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Volumn 57, Issue 21, 2014, Pages 8936-8946

Coordination of hydroxyquinolines to a ruthenium bis-dimethyl-phenanthroline scaffold radically improves potency for potential as antineoplastic agents

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; QUINOLINOL DERIVATIVE; RUTHENIUM BIS DIMETHYL PHENANTHROLINE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG; CLIOQUINOL; COORDINATION COMPOUND; COPPER; CUPRIC CHLORIDE; PROTEASOME INHIBITOR; QUINOLINE DERIVATIVE; RUTHENIUM;

EID: 84923832140     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm501043s     Document Type: Article
Times cited : (84)

References (42)
  • 1
    • 84896508103 scopus 로고    scopus 로고
    • Clioquinol promotes the degradation of metal-dependent amyloid-beta (Abeta) oligomers to restore endocytosis and ameliorate Abeta toxicity
    • Matlack, K. E.; Tardiff, D. F.; Narayan, P.; Hamamichi, S.; Caldwell, K. A.; Caldwell, G. A.; Lindquist, S. Clioquinol promotes the degradation of metal-dependent amyloid-beta (Abeta) oligomers to restore endocytosis and ameliorate Abeta toxicity Proc. Natl. Acad. Sci. U. S. A. 2014, 111 (11) 4013-4018
    • (2014) Proc. Natl. Acad. Sci. U. S. A. , vol.111 , Issue.11 , pp. 4013-4018
    • Matlack, K.E.1    Tardiff, D.F.2    Narayan, P.3    Hamamichi, S.4    Caldwell, K.A.5    Caldwell, G.A.6    Lindquist, S.7
  • 3
    • 84856280358 scopus 로고    scopus 로고
    • Clioquinol: Review of its mechanisms of action and clinical uses in neurodegenerative disorders
    • Bareggi, S. R.; Cornelli, U. Clioquinol: review of its mechanisms of action and clinical uses in neurodegenerative disorders CNS Neurosci. Ther. 2011, 18 (1) 41-46
    • (2011) CNS Neurosci. Ther. , vol.18 , Issue.1 , pp. 41-46
    • Bareggi, S.R.1    Cornelli, U.2
  • 4
    • 0038705203 scopus 로고    scopus 로고
    • Hydroxyquinolines as iron chelators
    • Pierre, J. L.; Baret, P.; Serratrice, G. Hydroxyquinolines as iron chelators Curr. Med. Chem. 2003, 10 (12) 1077-1084
    • (2003) Curr. Med. Chem. , vol.10 , Issue.12 , pp. 1077-1084
    • Pierre, J.L.1    Baret, P.2    Serratrice, G.3
  • 5
    • 17144404213 scopus 로고    scopus 로고
    • Anticancer activity of the antibiotic clioquinol
    • Ding, W. Q.; Liu, B.; Vaught, J. L.; Yamauchi, H.; Lind, S. E. Anticancer activity of the antibiotic clioquinol Cancer Res. 2005, 65 (8) 3389-3395
    • (2005) Cancer Res. , vol.65 , Issue.8 , pp. 3389-3395
    • Ding, W.Q.1    Liu, B.2    Vaught, J.L.3    Yamauchi, H.4    Lind, S.E.5
  • 6
    • 79961200410 scopus 로고    scopus 로고
    • High-Efficiency Tris(8-hydroxyquinoline)aluminum (Alq(3)) Complexes for Organic White-Light-Emitting Diodes and Solid-State Lighting
    • Perez-Bolivar, C.; Takizawa, S. Y.; Nishimura, G.; Montes, V. A.; Anzenbacher, P. High-Efficiency Tris(8-hydroxyquinoline)aluminum (Alq(3)) Complexes for Organic White-Light-Emitting Diodes and Solid-State Lighting Chem.-Eur. J. 2011, 17 (33) 9076-9082
    • (2011) Chem.-Eur. J. , vol.17 , Issue.33 , pp. 9076-9082
