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Volumn 57, Issue 14, 2014, Pages 6043-6059

Discovery and investigation of anticancer ruthenium-arene Schiff-base complexes via water-promoted combinatorial three-component assembly

Author keywords

[No Author keywords available]

Indexed keywords

2 QUINOLINYLMETHYLENE 4 AMINOPHENOL; 4 METHOXY N (2 QUINOLINYLMETHYLENE)ANILINE; ANTINEOPLASTIC AGENT; N (2 PYRIDYLMETHYLENE) 1 NAPHTHYLAMINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROTEIN P53; RUTHENIUM DERIVATIVE; SCHIFF BASE; UNCLASSIFIED DRUG;

EID: 84904977324     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm500455p     Document Type: Article
Times cited : (139)

References (62)
  • 1
    • 11144341956 scopus 로고    scopus 로고
    • Chemical Space and Biology
    • Dobson, C. M. Chemical Space and Biology Nature 2004, 432, 824-828
    • (2004) Nature , vol.432 , pp. 824-828
    • Dobson, C.M.1
  • 2
    • 11144320699 scopus 로고    scopus 로고
    • Navigating Chemical Space for Biology and Medicine
    • Lipinski, C.; Hopkins, A. Navigating Chemical Space for Biology and Medicine Nature 2004, 432, 855-861
    • (2004) Nature , vol.432 , pp. 855-861
    • Lipinski, C.1    Hopkins, A.2
  • 5
    • 0029894013 scopus 로고    scopus 로고
    • The Properties of Known Drugs. 1. Molecular Frameworks
    • Bemis, G. W.; Murcko, M. A. The Properties of Known Drugs. 1. Molecular Frameworks J. Med. Chem. 1996, 39, 2887-2893
    • (1996) J. Med. Chem. , vol.39 , pp. 2887-2893
    • Bemis, G.W.1    Murcko, M.A.2
  • 6
    • 61849162674 scopus 로고    scopus 로고
    • Targeting Proteins with Metal Complexes
    • Meggers, E. Targeting Proteins with Metal Complexes Chem. Commun. 2009, 9, 1001-1010
    • (2009) Chem. Commun. , vol.9 , pp. 1001-1010
    • Meggers, E.1
  • 8
    • 34547100275 scopus 로고    scopus 로고
    • The Resurgence of Platinum-based Cancer Chemotherapy
    • Kelland, L. The Resurgence of Platinum-based Cancer Chemotherapy Nat. Rev. Cancer 2007, 7, 573-584
    • (2007) Nat. Rev. Cancer , vol.7 , pp. 573-584
    • Kelland, L.1
  • 9
    • 33646956829 scopus 로고    scopus 로고
    • Non-Platinum Chemotherapeutic Metallopharmaceuticals
    • Clarke, M. J.; Zhu, F.; Frasca, D. R. Non-Platinum Chemotherapeutic Metallopharmaceuticals Chem. Rev. 1999, 99, 2511-2533
    • (1999) Chem. Rev. , vol.99 , pp. 2511-2533
    • Clarke, M.J.1    Zhu, F.2    Frasca, D.R.3
  • 10
    • 2542625358 scopus 로고    scopus 로고
    • Phase i and Pharmacological Study with Imidazolium- trans -DMSO-imidazole-tetrachlororuthenate, a Novel Ruthenium Anticancer Agent
    • Rademaker-Lakhai, J. M.; van den Bongard, D.; Pluim, D.; Beijnen, J. H.; Schellens, J. H. M. Phase I and Pharmacological Study with Imidazolium- trans -DMSO-imidazole-tetrachlororuthenate, a Novel Ruthenium Anticancer Agent Clin. Cancer Res. 2004, 10, 3717-3727
    • (2004) Clin. Cancer Res. , vol.10 , pp. 3717-3727
    • Rademaker-Lakhai, J.M.1    Van Den Bongard, D.2    Pluim, D.3    Beijnen, J.H.4    Schellens, J.H.M.5
  • 12
    • 84865464514 scopus 로고    scopus 로고
