메뉴 건너뛰기




Volumn 55, Issue 17, 2012, Pages 7817-7827

Synthesis, aqueous reactivity, and biological evaluation of carboxylic acid ester-functionalized platinum-acridine hybrid anticancer agents

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE; ANTINEOPLASTIC AGENT; CARBOXYLIC ACID; CHLORIDE; CISPLATIN; DNA; ESTER; PLATINUM COMPLEX;

EID: 84866338453     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300879k     Document Type: Article
Times cited : (49)

References (35)
  • 1
    • 34547100275 scopus 로고    scopus 로고
    • The resurgence of platinum-based cancer chemotherapy
    • Kelland, L. The resurgence of platinum-based cancer chemotherapy Nature Rev. Cancer 2007, 7, 573-784
    • (2007) Nature Rev. Cancer , vol.7 , pp. 573-784
    • Kelland, L.1
  • 2
    • 77957375221 scopus 로고    scopus 로고
    • Cisplatin resistance: Preclinical findings and clinical implications
    • Koberle, B.; Tomicic, M. T.; Usanova, S.; Kaina, B. Cisplatin resistance: preclinical findings and clinical implications Biochim. Biophys. Acta 2010, 1806, 172-182
    • (2010) Biochim. Biophys. Acta , vol.1806 , pp. 172-182
    • Koberle, B.1    Tomicic, M.T.2    Usanova, S.3    Kaina, B.4
  • 3
    • 0031408767 scopus 로고    scopus 로고
    • Testicular cancer: An oncological success story
    • Einhorn, L. H. Testicular cancer: an oncological success story Clin. Cancer Res. 1997, 3, 2630-2632 (Pubitemid 28133118)
    • (1997) Clinical Cancer Research , vol.3 , Issue.12 , pp. 2630-2632
    • Einhorn, L.H.1
  • 4
    • 0033372348 scopus 로고    scopus 로고
    • Palliative chemotherapy: No longer a contradiction in terms
    • Archer, V. R.; Billingham, L. J.; Cullen, M. H. Palliative chemotherapy: no longer a contradiction in terms Oncologist 1999, 4, 470-477 (Pubitemid 30013181)
    • (1999) Oncologist , vol.4 , Issue.6 , pp. 470-477
    • Archer, V.R.1    Billingham, L.J.2    Cullen, M.H.3
  • 5
    • 40249094603 scopus 로고    scopus 로고
    • ERCC1 protein expression predicts the response of cisplatin-based neoadjuvant chemotherapy in non-small-cell lung cancer
    • DOI 10.1016/j.lungcan.2007.08.025, PII S0169500207004953
    • Fujii, T.; Toyooka, S.; Ichimura, K.; Fujiwara, Y.; Hotta, K.; Soh, J.; Suehisa, H.; Kobayashi, N.; Aoe, M.; Yoshino, T.; Kiura, K. Date, H. ERCC1 protein expression predicts the response of cisplatin-based neoadjuvant chemotherapy in non-small-cell lung cancer Lung Cancer 2008, 59, 377-384 (Pubitemid 351335101)
    • (2008) Lung Cancer , vol.59 , Issue.3 , pp. 377-384
    • Fujii, T.1    Toyooka, S.2    Ichimura, K.3    Fujiwara, Y.4    Hotta, K.5    Soh, J.6    Suehisa, H.7    Kobayashi, N.8    Aoe, M.9    Yoshino, T.10    Kiura, K.11    Date, H.12
  • 8
    • 23844453144 scopus 로고    scopus 로고
    • Novel approaches towards development of non-classical platinum-based antineoplastic agents: Design of platinum complexes characterized by an alternative DNA-binding pattern and/or tumor-targeted cytotoxicity
    • DOI 10.2174/0929867054864877
    • Momekov, G.; Bakalova, A.; Karaivanova, M. Novel approaches towards development of non-classical platinum-based antineoplastic agents: design of platinum complexes characterized by an alternative DNA-binding pattern and/or tumor-targeted cytotoxicity Curr. Med. Chem. 2005, 12, 2177-2191 (Pubitemid 41179706)
    • (2005) Current Medicinal Chemistry , vol.12 , Issue.19 , pp. 2177-2191
    • Momekov, G.1    Bakalova, A.2    Karaivanova, M.3
  • 9
    • 79960169559 scopus 로고    scopus 로고
    • Unique platinum-DNA interactions may lead to more effective platinum-based antitumor drugs