    • Perez-Bolivar, C.1    Takizawa, S.Y.2    Nishimura, G.3    Montes, V.A.4    Anzenbacher, P.5
  • 7
    • 0001173320 scopus 로고    scopus 로고
    • Ground-state properties and excited-state reactivity of 8-quinolate complexes of ruthenium(II)
    • Warren, J. T.; Chen, W.; Johnston, D. H.; Turro, C. Ground-state properties and excited-state reactivity of 8-quinolate complexes of ruthenium(II) Inorg. Chem. 1999, 38 (26) 6187-6192
    • (1999) Inorg. Chem. , vol.38 , Issue.26 , pp. 6187-6192
    • Warren, J.T.1    Chen, W.2    Johnston, D.H.3    Turro, C.4
  • 8
    • 78649637528 scopus 로고    scopus 로고
    • Electronic tuning of ruthenium complexes by 8-quinolate ligands
    • Sears, R. B.; Joyce, L. E.; Turro, C. Electronic tuning of ruthenium complexes by 8-quinolate ligands Photochem. Photobiol. 2010, 86 (6) 1230-1236
    • (2010) Photochem. Photobiol. , vol.86 , Issue.6 , pp. 1230-1236
    • Sears, R.B.1    Joyce, L.E.2    Turro, C.3
  • 9
    • 77449146289 scopus 로고    scopus 로고
    • Metal ionophores-an emerging class of anticancer drugs
    • Ding, W. Q.; Lind, S. E. Metal ionophores-an emerging class of anticancer drugs IUBMB Life 2009, 61 (11) 1013-1018
    • (2009) IUBMB Life , vol.61 , Issue.11 , pp. 1013-1018
    • Ding, W.Q.1    Lind, S.E.2
  • 10
    • 84871031059 scopus 로고    scopus 로고
    • Copper-dependent cytotoxicity of 8-hydroxyquinoline derivatives correlates with their hydrophobicity and does not require caspase activation
    • Tardito, S.; Barilli, A.; Bassanetti, I.; Tegoni, M.; Bussolati, O.; Franchi-Gazzola, R.; Mucchino, C.; Marchio, L. Copper-dependent cytotoxicity of 8-hydroxyquinoline derivatives correlates with their hydrophobicity and does not require caspase activation J. Med. Chem. 2012, 55 (23) 10448-10459
    • (2012) J. Med. Chem. , vol.55 , Issue.23 , pp. 10448-10459
    • Tardito, S.1    Barilli, A.2    Bassanetti, I.3    Tegoni, M.4    Bussolati, O.5    Franchi-Gazzola, R.6    Mucchino, C.7    Marchio, L.8
  • 11
    • 77949267166 scopus 로고    scopus 로고
    • Tumor cellular proteasome inhibition and growth suppression by 8-hydroxyquinoline and clioquinol requires their capabilities to bind copper and transport copper into cells
    • Zhai, S.; Yang, L.; Cui, Q. C.; Sun, Y.; Dou, Q. P.; Yan, B. Tumor cellular proteasome inhibition and growth suppression by 8-hydroxyquinoline and clioquinol requires their capabilities to bind copper and transport copper into cells J. Biol. Inorg. Chem. 2010, 15 (2) 259-269
    • (2010) J. Biol. Inorg. Chem. , vol.15 , Issue.2 , pp. 259-269
    • Zhai, S.1    Yang, L.2    Cui, Q.C.3    Sun, Y.4    Dou, Q.P.5    Yan, B.6
  • 13
    • 78751661570 scopus 로고    scopus 로고
    • Identifying chelators for metalloprotein inhibitors using a fragment-based approach
    • Jacobsen, J. A.; Fullagar, J. L.; Miller, M. T.; Cohen, S. M. Identifying chelators for metalloprotein inhibitors using a fragment-based approach J. Med. Chem. 2011, 54 (2) 591-602
    • (2011) J. Med. Chem. , vol.54 , Issue.2 , pp. 591-602
    • Jacobsen, J.A.1    Fullagar, J.L.2    Miller, M.T.3    Cohen, S.M.4
  • 14
    • 75649105423 scopus 로고    scopus 로고
