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Volumn 48, Issue 18, 2005, Pages 5651-5654

Enhancement of aqueous solubility and stability employing a trans acetate axis in trans planar amine platinum compounds while maintaining the biological profile

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; AMINE; CARBOPLATIN; CARBOXYLIC ACID; CHLORIDE; CISPLATIN; CYTOTOXIC AGENT; LIGAND; NITROGEN DIOXIDE; OXALIPLATIN; PLATINUM DERIVATIVE; TRANSPLATIN; WATER;

EID: 24744432080     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050539d     Document Type: Article
Times cited : (58)

References (40)
  • 1
    • 0003952947 scopus 로고    scopus 로고
    • Teicher, B. A., Ed.; Cancer Drug Discovery and Development; Humana Press: Totowa, NJ
    • Kelland, L. R., Farrell, N., Eds. Platinum-Based Drugs in Cancer Therapy; Teicher, B. A., Ed.; Cancer Drug Discovery and Development; Humana Press: Totowa, NJ, 2000.
    • (2000) Platinum-Based Drugs in Cancer Therapy
    • Kelland, L.R.1    Farrell, N.2
  • 2
    • 0003138007 scopus 로고    scopus 로고
    • DeVita, V. T., Hellman, S., Rosenberg, S. A., Eds.; Lippincott-Raven Publishers: Philadelphia, PA
    • O'Dwyer, P. J.; Johnson, S. W.; Hamilton, T. C. Cisplatin and Its Analogues, 5th ed.; DeVita, V. T., Hellman, S., Rosenberg, S. A., Eds.; Lippincott-Raven Publishers: Philadelphia, PA, 1997; Vol. 2, pp 418-431.
    • (1997) Cisplatin and Its Analogues, 5th Ed. , vol.2 , pp. 418-431
    • O'Dwyer, P.J.1    Johnson, S.W.2    Hamilton, T.C.3
  • 4
    • 24644486532 scopus 로고    scopus 로고
    • Current status of platinum-based antitumor drugs
    • Wong, E.; Giandomenico, C. M. Current status of platinum-based antitumor drugs. Chem. Rev. 1999, 99, 2451-2466.
    • (1999) Chem. Rev. , vol.99 , pp. 2451-2466
    • Wong, E.1    Giandomenico, C.M.2
  • 5
    • 0027186148 scopus 로고
    • Nonclassical platinum antitumor agents: Perspectives for design and development of new drugs complementary to cisplatin
    • Farrell, N. Nonclassical platinum antitumor agents: perspectives for design and development of new drugs complementary to cisplatin. Cancer Invest. 1993, 11, 578-589.
    • (1993) Cancer Invest. , vol.11 , pp. 578-589
    • Farrell, N.1
  • 6
    • 0011773101 scopus 로고    scopus 로고
    • Phase II clinical study of BBR 3464, a novel, bifunctional platinum analogue, in patients with advanced ovarian cancer
    • Poster 182
    • Calvert, A. H.; Thomas, H.; Colombo, N.; Gore, M.; Earl, H.; Sena, L.; Camboni, G.; Liati, P.; Sessa, C. Phase II clinical study of BBR 3464, a novel, bifunctional platinum analogue, in patients with advanced ovarian cancer. Eur. J. Cancer 2001, 37 (Suppl. 6), Poster 182.
    • (2001) Eur. J. Cancer , vol.37 , Issue.SUPPL. 6
    • Calvert, A.H.1    Thomas, H.2    Colombo, N.3    Gore, M.4    Earl, H.5    Sena, L.6    Camboni, G.7    Liati, P.8    Sessa, C.9
  • 7
    • 3042703868 scopus 로고    scopus 로고
    • Polynuclear platinum drugs
    • Farrell, N. Polynuclear platinum drugs. Met. Ions Biol. Syst. 2004, 42, 251-296.
    • (2004) Met. Ions Biol. Syst. , vol.42 , pp. 251-296
    • Farrell, N.1
  • 8
    • 0029688173 scopus 로고    scopus 로고
    • Current status of structure-activity relationships of platinum anticancer drugs: Activation of the trans geometry
    • Farrell, N. Current status of structure-activity relationships of platinum anticancer drugs: activation of the trans geometry. Met. Ions Biol. Syst. 1996, 32, 251-296.