    • Komeda, S. Unique platinum-DNA interactions may lead to more effective platinum-based antitumor drugs Metallomics 2011, 3, 650-655
    • (2011) Metallomics , vol.3 , pp. 650-655
    • Komeda, S.1
  • 10
    • 33846071608 scopus 로고    scopus 로고
    • Adenine-N3 in the DNA minor groove - An emerging target for platinum containing anticancer pharmacophores
    • Guddneppanavar, R.; Bierbach, U. Adenine-N3 in the DNA minor groove-an emerging target for platinum containing anticancer pharmacophores Anticancer Agents Med. Chem. 2007, 7, 125-138 (Pubitemid 46062409)
    • (2007) Anti-Cancer Agents in Medicinal Chemistry , vol.7 , Issue.1 , pp. 125-138
    • Guddneppanavar, R.1    Bierbach, U.2
  • 12
    • 57349182469 scopus 로고    scopus 로고
    • A non-cross-linking platinum-acridine agent with potent activity in non-small-cell lung cancer
    • Ma, Z.; Choudhury, J. R.; Wright, M. W.; Day, C. S.; Saluta, G.; Kucera, G. L.; Bierbach, U. A non-cross-linking platinum-acridine agent with potent activity in non-small-cell lung cancer J. Med. Chem. 2008, 51, 7574-7580
    • (2008) J. Med. Chem. , vol.51 , pp. 7574-7580
    • Ma, Z.1    Choudhury, J.R.2    Wright, M.W.3    Day, C.S.4    Saluta, G.5    Kucera, G.L.6    Bierbach, U.7
  • 13
    • 84863687735 scopus 로고    scopus 로고
    • Analysis of the DNA damage produced by a platinum-acridine antitumor agent and its effects in NCI-H460 lung cancer cells
    • Qiao, X.; Zeitany, A. E.; Wright, M. W.; Essader, A. S.; Levine, K. E.; Kucera, G. L.; Bierbach, U. Analysis of the DNA damage produced by a platinum-acridine antitumor agent and its effects in NCI-H460 lung cancer cells Metallomics 2012, 4, 645-652
    • (2012) Metallomics , vol.4 , pp. 645-652
    • Qiao, X.1    Zeitany, A.E.2    Wright, M.W.3    Essader, A.S.4    Levine, K.E.5    Kucera, G.L.6    Bierbach, U.7
  • 15
    • 80955122676 scopus 로고    scopus 로고
    • Inhibition of DNA Synthesis by a Platinum-Acridine Hybrid Agent Leads to Potent Cell Kill in Non-Small Cell Lung Cancer
    • Smyre, C. L.; Saluta, G.; Kute, T. E.; Kucera, G. L.; Bierbach, U. Inhibition of DNA Synthesis by a Platinum-Acridine Hybrid Agent Leads to Potent Cell Kill in Non-Small Cell Lung Cancer ACS Med. Chem. Lett. 2011, 2, 870-874
    • (2011) ACS Med. Chem. Lett. , vol.2 , pp. 870-874
    • Smyre, C.L.1    Saluta, G.2    Kute, T.E.3    Kucera, G.L.4    Bierbach, U.5
  • 16
    • 77955312203 scopus 로고    scopus 로고
    • Antibody-drug conjugates: Targeted drug delivery for cancer
    • Alley, S. C.; Okeley, N. M.; Senter, P. D. Antibody-drug conjugates: targeted drug delivery for cancer Curr. Opin. Chem. Biol. 2010, 14, 529-537
    • (2010) Curr. Opin. Chem. Biol. , vol.14 , pp. 529-537
    • Alley, S.C.1    Okeley, N.M.2    Senter, P.D.3
  • 17
    • 26044434878 scopus 로고    scopus 로고
    • Synthesis, structure, and reactivity of monofunctional platinum(II) and palladium(II) complexes containing the sterically hindered ligand 6-(methylpyridin-2-yl)acetate
    • DOI 10.1016/j.jinorgbio.2005.06.021, PII S0162013405001844
    • Ma, Y.; Day, C. S.; Bierbach, U. Synthesis, structure, and reactivity of monofunctional platinum(II) and palladium(II) complexes containing the sterically hindered ligand 6-(methylpyridin-2-yl)acetate J. Inorg. Biochem. 2005, 99, 2013-2023 (Pubitemid 41405627)
    • (2005) Journal of Inorganic Biochemistry , vol.99 , Issue.10 , pp. 2013-2023
    • Ma, Y.1    Day, C.S.2    Bierbach, U.3
  • 19
    • 33751391677 scopus 로고
    • Toward artificial metalloproteases: Mechanisms by which platinum(II) and palladium(II) complexes promote selective, fast hydrolysis of unactivated amide bonds in peptides