    • A prochelator activated by hydrogen peroxide prevents metal-induced amyloid Beta aggregation
    • Dickens, M. G.; Franz, K. J. A prochelator activated by hydrogen peroxide prevents metal-induced amyloid Beta aggregation ChemBioChem 2010, 11 (1) 59-62
    • (2010) ChemBioChem , vol.11 , Issue.1 , pp. 59-62
    • Dickens, M.G.1    Franz, K.J.2
  • 15
    • 77149144132 scopus 로고    scopus 로고
    • Minding metals: Tailoring multifunctional chelating agents for neurodegenerative disease
    • Perez, L. R.; Franz, K. J. Minding metals: tailoring multifunctional chelating agents for neurodegenerative disease Dalton Trans 2010, 39 (9) 2177-2187
    • (2010) Dalton Trans , vol.39 , Issue.9 , pp. 2177-2187
    • Perez, L.R.1    Franz, K.J.2
  • 16
    • 84861395922 scopus 로고    scopus 로고
    • Strained ruthenium complexes are potent light-activated anticancer agents
    • Howerton, B. S.; Heidary, D. K.; Glazer, E. C. Strained ruthenium complexes are potent light-activated anticancer agents J. Am. Chem. Soc. 2012, 134 (20) 8324-8327
    • (2012) J. Am. Chem. Soc. , vol.134 , Issue.20 , pp. 8324-8327
    • Howerton, B.S.1    Heidary, D.K.2    Glazer, E.C.3
  • 17
    • 84865677118 scopus 로고    scopus 로고
    • Light-activated ruthenium complexes photobind DNA and are cytotoxic in the photodynamic therapy window
    • Wachter, E.; Heidary, D. K.; Howerton, B. S.; Parkin, S.; Glazer, E. C. Light-activated ruthenium complexes photobind DNA and are cytotoxic in the photodynamic therapy window Chem. Commun. 2012, 48 (77) 9649-9651
    • (2012) Chem. Commun. , vol.48 , Issue.77 , pp. 9649-9651
    • Wachter, E.1    Heidary, D.K.2    Howerton, B.S.3    Parkin, S.4    Glazer, E.C.5
  • 19
    • 60549103259 scopus 로고    scopus 로고
    • Spheroid-based drug screen: Considerations and practical approach
    • Friedrich, J.; Seidel, C.; Ebner, R.; Kunz-Schughart, L. A. Spheroid-based drug screen: considerations and practical approach Nature Protoc. 2009, 4 (3) 309-324
    • (2009) Nature Protoc. , vol.4 , Issue.3 , pp. 309-324
    • Friedrich, J.1    Seidel, C.2    Ebner, R.3    Kunz-Schughart, L.A.4
  • 20
    • 16544380146 scopus 로고    scopus 로고
    • The use of 3-D cultures for high-throughput screening: The multicellular spheroid model
    • Kunz-Schughart, L. A.; Freyer, J. P.; Hofstaedter, F.; Ebner, R. The use of 3-D cultures for high-throughput screening: the multicellular spheroid model J. Biomol. Screening 2004, 9 (4) 273-285
    • (2004) J. Biomol. Screening , vol.9 , Issue.4 , pp. 273-285
    • Kunz-Schughart, L.A.1    Freyer, J.P.2    Hofstaedter, F.3    Ebner, R.4
  • 21
    • 37749053847 scopus 로고    scopus 로고
    • Screening for compounds that induce apoptosis of cancer cells grown as multicellular spheroids
    • Herrmann, R.; Fayad, W.; Schwarz, S.; Berndtsson, M.; Linder, S. Screening for compounds that induce apoptosis of cancer cells grown as multicellular spheroids J. Biomol. Screening 2008, 13 (1) 1-8
    • (2008) J. Biomol. Screening , vol.13 , Issue.1 , pp. 1-8
    • Herrmann, R.1    Fayad, W.2    Schwarz, S.3    Berndtsson, M.4    Linder, S.5