    • (1996) Met. Ions Biol. Syst. , vol.32 , pp. 251-296
    • Farrell, N.1
  • 9
    • 4644221515 scopus 로고    scopus 로고
    • Platinum complexes with imino ethers or cyclic ligands mimicking imino ethers: Synthesis, in vitro antitumour activity, and DNA interaction properties
    • Intini, F. P.; Boccarelli, A.; Francia, V. C.; Pacifico, C.; Sivo, M. F.; Natile, G.; Giordano, D.; Rinaldis, P.; Coluccia, M. Platinum complexes with imino ethers or cyclic ligands mimicking imino ethers: synthesis, in vitro antitumour activity, and DNA interaction properties. J. Biol. Inorg. Chem. 2004, 9, 768-780.
    • (2004) J. Biol. Inorg. Chem. , vol.9 , pp. 768-780
    • Intini, F.P.1    Boccarelli, A.2    Francia, V.C.3    Pacifico, C.4    Sivo, M.F.5    Natile, G.6    Giordano, D.7    Rinaldis, P.8    Coluccia, M.9
  • 10
    • 0033560940 scopus 로고    scopus 로고
    • Crystal structure of a double-stranded DNA containing a cisplatin interstrand cross-link at 1.63 Å resolution: Hydration at the platinated site
    • Coste, F.; Malinge, J. M.; Serre, L.; Shepard, W.; Roth, M.; Leng, M.; Zelwer, C. Crystal structure of a double-stranded DNA containing a cisplatin interstrand cross-link at 1.63 Å resolution: hydration at the platinated site. Nucleic Acids Res. 1999, 27, 1837-1846.
    • (1999) Nucleic Acids Res. , vol.27 , pp. 1837-1846
    • Coste, F.1    Malinge, J.M.2    Serre, L.3    Shepard, W.4    Roth, M.5    Leng, M.6    Zelwer, C.7
  • 11
    • 0029585833 scopus 로고
    • Solution structure of a cisplatin-induced DNA interstrand cross-link
    • Huang, H.; Zhu, L.; Reid, B. R.; Drobny, G. P.; Hopkins, P. B. Solution structure of a cisplatin-induced DNA interstrand cross-link. Science 1995, 270, 1842-1845.
    • (1995) Science , vol.270 , pp. 1842-1845
    • Huang, H.1    Zhu, L.2    Reid, B.R.3    Drobny, G.P.4    Hopkins, P.B.5
  • 12
    • 0027301069 scopus 로고
    • DNA interstrand cross-links of trans-diamminedichloroplatinum(II) are preferentially formed between guanine and complementary cytosine residues
    • Brabec, V.; Leng, M. DNA interstrand cross-links of trans- diamminedichloroplatinum(II) are preferentially formed between guanine and complementary cytosine residues. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 5345-5349.
    • (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 5345-5349
    • Brabec, V.1    Leng, M.2
  • 13
    • 0035400494 scopus 로고    scopus 로고
    • Recognition of cisplatin adducts by cellular proteins
    • Kartalou, M.; Essigmann, J. M. Recognition of cisplatin adducts by cellular proteins. Mutat. Res. 2001, 478, 1-21.
    • (2001) Mutat. Res. , vol.478 , pp. 1-21
    • Kartalou, M.1    Essigmann, J.M.2
  • 14
    • 2542422438 scopus 로고    scopus 로고
    • Structure, recognition, and processing of cisplatin-DNA adducts
    • Jamieson, E. R.; Lippard, S. J. Structure, recognition, and processing of cisplatin-DNA adducts. Chem. Rev. 1999, 99, 2467-2498.