    • Zhu, L.; Kostic, N. M. Toward artificial metalloproteases: mechanisms by which platinum(II) and palladium(II) complexes promote selective, fast hydrolysis of unactivated amide bonds in peptides Inorg. Chem. 1992, 31, 3994-4001
    • (1992) Inorg. Chem. , vol.31 , pp. 3994-4001
    • Zhu, L.1    Kostic, N.M.2
  • 20
    • 33846095450 scopus 로고    scopus 로고
    • The role of sulfur in platinum anticancer chemotherapy
    • Wang, X.; Guo, Z. The role of sulfur in platinum anticancer chemotherapy Anticancer Agents Med. Chem. 2007, 7, 19-34 (Pubitemid 46062403)
    • (2007) Anti-Cancer Agents in Medicinal Chemistry , vol.7 , Issue.1 , pp. 19-34
    • Wang, X.1    Guo, Z.2
  • 21
    • 0025322746 scopus 로고
    • Biophysical studies of the modification of DNA by antitumour platinum coordination complexes
    • DOI 10.1016/0301-4622(90)80003-P
    • Brabec, V.; Kleinwächter, V.; Butour, J.-L.; Johnson, N. P. Biophysical studies of the modification of DNA by antitumor platinum coordination-complexes Biophys. Chem. 1990, 35, 129-141 (Pubitemid 20185433)
    • (1990) Biophysical Chemistry , vol.35 , Issue.2-3 , pp. 129-141
    • Brabec, V.1    Kleinwachter, V.2    Butour, J.-L.3    Johnson, N.P.4
  • 22
    • 0037099290 scopus 로고    scopus 로고
    • Mechanism of action of non-cisplatin type DNA-targeted platinum anticancer agents: DNA interactions of novel acridinylthioureas and their platinum conjugates
    • DOI 10.1016/S0006-2952(02)01107-3, PII S0006295202011073
    • Baruah, H.; Rector, C. L.; Monnier, S. M.; Bierbach, U. Mechanism of action of non-cisplatin type DNA-targeted platinum anticancer agents: DNA interactions of novel acridinylthioureas and their platinum conjugates Biochem. Pharmacol. 2002, 64, 191-200 (Pubitemid 34775298)
    • (2002) Biochemical Pharmacology , vol.64 , Issue.2 , pp. 191-200
    • Baruah, H.1    Rector, C.L.2    Monnier, S.M.3    Bierbach, U.4
  • 23
    • 27244458221 scopus 로고    scopus 로고
    • Characterization of the bisintercalative DNA binding mode of a bifunctional platinum-acridine agent
    • DOI 10.1093/nar/gki869
    • Choudhury, J. R.; Bierbach, U. Characterization of the bisintercalative DNA binding mode of a bifunctional platinum-acridine agent Nucleic Acids Res. 2005, 33, 5622-5632 (Pubitemid 41548828)
    • (2005) Nucleic Acids Research , vol.33 , Issue.17 , pp. 5622-5632
    • Choudhury, J.R.1    Bierbach, U.2
  • 24
    • 79955804251 scopus 로고    scopus 로고
    • Rates of intercalator-driven platination of DNA determined by a restriction enzyme cleavage inhibition assay
    • Choudhury, J. R.; Rao, L.; Bierbach, U. Rates of intercalator-driven platination of DNA determined by a restriction enzyme cleavage inhibition assay J. Biol. Inorg. Chem. 2011, 16, 373-380
    • (2011) J. Biol. Inorg. Chem. , vol.16 , pp. 373-380
    • Choudhury, J.R.1    Rao, L.2    Bierbach, U.3
  • 26
    • 0026594392 scopus 로고
    • High resistance to cisplatin in human ovarian cancer cell lines is associated with marked increase of glutathione synthesis
    • Godwin, A. K.; Meister, A.; O'Dwyer, P. J.; Huang, C. S.; Hamilton, T. C.; Anderson, M. E. High resistance to cisplatin in human ovarian cancer cell lines is associated with marked increase of glutathione synthesis Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 3070-3074
    • (1992) Proc. Natl. Acad. Sci. U.S.A. , vol.89 , pp. 3070-3074
    • Godwin, A.K.1    Meister, A.2    O'Dwyer, P.J.3    Huang, C.S.4    Hamilton, T.C.5    Anderson, M.E.6
  • 27
    • 34548704127 scopus 로고    scopus 로고