  • 23
    • 84871940845 scopus 로고    scopus 로고
    • Development of proteasome inhibitors as research tools and cancer drugs
    • Goldberg, A. L. Development of proteasome inhibitors as research tools and cancer drugs J. Cell Biol. 2012, 199 (4) 583-588
    • (2012) J. Cell Biol. , vol.199 , Issue.4 , pp. 583-588
    • Goldberg, A.L.1
  • 24
    • 0032971227 scopus 로고    scopus 로고
    • Degradation of cell proteins and the generation of MHC class I-presented peptides
    • Rock, K. L.; Goldberg, A. L. Degradation of cell proteins and the generation of MHC class I-presented peptides Annu. Rev. Immunol. 1999, 17, 739-779
    • (1999) Annu. Rev. Immunol. , vol.17 , pp. 739-779
    • Rock, K.L.1    Goldberg, A.L.2
  • 25
    • 0027980319 scopus 로고
    • Inhibitors of the proteasome block the degradation of most cell proteins and the generation of peptides presented on MHC class i molecules
    • Rock, K. L.; Gramm, C.; Rothstein, L.; Clark, K.; Stein, R.; Dick, L.; Hwang, D.; Goldberg, A. L. Inhibitors of the proteasome block the degradation of most cell proteins and the generation of peptides presented on MHC class I molecules Cell 1994, 78 (5) 761-771
    • (1994) Cell , vol.78 , Issue.5 , pp. 761-771
    • Rock, K.L.1    Gramm, C.2    Rothstein, L.3    Clark, K.4    Stein, R.5    Dick, L.6    Hwang, D.7    Goldberg, A.L.8
  • 26
    • 1542270307 scopus 로고    scopus 로고
    • Organic copper complexes as a new class of proteasome inhibitors and apoptosis inducers in human cancer cells
    • Daniel, K. G.; Gupta, P.; Harbach, R. H.; Guida, W. C.; Dou, Q. P. Organic copper complexes as a new class of proteasome inhibitors and apoptosis inducers in human cancer cells Biochem. Pharmacol. 2004, 67 (6) 1139-1151
    • (2004) Biochem. Pharmacol. , vol.67 , Issue.6 , pp. 1139-1151
    • Daniel, K.G.1    Gupta, P.2    Harbach, R.H.3    Guida, W.C.4    Dou, Q.P.5
  • 28
    • 79951717280 scopus 로고    scopus 로고
    • Clioquinol-a novel copper-dependent and independent proteasome inhibitor
    • Schimmer, A. D. Clioquinol-a novel copper-dependent and independent proteasome inhibitor Curr. Cancer Drug Targets 2011, 11 (3) 325-331
    • (2011) Curr. Cancer Drug Targets , vol.11 , Issue.3 , pp. 325-331
    • Schimmer, A.D.1
  • 29
    • 0037366133 scopus 로고    scopus 로고
    • Biochemical modulation of cisplatin mechanisms of action: Enhancement of antitumor activity and circumvention of drug resistance
    • Fuertes, M. A.; Alonso, C.; Perez, J. M. Biochemical modulation of cisplatin mechanisms of action: enhancement of antitumor activity and circumvention of drug resistance Chem. Rev. 2003, 103 (3) 645-662
    • (2003) Chem. Rev. , vol.103 , Issue.3 , pp. 645-662
    • Fuertes, M.A.1    Alonso, C.2    Perez, J.M.3
  • 30
    • 84901648175 scopus 로고    scopus 로고
    • Clioquinol and pyrrolidine dithiocarbamate complex with copper to form proteasome inhibitors and apoptosis inducers in human breast cancer cells