    • (1999) Chem. Rev. , vol.99 , pp. 2467-2498
    • Jamieson, E.R.1    Lippard, S.J.2
  • 15
    • 25544433774 scopus 로고
    • Activation of the trans geometry in platinum antitumor complexes. Synthesis, characterization, and biological activity of complexes with the planar ligands pyridine, N-methylimidazole, thiazole, and quinoline. Crystal and molecular structure of trans-dichlorobis(thiazole)platinum(II)
    • van Beusichem, M.; Farrell, N. Activation of the trans geometry in platinum antitumor complexes. Synthesis, characterization, and biological activity of complexes with the planar ligands pyridine, N-methylimidazole, thiazole, and quinoline. Crystal and molecular structure of trans- dichlorobis(thiazole)platinum(II). Inorg. Chem. 1992, 31, 634-639.
    • (1992) Inorg. Chem. , vol.31 , pp. 634-639
    • Van Beusichem, M.1    Farrell, N.2
  • 16
    • 0026803014 scopus 로고
    • Activation of the trans geometry in platinum antitumor complexes: A survey of the cytotoxicity of trans complexes containing planar ligands in murine L1210 and human tumor panels and studies on their mechanism of action
    • Farrell, N.; Kelland, L. R.; Roberts, J. D.; van Beusichem, M. Activation of the trans geometry in platinum antitumor complexes: a survey of the cytotoxicity of trans complexes containing planar ligands in murine L1210 and human tumor panels and studies on their mechanism of action. Cancer Res. 1992, 52, 5056-5072.
    • (1992) Cancer Res. , vol.52 , pp. 5056-5072
    • Farrell, N.1    Kelland, L.R.2    Roberts, J.D.3    Van Beusichem, M.4
  • 17
    • 0029121585 scopus 로고
    • DNA-binding properties of novel cis- And trans-platinum-based anticancer agents in 2 human ovarian carcinoma cell lines
    • Hellish, K. J.; Barnard, C. F. J.; Murrer, B. A.; Kelland, L. R. DNA-binding properties of novel cis- and trans-platinum-based anticancer agents in 2 human ovarian carcinoma cell lines. Int. J. Cancer 1995, 62, 717-723.
    • (1995) Int. J. Cancer , vol.62 , pp. 717-723
    • Hellish, K.J.1    Barnard, C.F.J.2    Murrer, B.A.3    Kelland, L.R.4
  • 19
    • 0037153213 scopus 로고    scopus 로고
    • Novel apoptosis-inducing trans-platinum piperidine derivatives: Synthesis and biological characterization
    • Khazanov, E.; Barenholz, Y.; Gibson, D.; Najajreh, Y. Novel apoptosis-inducing trans-platinum piperidine derivatives: synthesis and biological characterization. J. Med. Chem. 2002, 45, 5196-204.
    • (2002) J. Med. Chem. , vol.45 , pp. 5196-5204
    • Khazanov, E.1    Barenholz, Y.2    Gibson, D.3    Najajreh, Y.4
  • 20
    • 0037153219 scopus 로고    scopus 로고
    • Novel soluble cationic trans-diaminedichloroplatinum(II) complexes that are active against cisplatin resistant ovarian cancer cell lines
    • Najajreh, Y.; Perez, J. M.; Navarro-Ranninger, C.; Gibson, D. Novel soluble cationic trans-diaminedichloroplatinum(II) complexes that are active against cisplatin resistant ovarian cancer cell lines. J. Med. Chem. 2002, 45, 5189-5195.
    • (2002) J. Med. Chem. , vol.45 , pp. 5189-5195
    • Najajreh, Y.1    Perez, J.M.2    Navarro-Ranninger, C.3    Gibson, D.4
  • 21
    • 0036357321 scopus 로고    scopus 로고
    • DNA modifications by antitumor platinum and ruthenium compounds: Their recognition and repair
    • Brabec, V. DNA modifications by antitumor platinum and ruthenium compounds: their recognition and repair. Prog. Nucleic Acid Res. Mol. Biol. 2002, 71, 1-68.
    • (2002) Prog. Nucleic Acid Res. Mol. Biol. , vol.71 , pp. 1-68
    • Brabec, V.1
  • 23
    • 0034189944 scopus 로고    scopus 로고
    • 3)]: Unprecedented inversion of the cis-geometry requirement for platinum-based antitumor complexes
    • 3)]: Unprecedented inversion of the cis-geometry requirement for platinum-based antitumor complexes. Inorg. Chem. 2000, 39, 1882-1890.
