Pharmacological and molecular effects of platinum(II) complexes involving 7-azaindole derivatives

PLoS ONE

Volumn 9, Issue 3, 2014, Pages

  Štarha, Pavel ^a   Hošek, Jan ^a   Vančo, Ján ^a   Dvořák, Zdeněk ^a   Suchý Jr , Pavel ^b   Popa, Igor ^a   Pražanová, Gabriela ^b   Trávníček, Zdeněk ^a  

^a PALACKÝ UNIVERSITY   (Czech Republic)

^b UNIVERSITY OF VETERINARY AND PHARMACEUTICAL SCIENCES   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

3 CHLORO 7 AZAINDOLE PLATINUM COMPLEX; 3 IODO 7 AZAINDOLE PLATINUM COMPLEX; 5 BROMO 7 AZAINDOLE PLATINUM COMPLEX; 7 AZAINDOLE DERIVATIVE; ANTINEOPLASTIC AGENT; CASPASE 3; CASPASE 8; CISPLATIN; CYSTEINE; GLUTATHIONE; HUMAN SERUM ALBUMIN; INDOLE DERIVATIVE; PLATINUM COMPLEX; PROTEIN P53; UNCLASSIFIED DRUG; 7-AZAINDOLE DIMER;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CANCER RESISTANCE; CANCER TISSUE; CELL STRAIN A2780; CELL STRAIN A2780R; CELL STRAIN A549; CELL STRAIN G 361; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG SAFETY; DRUG STABILITY; DRUG SYNTHESIS; ENZYME REGULATION; EX VIVO STUDY; FEMALE; HELA CELL; HISTOPATHOLOGY; HUMAN; HUMAN CELL; HYDROLYSIS; IMMUNOHISTOCHEMISTRY; IN VITRO STUDY; IN VIVO STUDY; ISOTHERMAL TITRATION CALORIMETRY; LYMPHATIC LEUKEMIA; MITOCHONDRIAL RESPIRATION; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THERMODYNAMICS; TREATMENT DURATION; ANIMAL; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DBA MOUSE; DRUG EFFECTS; ELECTROSPRAY MASS SPECTROMETRY; HELA CELL LINE; KAPLAN MEIER METHOD; LEUKEMIA, LYMPHOID; MCF 7 CELL LINE; METABOLISM; PATHOLOGY; TREATMENT OUTCOME; TUMOR CELL LINE; WESTERN BLOTTING;

ANIMALS; ANTINEOPLASTIC AGENTS; BLOTTING, WESTERN; CASPASE 3; CASPASE 8; CELL LINE, TUMOR; CELL SURVIVAL; CISPLATIN; DRUG STABILITY; FEMALE; HELA CELLS; HUMANS; IMMUNOHISTOCHEMISTRY; INDOLES; KAPLAN-MEIER ESTIMATE; LEUKEMIA, LYMPHOID; MAGNETIC RESONANCE SPECTROSCOPY; MCF-7 CELLS; MICE, INBRED DBA; MOLECULAR STRUCTURE; ORGANOPLATINUM COMPOUNDS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; THERMODYNAMICS; TREATMENT OUTCOME; TUMOR SUPPRESSOR PROTEIN P53;

EID: 84897429084     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0090341     Document Type: Article

References (51)