    • Challenges and Opportunities in the Development of Organometallic Anticancer Drugs
    • Hartinger, C. G.; Metzler-Nolte, N.; Dyson, P. J. Challenges and Opportunities in the Development of Organometallic Anticancer Drugs Organometallics 2012, 31, 5677-5685
    • (2012) Organometallics , vol.31 , pp. 5677-5685
    • Hartinger, C.G.1    Metzler-Nolte, N.2    Dyson, P.J.3
  • 13
    • 55449107748 scopus 로고    scopus 로고
    • Medicinal Organometallic Chemistry: Designing Metal Arene Complexes as Anticancer Agents
    • Peacock, A. F.; Sadler, P. J. Medicinal Organometallic Chemistry: Designing Metal Arene Complexes as Anticancer Agents Chem.-Asian J. 2008, 3, 1890-1899
    • (2008) Chem.-Asian J. , vol.3 , pp. 1890-1899
    • Peacock, A.F.1    Sadler, P.J.2
  • 15
    • 84873919075 scopus 로고    scopus 로고
    • The Contrasting Activity of Iodido Versus Chlorido Ruthenium and Osmium Arene Azo- and Imino-pyridine Anticancer Complexes: Control of Cell Selectivity, Cross-Resistance, p53 Dependence, and Apoptosis Pathway
    • Romero-Canelon, I.; Salassa, L.; Sadler, P. J. The Contrasting Activity of Iodido Versus Chlorido Ruthenium and Osmium Arene Azo- and Imino-pyridine Anticancer Complexes: Control of Cell Selectivity, Cross-Resistance, p53 Dependence, and Apoptosis Pathway J. Med. Chem. 2013, 56, 1291-1300
    • (2013) J. Med. Chem. , vol.56 , pp. 1291-1300
    • Romero-Canelon, I.1    Salassa, L.2    Sadler, P.J.3
  • 16
    • 84893761654 scopus 로고    scopus 로고
    • Opening the Lid on Piano-Stool Complexes: An Account of Ruthenium(II)-Arene Complexes with Medicinal Applications
    • Nazarov, A. A.; Hartinger, C. G.; Dyson, P. J. Opening the Lid on Piano-Stool Complexes: An Account of Ruthenium(II)-Arene Complexes with Medicinal Applications J. Organomet. Chem. 2014, 751, 251-260
    • (2014) J. Organomet. Chem. , vol.751 , pp. 251-260
    • Nazarov, A.A.1    Hartinger, C.G.2    Dyson, P.J.3
  • 18
    • 84869409318 scopus 로고    scopus 로고
    • Rational Design of Selective Organoruthenium Inhibitors of Protein Tyrosine Phosphatase 1B
    • Ong, J. X.; Yap, C. W.; Ang, W. H. Rational Design of Selective Organoruthenium Inhibitors of Protein Tyrosine Phosphatase 1B Inorg. Chem. 2012, 51, 12483-12492
    • (2012) Inorg. Chem. , vol.51 , pp. 12483-12492
    • Ong, J.X.1    Yap, C.W.2    Ang, W.H.3
  • 20
    • 79952186235 scopus 로고    scopus 로고
    • Organometallic Ruthenium-Based Antitumor Compounds with Novel Modes of Action
    • Ang, W. H.; Casini, A.; Sava, G.; Dyson, P. J. Organometallic Ruthenium-Based Antitumor Compounds with Novel Modes of Action J. Organomet. Chem. 2011, 696, 989-998
    • (2011) J. Organomet. Chem. , vol.696 , pp. 989-998
    • Ang, W.H.1    Casini, A.2    Sava, G.3    Dyson, P.J.4
  • 21
    • 70449687713 scopus 로고    scopus 로고
    • In Vivo Tumour and Metastasis Reduction and in Vitro Effects on Invasion Assays of the Ruthenium RM175 and Osmium AFAP51 Organometallics in the Mammary Cancer Model