    • (2000) Inorg. Chem. , vol.39 , pp. 1882-1890
    • Bierbach, U.1    Sabat, M.2    Farrell, N.3
  • 24
    • 23244452191 scopus 로고    scopus 로고
    • Pyridine-carboxylate complexes of platinum. Effect of N,O-chelate formation on model bifunctional DNA-DNA and DNA-protein interactions
    • Quintal, S. M. O.; Qu, Y.; Gomez-Quiroga, A.; Moniodis, J.; Nogueira, H. I. S.; Farrell, N. Pyridine-carboxylate complexes of platinum. Effect of N,O-chelate formation on model bifunctional DNA-DNA and DNA-protein interactions. Inorg. Chem. 2005, 44, 5247-5253.
    • (2005) Inorg. Chem. , vol.44 , pp. 5247-5253
    • Quintal, S.M.O.1    Qu, Y.2    Gomez-Quiroga, A.3    Moniodis, J.4    Nogueira, H.I.S.5    Farrell, N.6
  • 25
    • 0031774413 scopus 로고    scopus 로고
    • 3, quinoline): Implications for the mechanism of action of nonclassical trans-platinum antitumor complexes
    • 3, quinoline): implications for the mechanism of action of nonclassical trans-platinum antitumor complexes. J. Biol. Inorg. Chem. 1998, 3, 570-580.
    • (1998) J. Biol. Inorg. Chem. , vol.3 , pp. 570-580
    • Bierbach, U.1    Farrell, N.2
  • 26
    • 37049080162 scopus 로고
    • A rapid method for the synthesis of water-soluble platinum(II) amine and pyridine complexes
    • Souchard, J. P.; Wimmer, F. L.; Ha, T. T. B.; Johnson, N. P. A rapid method for the synthesis of water-soluble platinum(II) amine and pyridine complexes. J. Chem. Soc., Dalton Trans. 1990, 307-310.
    • (1990) J. Chem. Soc., Dalton Trans. , pp. 307-310
    • Souchard, J.P.1    Wimmer, F.L.2    Ha, T.T.B.3    Johnson, N.P.4
  • 27
    • 24744454206 scopus 로고    scopus 로고
    • note
    • 3CN 15:85).
  • 29
    • 0001241804 scopus 로고
    • Aspects of the solution chemistry of trans-diammineplatinum(II) complexes
    • Appleton, T. G.; Bailey, A. J.; Barnham, K. J.; Hall, J. R. Aspects of the solution chemistry of trans-diammineplatinum(II) complexes. Inorg. Chem. 1992, 31, 3077-3082.
    • (1992) Inorg. Chem. , vol.31 , pp. 3077-3082
    • Appleton, T.G.1    Bailey, A.J.2    Barnham, K.J.3    Hall, J.R.4
  • 30
    • 27544452085 scopus 로고    scopus 로고
    • II diamine anticancer compounds: Hydrolysis studies of picoline complexes
    • in press
    • II diamine anticancer compounds: hydrolysis studies of picoline complexes. Inorg. Chem., in press.
    • Inorg. Chem.
    • McGowan, G.1    Parsons, S.2    Sadler, P.J.3
  • 31
    • 37049090053 scopus 로고
    • Kinetics of the displacement of cyclobutane-1,1-dicarboxylate from diammine(cyclobutane-1,1-dicarboxylato)platinum(II) in aqueous solution
    • Canovese, L.; Cattalini, L.; Chessa, G.; Tobe, M. L. Kinetics of the displacement of cyclobutane-1,1-dicarboxylate from diammine(cyclobutane-1,1- dicarboxylato)platinum(II) in aqueous solution. J. Chem Soc., Dalton Trans. 1988, 2135-2140.