    • Daniel, K. G.; Chen, D.; Orlu, S.; Cui, Q. C.; Miller, F. R.; Dou, Q. P. Clioquinol and pyrrolidine dithiocarbamate complex with copper to form proteasome inhibitors and apoptosis inducers in human breast cancer cells Breast Cancer Res. 2005, 7 (6) R897-R908
    • (2005) Breast Cancer Res. , vol.7 , Issue.6 , pp. 897-R908
    • Daniel, K.G.1    Chen, D.2    Orlu, S.3    Cui, Q.C.4    Miller, F.R.5    Dou, Q.P.6
  • 31
    • 33847746963 scopus 로고    scopus 로고
    • Clioquinol, a therapeutic agent for Alzheimers disease, has proteasome-inhibitory, androgen receptor-suppressing, apoptosis-inducing, and antitumor activities in human prostate cancer cells and xenografts
    • Chen, D.; Cui, Q. C.; Yang, H.; Barrea, R. A.; Sarkar, F. H.; Sheng, S.; Yan, B.; Reddy, G. P.; Dou, Q. P. Clioquinol, a therapeutic agent for Alzheimers disease, has proteasome-inhibitory, androgen receptor-suppressing, apoptosis-inducing, and antitumor activities in human prostate cancer cells and xenografts Cancer Res. 2007, 67 (4) 1636-1644
    • (2007) Cancer Res. , vol.67 , Issue.4 , pp. 1636-1644
    • Chen, D.1    Cui, Q.C.2    Yang, H.3    Barrea, R.A.4    Sarkar, F.H.5    Sheng, S.6    Yan, B.7    Reddy, G.P.8    Dou, Q.P.9
  • 32
    • 84881499406 scopus 로고    scopus 로고
    • A genome-wide siRNA screen identifies proteasome addiction as a vulnerability of basal-like triple-negative breast cancer cells
    • Petrocca, F.; Altschuler, G.; Tan, S. M.; Mendillo, M. L.; Yan, H.; Jerry, D. J.; Kung, A. L.; Hide, W.; Ince, T. A.; Lieberman, J. A genome-wide siRNA screen identifies proteasome addiction as a vulnerability of basal-like triple-negative breast cancer cells Cancer Cell 2013, 24 (2) 182-196
    • (2013) Cancer Cell , vol.24 , Issue.2 , pp. 182-196
    • Petrocca, F.1    Altschuler, G.2    Tan, S.M.3    Mendillo, M.L.4    Yan, H.5    Jerry, D.J.6    Kung, A.L.7    Hide, W.8    Ince, T.A.9    Lieberman, J.10
  • 34
    • 84870723725 scopus 로고    scopus 로고
    • Synthesis, crystal structure, cytotoxicity and DNA interaction of 5,7-dichloro-8-quinolinolato-lanthanides
    • Chen, Z. F.; Gu, Y. Q.; Song, X. Y.; Liu, Y. C.; Peng, Y.; Liang, H. Synthesis, crystal structure, cytotoxicity and DNA interaction of 5,7-dichloro-8-quinolinolato-lanthanides Eur. J. Med. Chem. 2013, 59, 194-202
    • (2013) Eur. J. Med. Chem. , vol.59 , pp. 194-202
    • Chen, Z.F.1    Gu, Y.Q.2    Song, X.Y.3    Liu, Y.C.4    Peng, Y.5    Liang, H.6
  • 35
    • 84896736882 scopus 로고    scopus 로고
    • A light-activated metal complex targets both DNA and RNA in a fluorescent in vitro transcription and translation assay
    • Heidary, D. K.; Glazer, E. C. A light-activated metal complex targets both DNA and RNA in a fluorescent in vitro transcription and translation assay ChemBioChem 2014, 15 (4) 507-511
    • (2014) ChemBioChem , vol.15 , Issue.4 , pp. 507-511
    • Heidary, D.K.1    Glazer, E.C.2
  • 36
    • 0016737869 scopus 로고
    • The mechanism of inhibition of ribonucleic acid synthesis by 8-hydroxyquinoline and the antibiotic lomofungin
    • While it has been reported that 8-hydroxyquinoline inhibited RNA synthesis, this occurred at mM concentrations, well above the concentration used in our assay. See; ()