    • Bergamo, A.; Masi, A.; Peacock, A. F.; Habtemariam, A.; Sadler, P. J.; Sava, G. In Vivo Tumour and Metastasis Reduction and in Vitro Effects on Invasion Assays of the Ruthenium RM175 and Osmium AFAP51 Organometallics in the Mammary Cancer Model J. Inorg. Biochem. 2010, 104, 79-86
    • (2010) J. Inorg. Biochem. , vol.104 , pp. 79-86
    • Bergamo, A.1    Masi, A.2    Peacock, A.F.3    Habtemariam, A.4    Sadler, P.J.5    Sava, G.6
  • 23
    • 0035910597 scopus 로고    scopus 로고
    • Combinatorial and Evolution-Based Methods in the Creation of Enantioselective Catalysts
    • Reetz, M. T. Combinatorial and Evolution-Based Methods in the Creation of Enantioselective Catalysts Angew. Chem., Int. Ed. 2001, 40, 284-310
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 284-310
    • Reetz, M.T.1
  • 24
    • 0032088271 scopus 로고    scopus 로고
    • Combinatorial Libraries of Transition-Metal Complexes, Catalysts and Materials
    • Francis, M. B.; Jamison, T. F.; Jacobsen, E. N. Combinatorial Libraries of Transition-Metal Complexes, Catalysts and Materials Curr. Opin. Chem. Biol. 1998, 2, 422-428
    • (1998) Curr. Opin. Chem. Biol. , vol.2 , pp. 422-428
    • Francis, M.B.1    Jamison, T.F.2    Jacobsen, E.N.3
  • 25
    • 77955933614 scopus 로고    scopus 로고
    • Discovery of a Strongly Apoptotic Ruthenium Complex Through Combinatorial Coordination Chemistry
    • Mulcahy, S. P.; Grundler, K.; Frias, C.; Wagner, L.; Prokop, A.; Meggers, E. Discovery of a Strongly Apoptotic Ruthenium Complex Through Combinatorial Coordination Chemistry Dalton Trans. 2010, 39, 8177-8182
    • (2010) Dalton Trans. , vol.39 , pp. 8177-8182
    • Mulcahy, S.P.1    Grundler, K.2    Frias, C.3    Wagner, L.4    Prokop, A.5    Meggers, E.6
  • 28
    • 84887116242 scopus 로고    scopus 로고
    • Synthesis of Ferrocenyl and Ruthenocenyl Thioamide Derivatives Using a Single-Step Three-Component Reaction
    • Patra, M.; Hess, J.; Konatschnig, S.; Spingler, B.; Gasser, G. Synthesis of Ferrocenyl and Ruthenocenyl Thioamide Derivatives Using a Single-Step Three-Component Reaction Organometallics 2013, 32, 6098-6105
    • (2013) Organometallics , vol.32 , pp. 6098-6105
    • Patra, M.1    Hess, J.2    Konatschnig, S.3    Spingler, B.4    Gasser, G.5
  • 30
    • 84873622270 scopus 로고    scopus 로고
    • Metal-Arene Complexes with Indolo[3,2- c ]quinolines: Effects of Ruthenium vs Osmium and Modifications of the Lactam Unit on Intermolecular Interactions, Anticancer Activity, Cell Cycle, and Cellular Accumulation
    • Filak, L. K.; Goschl, S.; Heffeter, P.; Ghannadzadeh Samper, K.; Egger, A. E.; Jakupec, M. A.; Keppler, B. K.; Berger, W.; Arion, V. B. Metal-Arene Complexes with Indolo[3,2- c ]quinolines: Effects of Ruthenium vs Osmium and Modifications of the Lactam Unit on Intermolecular Interactions, Anticancer Activity, Cell Cycle, and Cellular Accumulation Organometallics 2013, 32, 903-914
    • (2013) Organometallics , vol.32 , pp. 903-914
    • Filak, L.K.1    Goschl, S.2    Heffeter, P.3    Ghannadzadeh Samper, K.4    Egger, A.E.5    Jakupec, M.A.6    Keppler, B.K.7    Berger, W.8    Arion, V.B.9
  • 31