1. Kelland L (2007) The resurgence of platinum-based cancer chemotherapy. Nature Rev Cancer 7: 573-584.
2. Kelland LR, Farrell NP (2000) Platinum-Based Drugs in Cancer Therapy. Humana: Totowa.
3. Rosenberg B, VanCamp L, Krigas T (1965) Inhibition of cell division in Escherichia coli by electrolysis products from a platinum electrode. Nature 205: 698-699.
4. Rosenberg B, VanCamp L, Trosko JE, Mansour VH (1969) Platinum compounds - a new class of potent antitumour agents. Nature 222: 385-386.
5. Harrap KR (1985) Preclinical studies identifying carboplatin as a viable cisplatin alternative. Cancer Treat Rev 12: 21-33.
6. Akaza H, Togashi M, Nishio Y, Miki T, Kotake T, et al. (1992) Phase II study of cis-diammine(glycolato)platinum, 254-S, in patients with advanced germ-cell testicular cancer, prostatic cancer, and transitional-cell carcinoma of the urinary tract. Cancer Chemother Pharmacol 31: 187-192.
7. Kidani Y, Inagaki K, Iigo M, Hoshi A, Kuretani K (1978) Anti-tumor activity of 1,2-diaminocyclohexaneplatinum complexes against sarcoma-180 ascites form. J Med Chem 21: 1315-1318. (Pubitemid 9093117)
8. McKeage MJ (2001) Lobaplatin: a new antitumour platinum drug. Expert Opin Inv Drugs 10: 119-128.
9. Shen DW, Pouliot LM, Hall MD, Gottesman MM (2012) Cisplatin Resistance: A Cellular Self-Defense Mechanism Resulting from Multiple Epigenetic and Genetic Changes. Pharmacol Rev 64: 706-721.
10. Galanski M, Yasemi A, Slaby S, Jakupec MA, Arion VB, et al. (2004) Synthesis, crystal structure and cytotoxicity of new oxaliplatin analogues indicating that improvement of anticancer activity is still possible. Eur J Med Chem 39: 707-714. (Pubitemid 38970085)
11. Holford J, Sharp SY, Murrer BA, Abrams M, Kelland LR (1998) In vitro circumvention of cisplatin resistance by the novel sterically hindered platinum complex AMD473. Br J Cancer 77: 366-373. (Pubitemid 28044038)
12. Holford J, Raynaud F, Murrer BA, Grimaldi K, Hartley JA, et al. (1998) Chemical, biochemical and pharmacological activity of the novel sterically hindered platinum coordination complex, cis-[amminedichloro(2-methylpyridine)] platinum(II) (AMD473). Anticancer Drug Design 13: 1-18. (Pubitemid 28045535)
13. Sharp SY, O'Neill CF, Rogers PM, Boxall FE, Kelland LR (2002) Retention of activity by the new generation platinum agent AMD0473 in four human tumour cell lines possessing acquired resistance to oxaliplatin. Eur J Cancer 38: 2309-2315. (Pubitemid 35346473)
14. Wheate NJ, Walker S, Craig GE, Oun R (2010) The status of platinum anticancer drugs in the clinic and in clinical trials. Dalton Trans 39: 8113-8127.
15. Pogozheva D, Baudrona SA, Rogez G, Hosseini MW (2013) From discrete tricyanovinylene appended 7-azaindole copper(II) paddlewheel to an infinite 1D network: Synthesis, crystal structure and magnetic properties. Polyhedron 52: 1329-1335.
16. Tsoureas N, Nunn J, Bevis T, Haddow MF, Hamilton A, et al. (2011) Strong agostic-type interactions in ruthenium benzylidene complexes containing 7-azaindole based scorpionate ligands. Dalton Trans 40: 951-958.
17. Ruiz J, Rodríguez V, de Haro C, Espinosa A, Péerez J, et al. (2010) New 7- azaindole palladium and platinum complexes: crystal structures and theoretical calculations. In vitro anticancer activity of the platinum compounds. Dalton Trans 39: 3290-3301.
18. Pierce LT, Cahill MM, Winfield HJ, McCarthy FO (2012) Synthesis and identification of novel indolo[2,3-a]pyrimido[5,4-c]carbazoles as a new class of anti-cancer agents. Eur J Med Chem 56: 292-300.
19. Hong S, Kim J, Seo JH, Jung KH, Hong SS, et al. (2012) Design, Synthesis, and Evaluation of 3,5-Disubstituted 7-Azaindoles as Trk Inhibitors with Anticancer and Antiangiogenic Activities. J Med Chem 55: 5337-5349.
20. Chevé G, Bories C, Fauvel B, Picot F, Tible A, et al. (2012) De novo design, synthesis and pharmacological evaluation of new azaindole derivatives as dual inhibitors of Abl and Src kinases. Med Chem Commun 3: 788-800.
21. Dyke HJ, Price S, Williams K (2010) US Patent 20100216768.
22. Štarha P, Marek J, Trávníček Z (2012) Cisplatin and oxaliplatin derivatives involving 7-azaindole: Structural characterisations. Polyhedron 33: 404-409.
23. Štarha P, Trávníček Z, Popa A, Popa I, Muchová T, et al. (2012) How to modify 7-azaindole to form cytotoxic Pt(II) complexes: Highly in vitro anticancer effective cisplatin derivatives involving halogeno-substituted 7-azaindole. J Inorg Biochem 115: 57-63.
24. Muchová T, Prachařová J, Štarha P, Olivová R, Vrána O, et al. (2013) Insight into the toxic effects of cis-dichloridoplatinum(II) complexes containing 7-azaindole halogeno derivatives in tumor cells. J Biol Inorg Chem 18: 579-589.
25. Salemi G, Gueli MC, D'Amelio M, Saia V, Mangiapane P, et al. (2009) Blood levels of homocysteine, cysteine, glutathione, folic acid, and vitamin B12 in the acute phase of atherothrombotic stroke. Neurol Sci 30: 361-364.