    • While it has been reported that 8-hydroxyquinoline inhibited RNA synthesis, this occurred at mM concentrations, well above the concentration used in our assay. See Fraser, R. S.; Creanor, J. The mechanism of inhibition of ribonucleic acid synthesis by 8-hydroxyquinoline and the antibiotic lomofungin Biochem. J. 1975, 147 (3) 401-410
    • (1975) Biochem. J. , vol.147 , Issue.3 , pp. 401-410
    • Fraser, R.S.1    Creanor, J.2
  • 37
    • 84901664160 scopus 로고    scopus 로고
    • Structural characterization and biological evaluation of a clioquinol-ruthenium complex with copper-independent antileukaemic activity
    • Gobec, M.; Kljun, J.; Sosic, I.; Mlinaric-Rascan, I.; Ursic, M.; Gobec, S.; Turel, I. Structural characterization and biological evaluation of a clioquinol-ruthenium complex with copper-independent antileukaemic activity Dalton Trans 2014, 43 (24) 9045-9051
    • (2014) Dalton Trans , vol.43 , Issue.24 , pp. 9045-9051
    • Gobec, M.1    Kljun, J.2    Sosic, I.3    Mlinaric-Rascan, I.4    Ursic, M.5    Gobec, S.6    Turel, I.7
  • 40
    • 84896811855 scopus 로고    scopus 로고
    • Interaction between 8-hydroxyquinoline ruthenium(II) complexes and basic fibroblast growth factors (bFGF): Inhibiting angiogenesis and tumor growth through ERK and AKT signaling pathways
    • Yang, L.; Zhang, J.; Wang, C.; Qin, X.; Yu, Q.; Zhou, Y.; Liu, J. Interaction between 8-hydroxyquinoline ruthenium(II) complexes and basic fibroblast growth factors (bFGF): inhibiting angiogenesis and tumor growth through ERK and AKT signaling pathways Metallomics 2014, 6 (3) 518-531
    • (2014) Metallomics , vol.6 , Issue.3 , pp. 518-531
    • Yang, L.1    Zhang, J.2    Wang, C.3    Qin, X.4    Yu, Q.5    Zhou, Y.6    Liu, J.7
  • 41
    • 84881186678 scopus 로고    scopus 로고
    • New uses for old drugs: Attempts to convert quinolone antibacterials into potential anticancer agents containing ruthenium
    • Kljun, J.; Bratsos, I.; Alessio, E.; Psomas, G.; Repnik, U.; Butinar, M.; Turk, B.; Turel, I. New uses for old drugs: attempts to convert quinolone antibacterials into potential anticancer agents containing ruthenium Inorg. Chem. 2013, 52 (15) 9039-9052
    • (2013) Inorg. Chem. , vol.52 , Issue.15 , pp. 9039-9052
    • Kljun, J.1    Bratsos, I.2    Alessio, E.3    Psomas, G.4    Repnik, U.5    Butinar, M.6    Turk, B.7    Turel, I.8
  • 42
    • 71549145298 scopus 로고    scopus 로고
    • Anticancer activity of heteroleptic diimine complexes of dirhodium: A study of intercalating properties, hydrophobicity and in cellulo activity
    • Aguirre, J. D.; Angeles-Boza, A. M.; Chouai, A.; Turro, C.; Pellois, J. P.; Dunbar, K. R. Anticancer activity of heteroleptic diimine complexes of dirhodium: a study of intercalating properties, hydrophobicity and in cellulo activity Dalton Trans 2009, 48) 10806-10812
    • (2009) Dalton Trans , Issue.48 , pp. 10806-10812
    • Aguirre, J.D.1    Angeles-Boza, A.M.2    Chouai, A.3    Turro, C.4    Pellois, J.P.5    Dunbar, K.R.6


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