    • 0000717888 scopus 로고
    • Benzene Complexes of Ruthenium(II)
    • Zelonka, R. A.; Baird, M. C. Benzene Complexes of Ruthenium(II) Can. J. Chem. 1972, 50, 3063-3072
    • (1972) Can. J. Chem. , vol.50 , pp. 3063-3072
    • Zelonka, R.A.1    Baird, M.C.2
  • 34
    • 0023130372 scopus 로고
    • Evaluation of a Tetrazolium-Based Semiautomated Colorimetric Assay: Assessment of Chemosensitivity Testing
    • Carmichael, J.; DeGraff, W. G.; Gazdar, A. F.; Minna, J. D.; Mitchell, J. B. Evaluation of a Tetrazolium-Based Semiautomated Colorimetric Assay: Assessment of Chemosensitivity Testing Cancer Res. 1987, 47, 936-942
    • (1987) Cancer Res. , vol.47 , pp. 936-942
    • Carmichael, J.1    Degraff, W.G.2    Gazdar, A.F.3    Minna, J.D.4    Mitchell, J.B.5
  • 36
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings
    • Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and Computational Approaches To Estimate Solubility and Permeability in Drug Discovery and Development Settings Adv. Drug Delivery Rev. 1997, 23, 3-25
    • (1997) Adv. Drug Delivery Rev. , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 37
    • 0037030653 scopus 로고    scopus 로고
    • Molecular Properties That Influence the Oral Bioavailability of Drug Candidates
    • Veber, D. F.; Johnson, S. R.; Cheng, H.; Smith, B. R.; Ward, K. W.; Kopple, K. D. Molecular Properties That Influence the Oral Bioavailability of Drug Candidates J. Med. Chem. 2002, 45, 2625-2623
    • (2002) J. Med. Chem. , vol.45 , pp. 2625-2623
    • Veber, D.F.1    Johnson, S.R.2    Cheng, H.3    Smith, B.R.4    Ward, K.W.5    Kopple, K.D.6
  • 39
    • 84883216617 scopus 로고    scopus 로고
    • Ruthenium-Arene-β-Carboline Complexes as Potent Inhibitors of Cyclin-Dependent Kinase 1: Synthesis, Characterization and Anticancer Mechanism Studies
    • He, L.; Liao, S. Y.; Tan, C. P.; Ye, R. R.; Xu, Y. W.; Zhao, M.; Ji, L. N.; Mao, Z. W. Ruthenium-Arene-β-Carboline Complexes as Potent Inhibitors of Cyclin-Dependent Kinase 1: Synthesis, Characterization and Anticancer Mechanism Studies Chem.-Eur. J. 2013, 19, 12152-12160
    • (2013) Chem.-Eur. J. , vol.19 , pp. 12152-12160
    • He, L.1    Liao, S.Y.2    Tan, C.P.3    Ye, R.R.4    Xu, Y.W.5    Zhao, M.6    Ji, L.N.7    Mao, Z.W.8
  • 41
    • 0037141471 scopus 로고    scopus 로고
    • In Vitro and in Vivo Activity and Cross Resistance Profiles of Novel Ruthenium (II) Organometallic Arene Complexes in Human Ovarian Cancer
    • Aird, R. E.; Cummings, J.; Ritchie, A. A.; Muir, M.; Morris, R. E.; Chen, H.; Sadler, P. J.; Jodrell, D. I. In Vitro and in Vivo Activity and Cross Resistance Profiles of Novel Ruthenium (II) Organometallic Arene Complexes in Human Ovarian Cancer Br. J. Cancer 2002, 86, 1652-1657
    • (2002) Br. J. Cancer , vol.86 , pp. 1652-1657
    • Aird, R.E.1    Cummings, J.2    Ritchie, A.A.3    Muir, M.4    Morris, R.E.5    Chen, H.6    Sadler, P.J.7    Jodrell, D.I.8
  • 42
    • 77956187622 scopus 로고    scopus 로고
    • Roscovitine-based CDK Inhibitors Acting as N-Donor Ligands in the Platinum(II) Oxalato Complexes: Preparation, Characterization and in Vitro Cytotoxicity
