovejoy KS and Lippard SJ: Understanding the effect of carbonate ion on cisplatin binding to DNA. J Am Chem Soc 129: 6370-6371, 2007.
22. Takahara PM, Rosenzweig AC, Frederick CA and Lippard SJ: Crystal-structure of double-stranded DNA containing the major adduct of the anticancer drug cisplatin. Nature 377: 649-652, 1995.
23. Von Hoff DD, Schilsky R, Reichert CM, Reddick RL, Rozencweig M, Young RC and Muggia FM: Toxic effects of cis-dichlorodiammineplatinum(II) in man. Cancer Treat Rep 63: 1527-1531, 1979.
24. Coates A, Abraham S, Kaye SB, Sowerbutts T, Frewin C, Fox RM and Tattersall MH: On the receiving end - patient perception of the side-effects of cancer chemotherapy. Eur J Cancer Clin Oncol 19: 203-208, 1983.
25. Griffin AM, Butow PN, Coates AS, Childs AM, Ellis PM, Dunn SM and Tattersall MH: On the receiving end V: Patient perceptions of the side-effects of cancer chemotherapy in 1993. Ann Oncol 7: 189-195, 1996.
26. Martin LP, Hamilton TC and Schilder RJ: Platinum resistance: The role of DNA repair pathways. Clin Cancer Res 14: 1291-1295, 2008.
27. Coluccia M and Natile G: Trans-platinum complexes in cancer therapy. Anticancer Agents Med Chem 7: 111-123, 2007.
28. Wheate NJ and Collins JG: Multi-nuclear platinum complexes as anticancer drugs. Coordin Chem Rev 241: 133-145, 2003.
29. Bednarski PJ, Mackay FS and Sadler PJ: Photoactivatable platinum complexes. Anticancer Agents Med Chem 7: 75-93, 2007.
30. Baruah H, Barry CG and Bierbach U: Platinum-intercalator conjugates: From DNA-targeted cisplatin derivatives to adenine binding complexes as potential modulators of gene regulation. Curr Top Med Chem 4: 1537-1549, 2004.
31. Johnstone TC, Wilson JJ and Lippard SJ: Monofunctional and higher-valent platinum anticancer agents. Inorg Chem 52: 12234-12249, 2013.
32. Hall MD and Hambley TW: Platinum(IV) antitumour compounds: Their bioinorganic chemistry. Coordin Chem Rev 232: 49-67, 2002.
33. Lovejoy KS, Todd RC, Zhang S, McCormick MS, D'Aquino JA, Reardon JT, Sancar A, Giacomini KM and Lippard SJ: Cis-diammine(pyridine)chloroplatinum(II), a monofunctional platinum(II) antitumor agent: Uptake, structure, function, and prospects. Proc Natl Acad Sci USA 105: 8902-8907, 2008.
34. + bound to deoxyguanosine in a dodecamer duplex. In: Platinum and Other Heavy Metal Compounds in Cancer Chemotherapy. Bonetti A, Leone R, Muggia FM, Howell SB (eds.). New York, Humana Press, pp. 67-72, 2009.
35. Lovejoy KS, Serova M, Bieche I, Emami S, D'Incalci M, Broggini M, Erba E, Gespach C, Cvitkovic E, Faivre S, Raymond E and Lippard SJ: Spectrum of cellular responses to pyriplatin, a monofunctional cationic antineoplastic platinum(II) compound, in human cancer cells. Mol Cancer Ther 10: 1709-1719, 2011.
36. Jung Y and Lippard SJ: RNA polymerase II blockage by cisplatin-damaged DNA. Stability and polyubiquitylation of stalled polymerase. J Biol Chem 281: 1361-1370, 2006.
37. Ang WH, Brown WW and Lippard SJ: Preparation of mammalian expression vectors incorporating site-specifically platinated-DNA lesions. Bioconjug Chem 20: 1058-1063, 2009.
38. Ang WH, Myint M and Lippard SJ: Transcription inhibition by platinum-DNA cross-links in live mammalian cells. J Am Chem Soc 132: 7429-7435, 2010.
39. Zhu G, Myint M, Ang WH, Song L and Lippard SJ: Monofunctional platinum-DNA adducts are strong inhibitors of transcription and substrates for nucleotide excision repair in live mammalian cells. Cancer Res 72: 790-800, 2012.
40. Wang D, Zhu G, Huang X and Lippard SJ: X-Ray structure and mechanism of RNA polymerase II stalled at an antineoplastic monofunctional platinum-DNA adduct. Proc Natl Acad Sci USA 107: 9584-9589, 2010.
41. Damsma GE, Alt A, Brueckner F, Carell T and Cramer P: Mechanism of transcriptional stalling at cisplatin-damaged DNA. Nat Struct Mol Biol 14: 1127-1133, 2007.
42. Shoemaker RH: The NCI60 human tumour cell line anticancer drug screen. Nat Rev Cancer 6: 813-823, 2006.
43. Chen Y, Guo ZJ, Parkinson JA and Sadler PJ: Kinetic control of reactions of a sterically hindered platinum picoline anticancer complex with guanosine 5′-monophosphate and glutathione. J Chem Soc Dalton Trans 3577-3585, 1998.
44. Howe-Grant M, Wu KC, Bauer WR and Lippard SJ: Binding of platinum and palladium metallointercalation reagents and antitumor drugs to closed and open DNAs. Biochemistry 15: 4339-4346, 1976.