    • Enhancing cisplatin sensitivity in MCF-7 human breast cancer cells by down-regulation of Bcl-2 and cyclin D1
    • Yde, C. W.; Issinger, O. G. Enhancing cisplatin sensitivity in MCF-7 human breast cancer cells by down-regulation of Bcl-2 and cyclin D1 Int. J. Oncol. 2006, 29, 1397-1404
    • (2006) Int. J. Oncol. , vol.29 , pp. 1397-1404
    • Yde, C.W.1    Issinger, O.G.2
  • 28
    • 67650485895 scopus 로고    scopus 로고
    • Gemcitabine-based chemogene therapy for pancreatic cancer using Ad-dCK::UMK GDEPT and TS/RR siRNA strategies
    • Rejiba, S.; Bigand, C.; Parmentier, C.; Hajri, A. Gemcitabine-based chemogene therapy for pancreatic cancer using Ad-dCK::UMK GDEPT and TS/RR siRNA strategies Neoplasia 2009, 11, 637-650
    • (2009) Neoplasia , vol.11 , pp. 637-650
    • Rejiba, S.1    Bigand, C.2    Parmentier, C.3    Hajri, A.4
  • 29
    • 23044492007 scopus 로고    scopus 로고
    • Role of checkpoint kinase 1 in preventing premature mitosis in response to gemcitabine
    • DOI 10.1158/0008-5472.CAN-04-2246
    • Morgan, M. A.; Parsels, L. A.; Parsels, J. D.; Mesiwala, A. K.; Maybaum, J.; Lawrence, T. S. Role of checkpoint kinase 1 in preventing premature mitosis in response to gemcitabine Cancer Res. 2005, 65, 6835-6842 (Pubitemid 41060722)
    • (2005) Cancer Research , vol.65 , Issue.15 , pp. 6835-6842
    • Morgan, M.A.1    Parsels, L.A.2    Parsels, J.D.3    Mesiwala, A.K.4    Maybaum, J.5    Lawrence, T.S.6
  • 31
    • 0002950838 scopus 로고    scopus 로고
    • Anticancer activity of cisplatin and related complexes
    • In; Clarke, M. J. Sadler, P. J. Springer: New York
    • Gelasco, A.; Lippard, S. J. Anticancer activity of cisplatin and related complexes. In Topics in Biological Inorganic Chemistry; Clarke, M. J.; Sadler, P. J., Eds.; Springer: New York, 1999; pp 1-43.
    • (1999) Topics in Biological Inorganic Chemistry , pp. 1-43
    • Gelasco, A.1    Lippard, S.J.2
  • 33
    • 0037430653 scopus 로고    scopus 로고
    • Bis(acridinylthiourea)platinum(II) complexes: Synthesis, DNA affinity, and biological activity in glioblastoma cells
    • DOI 10.1016/S0960-894X(02)01078-8
    • Augustus, T. M.; Anderson, J.; Hess, S. M.; Bierbach, U. Bis(acridinylthiourea)platinum(II) complexes: synthesis, DNA affinity, and biological activity in glioblastoma cells Bioorg. Med. Chem. Lett. 2003, 13, 855-858 (Pubitemid 36255553)
    • (2003) Bioorganic and Medicinal Chemistry Letters , vol.13 , Issue.5 , pp. 855-858
    • Augustus, T.M.1    Anderson, J.2    Hess, S.M.3    Bierbach, U.4
  • 34
    • 0035818902 scopus 로고    scopus 로고
    • Design, synthesis, and biological activity of a novel non-cisplatin-type platinum-acridine pharmacophore
    • DOI 10.1021/jm010293m
    • Martins, E. T.; Baruah, H.; Kramarczyk, J.; Saluta, G.; Day, C. S.; Kucera, G. L.; Bierbach, U. Design, synthesis, and biological activity of a novel non-cisplatin-type platinum-acridine pharmacophore J. Med. Chem. 2001, 44, 4492-4496 (Pubitemid 33138136)
    • (2001) Journal of Medicinal Chemistry , vol.44 , Issue.25 , pp. 4492-4496
    • Martins, E.T.1    Baruah, H.2    Kramarczyk, J.3    Saluta, G.4    Day, C.S.5    Kucera, G.L.6    Bierbach, U.7
  • 35
    • 0017279437 scopus 로고
    • Electrophoretic analysis of covalently closed SV40 DNA: Boltzmann distributions of DNA species
    • DeLeys, R. J.; Jackson, D. A. Electrophoretic analysis of covalently closed SV40 DNA: Boltzmann distributions of DNA species Nucleic Acids Res. 1976, 3, 641-652
    • (1976) Nucleic Acids Res. , vol.3 , pp. 641-652
    • Deleys, R.J.1    Jackson, D.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.