    • Travnicek, Z.; Starha, P.; Popa, I.; Vrzal, R.; Dvorak, Z. Roscovitine-based CDK Inhibitors Acting as N-Donor Ligands in the Platinum(II) Oxalato Complexes: Preparation, Characterization and in Vitro Cytotoxicity Eur. J. Med. Chem. 2010, 45, 4609-4614
    • (2010) Eur. J. Med. Chem. , vol.45 , pp. 4609-4614
    • Travnicek, Z.1    Starha, P.2    Popa, I.3    Vrzal, R.4    Dvorak, Z.5
  • 46
    • 1642327569 scopus 로고    scopus 로고
    • Characterization of p53 Wild-Type and Null Isogenic Colorectal Cancer Cell Lines Resistant to 5-Fluorouracil, Oxaliplatin, and Irinotecan
    • Boyer, J.; McLean, E. G.; Aroori, S.; Wilson, P.; McCulla, A.; Carey, P. D.; Longley, D. B.; Johnston, P. G. Characterization of p53 Wild-Type and Null Isogenic Colorectal Cancer Cell Lines Resistant to 5-Fluorouracil, Oxaliplatin, and Irinotecan Clin. Cancer Res. 2004, 10, 2158-2167
    • (2004) Clin. Cancer Res. , vol.10 , pp. 2158-2167
    • Boyer, J.1    McLean, E.G.2    Aroori, S.3    Wilson, P.4    McCulla, A.5    Carey, P.D.6    Longley, D.B.7    Johnston, P.G.8
  • 47
    • 0042697468 scopus 로고    scopus 로고
    • The JNK, ERK and p53 Pathways Play Distinct Roles in Apoptosis Mediated by the Antitumor Agents Vinblastine, Doxorubicin, and Etoposide
    • Brantley-Finley, C.; Lyle, C. S.; Du, L.; Goodwin, M. E.; Hall, T.; Szwedo, D.; Kaushal, G. P.; Chambers, T. C. The JNK, ERK and p53 Pathways Play Distinct Roles in Apoptosis Mediated by the Antitumor Agents Vinblastine, Doxorubicin, and Etoposide Biochem. Pharmacol. 2003, 66, 459-469
    • (2003) Biochem. Pharmacol. , vol.66 , pp. 459-469
    • Brantley-Finley, C.1    Lyle, C.S.2    Du, L.3    Goodwin, M.E.4    Hall, T.5    Szwedo, D.6    Kaushal, G.P.7    Chambers, T.C.8
  • 48
    • 51849085127 scopus 로고    scopus 로고
    • The Ruthenium(II)-Arene Compound RAPTA-C Induces Apoptosis in EAC Cells Through Mitochondrial and p53-JNK Pathways
    • Chatterjee, S.; Kundu, S.; Bhattacharyya, A.; Hartinger, C. G.; Dyson, P. J. The Ruthenium(II)-Arene Compound RAPTA-C Induces Apoptosis in EAC Cells Through Mitochondrial and p53-JNK Pathways J. Biol. Inorg. Chem. 2008, 13, 1149-1155
    • (2008) J. Biol. Inorg. Chem. , vol.13 , pp. 1149-1155
    • Chatterjee, S.1    Kundu, S.2    Bhattacharyya, A.3    Hartinger, C.G.4    Dyson, P.J.5
  • 49
    • 18744371055 scopus 로고    scopus 로고
    • Investigation of the Role of Bax, p21/Waf1 and p53 as Determinants of Cellular Responses in HCT116 Colorectal Cancer Cells Exposed to the Novel Cytotoxic Ruthenium(II) Organometallic Agent, RM175
    • Hayward, R. L.; Schornagel, Q. C.; Tente, R.; Macpherson, J. S.; Aird, R. E.; Guichard, S.; Habtemariam, A.; Sadler, P.; Jodrell, D. I. Investigation of the Role of Bax, p21/Waf1 and p53 as Determinants of Cellular Responses in HCT116 Colorectal Cancer Cells Exposed to the Novel Cytotoxic Ruthenium(II) Organometallic Agent, RM175 Cancer Chemother. Pharmacol. 2005, 55, 577-583
    • (2005) Cancer Chemother. Pharmacol. , vol.55 , pp. 577-583