26. Trávníček Z, Matiková-Maarová M, Novotná R, Vančo J, ŠtěpánkováK, et al. (2011) In vitro and in vivo biological activity screening of Ru(III) complexes involving 6-benzylaminopurine derivates with higher pro-apoptotic activity than NAMI-A. J Inorg Biochem 105: 937-948.
27. Talhouk R, Chin J, Unemori E, Werb Z, Bissell M (1991) Proteinases of the mammary gland: developmental regulation in vivo and vectorial secretion in culture. Development 112: 439-49.
28. Reedijk J (1999) Why does cisplatin reach guanine-N7 with competing S-donor ligands available in the cell? Chem Rev 99: 2499-2510.
29. Nagle PS, Rodriguez F, Nguyen B, Wilson WD, Rozas I (2012) High DNA Affinity of a Series of Peptide Linked Diaromatic Guanidinium-like Derivatives. J Med Chem 55: 4397-4406.
30. Spuches AM, Kruszyna HG, Rich AM, Wilcox DE (2006) Thermodynamics of the As(III)-Thiol Interaction: Arsenite and Monomethylarsenite Complexes with Glutathione, Dihydrolipoic Acid, and Other Thiol Ligands. Inorg Chem 44: 2964-2972. (Pubitemid 40544998)
31. Timerbaev AR, Hartinger CG, Aleksenko SS, Keppler BK (2006) Interactions of Antitumour Metallodrugs with Serum Proteins: Advances in Characterization Using Modern Analytical Methodology. Chem Rev 106: 2224-2248.
32. Esposito BA, Najjar R (2002) Interactions of antitumoural platinum-group metallodrugs with albumin. Coord Chem Rev 232: 137-149.
33. Brown SD, Trotter KD, Sutcliffe OB, Plumb JA, Waddell B, et al. (2012) Combining aspects of the platinum anticancer drugs picoplatin and BBR3464 to synthesize a new family of sterically hindered dinuclear complexes; their synthesis, binding kinetics and cytotoxicity. Dalton Trans 41: 11330-11339.
34. 8 metals. Studies of their interactions with DNA and HSA. J Inorg Biochem 116: 204-214.
35. Quirante J, Ruiz D, Gonzalez A, López C, Cascante M, et al. (2011) Platinum(II) and palladium(II) complexes with (N,N9) and (C,N,N9)2 ligands derived from pyrazole as anticancer and antimalarial agents: Synthesis, characterization and in vitro activities. J Inorg Biochem 105: 1720-1728.
36. Carland M, Grannas MJ, Cairns MJ, Roknic VJ, Denny WA, et al. (2010) Substituted 9-aminoacridine-4-carboxamides tethered to platinum(II)diamine complexes: Chemistry, cytotoxicity and DNA sequence selectivity. J Inorg Biochem 104: 815-819.
37. Vrzal R, Štarha P, Dvořák Z, Trávní ček Z (2010) Evaluation of in vitro cytotoxicity and hepatotoxicity of platinum(II) and palladium(II) oxalato complexes with adenine derivatives as carrier ligands. J Inorg Biochem 104: 1130-1132.
38. de Mier-Vinué J, Gay M, Montaña AM, Sáez RI, Moreno V, et al. (2008) Synthesis, biophysical studies, and antiproliferative activity of platinum(II) complexes having 1,2-bis(aminomethyl)carbobicyclic ligands. J Med Chem 51: 424-431. (Pubitemid 351252271)
39. Yamori T (2003) Panel of human cancer cell lines provides valuable database for drug discovery and bioinformatics. Cancer Chemother Pharmacol 52: S74-S79.
40. Margiotta N, Denora N, Ostuni R, Laquintana V, Anderson A, et al. (2010) Platinum(II) complexes with bioactive carrier ligands having high affinity for the translocator protein. J Med Chem 53: 5144-5154.
41. Xu G, Yan Z, Wamg N, Liu Z (2011) Synthesis and cytotoxicity of cisdichloroplatinum (II) complexes of (1S,3S)-1,2,3,4-tetrahydroisoquinolines. Eur J Med Chem 46: 356-363.
42. Komeda S, Takayama H, Suzuki T, Odani A, Yamori T, et al. (2013) Synthesis of antitumour azolato-bridged dinuclear platinum(II) complexes within vivo antitumour efficacy and uniquein vitro cytotoxicity profiles. Metallomics 5: 461-468.
43. World Health Organization (2009) World Health Statistics 2009. Available: http://www.who.int/whosis/whostat/2009/en/. Accessed 2014 Feb 13.
44. Hua H, Li M, Luo T, Yin Y, Jiang Y (2011) Matrix metalloproteinases in tumourigenesis: an evolving paradigm. Cell Mol Life Sci 68: 3853-3868.
45. Zhang B, Ramesh G, Uematsu S, Akira S, Reevers WB (2008) TLR4 Signaling Mediates Inflammation and Tissue Injury in Nephrotoxicity. J Am Soc Nephrol 19: 923-932.
46. Reedijk J (1987) The mechanism of action of platinum anti-tumor drugs. Pure Appl Chem 59: 181-192.
47. Siddik ZH (2003) Cisplatin: mode of cytotoxic action and molecular basis of resistance. Oncogene 22: 7265-7279. (Pubitemid 37487159)
48. Agarwal ML, Taylor WR, Chernov MV, Chernova OB, Stark GR (1998) The p53 Network. J Biol Chem 273: 1-4. (Pubitemid 28042164)
49. Gong JG, Costanzo A, Yang HQ, Melino G, Kaelin WG, et al. (1999) The tyrosine kinase c-Abl regulates p73 in apoptotic response to cisplatin-induced DNA damage. Nature 399: 806-809. (Pubitemid 29293179)
50. Hengartner MO (2000) The biochemistry of apoptosis. Nature 407: 770-776.
51. Chauhan P, Sodhi A, Shrivastava A (2009) Cisplatin primes murine peritoneal macrophages for enhanced expression of nitric oxide, proinflammatory cytokines, TLRs, transcription factors and activation of MAP kinases upon coincubation with L929cells. Immunobiology 214: 197-209.