    • (1988) J. Chem Soc., Dalton Trans. , pp. 2135-2140
    • Canovese, L.1    Cattalini, L.2    Chessa, G.3    Tobe, M.L.4
  • 33
    • 0344012932 scopus 로고    scopus 로고
    • Hydrolysis triggers oxidation of a trans diamine platinum(II) anticancer complex
    • Pizarro, A. M.; Munk, V. P.; Navarro-Ranninger, C.; Sadler, P. J. Hydrolysis triggers oxidation of a trans diamine platinum(II) anticancer complex. Angew. Chem., Int. Ed. 2003, 42, 5339-5342.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 5339-5342
    • Pizarro, A.M.1    Munk, V.P.2    Navarro-Ranninger, C.3    Sadler, P.J.4
  • 34
    • 0001623268 scopus 로고
    • The hydrolysis products of cis-diammine-dichloroplatinum(II). 2. The kinetics and formation and anation of the cis-diamminedi(aqua)platinum(II) cation
    • Miller, S. E.; House, D. A. The hydrolysis products of cis-diammine-dichloroplatinum(II). 2. The kinetics and formation and anation of the cis-diamminedi(aqua)platinum(II) cation. Inorg. Chim. Acta 1989, 166, 189-197.
    • (1989) Inorg. Chim. Acta , vol.166 , pp. 189-197
    • Miller, S.E.1    House, D.A.2
  • 35
    • 0022000389 scopus 로고
    • Role of ligand exchange processes in the reaction kinetics of the antitumor drug cis-diaminedichloroplatinum(II) with its targets
    • Segal, E.; Le Pecq, J. B. Role of ligand exchange processes in the reaction kinetics of the antitumor drug cis-diaminedichloroplatinum(II) with its targets. Cancer Res. 1985, 45, 492-497.
    • (1985) Cancer Res. , vol.45 , pp. 492-497
    • Segal, E.1    Le Pecq, J.B.2
  • 36
    • 0000494557 scopus 로고
    • +. Determination of the rate constants using UV spectrophotometry
    • +. Determination of the rate constants using UV spectrophotometry. Inorg. Chem. Commun. 1988, 1, 439-445.
    • (1988) Inorg. Chem. Commun. , vol.1 , pp. 439-445
    • Marti, N.1    Hoa, G.H.2    Kozelka, J.3
  • 37
    • 37049090053 scopus 로고
    • Kinetics of the displacement of cyclobutane-1,1-dicarboxylate from diammine(cyclobutane-1,1-dicarboxylato)platinum(II) in aqueous solution
    • Canovese, L.; Cattalini, L.; Chessa, G.; Tobe, M. L. Kinetics of the displacement of cyclobutane-1,1-dicarboxylate from diammine(cyclobutane-1,1- dicarboxylato)platinum(II) in aqueous solution. J. Chem. Soc., Dalton Trans. 1988, 2135-2140.
    • (1988) J. Chem. Soc., Dalton Trans. , pp. 2135-2140
    • Canovese, L.1    Cattalini, L.2    Chessa, G.3    Tobe, M.L.4
  • 39
    • 24744450391 scopus 로고    scopus 로고
    • Accumulation of novel transplatinum complexes in cisplatin and oxaliplatin resistant cell lines overcomes resistance
    • Murphy, R. F.; Farrell, N.; Aguila, A.; Okada, M.; Balis, F. M.; Fojo, T. Accumulation of novel transplatinum complexes in cisplatin and oxaliplatin resistant cell lines overcomes resistance. Proc. Am. Assoc. Cancer Res. 2005, 46, 4109.
    • (2005) Proc. Am. Assoc. Cancer Res. , vol.46 , pp. 4109
    • Murphy, R.F.1    Farrell, N.2    Aguila, A.3    Okada, M.4    Balis, F.M.5    Fojo, T.6
  • 40
    • 10644259645 scopus 로고    scopus 로고
    • Identification of non-cross-resistant platinum compounds with novel cytotoxicity profiles using the NCI anticancer drug screen and clustered image map visualizations
    • Fojo, T.; Farrell, N.; Orthuzar, W.; Tanimura, H.; Stein, J.; Myers, T. G. Identification of non-cross-resistant platinum compounds with novel cytotoxicity profiles using the NCI anticancer drug screen and clustered image map visualizations. Crit. Rev. Hematol. Oncol. 2005, 53, 25-34.
    • (2005) Crit. Rev. Hematol. Oncol. , vol.53 , pp. 25-34
    • Fojo, T.1    Farrell, N.2    Orthuzar, W.3    Tanimura, H.4    Stein, J.5    Myers, T.G.6


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