    • Hayward, R.L.1    Schornagel, Q.C.2    Tente, R.3    Macpherson, J.S.4    Aird, R.E.5    Guichard, S.6    Habtemariam, A.7    Sadler, P.8    Jodrell, D.I.9
  • 51
    • 84866340471 scopus 로고    scopus 로고
    • Tuning the Activity of Platinum(IV) Anticancer Complexes Through Asymmetric Acylation
    • Chin, C. F.; Tian, Q.; Setyawati, M. I.; Fang, W.; Tan, E. S.; Leong, D. T.; Ang, W. H. Tuning the Activity of Platinum(IV) Anticancer Complexes Through Asymmetric Acylation J. Med. Chem. 2012, 55, 7571-7582
    • (2012) J. Med. Chem. , vol.55 , pp. 7571-7582
    • Chin, C.F.1    Tian, Q.2    Setyawati, M.I.3    Fang, W.4    Tan, E.S.5    Leong, D.T.6    Ang, W.H.7
  • 53
    • 0035822755 scopus 로고    scopus 로고
    • 2(pta)] (pta = 1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane): A Water Soluble Compound that Exhibits pH Dependent DNA Binding Providing Selectivity for Diseased Cells
    • 2(pta)] (pta = 1,3,5-triaza-7-phosphatricyclo[3.3.1.1]decane): A Water Soluble Compound that Exhibits pH Dependent DNA Binding Providing Selectivity for Diseased Cells Chem. Commun. 2001, 15, 1396-1397
    • (2001) Chem. Commun. , vol.15 , pp. 1396-1397
    • Allardyce, C.S.1    Dyson, P.J.2    Ellis, D.J.3    Heath, S.L.4
  • 55
    • 0000126960 scopus 로고
    • 4-Bonding in (Arene)ruthenium Complexes of Octamethylnapthalene
    • 4-Bonding in (Arene)ruthenium Complexes of Octamethylnapthalene Organometallics 1982, 3, 605-613
    • (1982) Organometallics , vol.3 , pp. 605-613
    • Hull, J.W.J.1    Gladfelter, W.L.2
  • 57
    • 37049118608 scopus 로고
    • Arene Ruthenium(II) Complexes Formed by Dehydrogenation of Cyclo-hexadienes with Ruthenium(III) Trichloride
    • Bennett, M. A.; Smith, A. K. Arene Ruthenium(II) Complexes Formed by Dehydrogenation of Cyclo-hexadienes with Ruthenium(III) Trichloride J. Chem. Soc., Dalton Trans. 1974, 223-241
    • (1974) J. Chem. Soc., Dalton Trans. , pp. 223-241
    • Bennett, M.A.1    Smith, A.K.2
  • 58
    • 84905029246 scopus 로고    scopus 로고
    • SMART, version 5.628; Bruker AXS Inc. Madison, WI.
    • SMART, version 5.628; Bruker AXS Inc.: Madison, WI, 2001.
    • (2001)
  • 59
    • 84905029247 scopus 로고    scopus 로고
    • SAINT +, version 6.22a; Bruker AXS Inc. Madison, WI.
    • SAINT +, version 6.22a; Bruker AXS Inc.: Madison, WI, 2001.
    • (2001)
  • 60
    • 84905055774 scopus 로고    scopus 로고
    • SADABS, University of Gottingen: Gottingen, Germany.
    • Sheldrick, G. W. SADABS, University of Gottingen: Gottingen, Germany, 2001.
    • (2001)
    • Sheldrick, G.W.1
  • 61
    • 84904977844 scopus 로고    scopus 로고
    • SHELXTL, version 6.14; Bruker AXS Inc. Madison, WI.
    • SHELXTL, version 6.14; Bruker AXS Inc.: Madison, WI, 2000.
    • (2000)
  • 62
    • 0036046535 scopus 로고    scopus 로고
    • Plasma Membrane Phospholipid Asymmetry
    • Quinn, P. J. Plasma Membrane Phospholipid Asymmetry Subcell. Biochem. 2002, 36, 1-25
    • (2002) Subcell. Biochem. , vol.36 , pp. 1-25
    • Quinn, P.J.1


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