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Volumn 56, Issue 1, 2013, Pages 182-200

Synthesis and biological evaluation of indenoisoquinolines that inhibit both tyrosyl-DNA phosphodiesterase i (Tdp1) and topoisomerase i (Top1)

Author keywords

[No Author keywords available]

Indexed keywords

DNA TOPOISOMERASE; INDENOISOQUINOLINE; ISOQUINOLINE DERIVATIVE; PHOSPHODIESTERASE I; TYROSYL DNA PHOSPHODIESTERASE I; UNCLASSIFIED DRUG;

EID: 84872336712     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3014458     Document Type: Article
Times cited : (65)

References (37)
  • 1
    • 0035834150 scopus 로고    scopus 로고
    • The Tyrosyl-DNA Phosphodiesterase Tdp1 Is a Member of the Phospholipase D Superfamily
    • Interthal, H.; Pouliott, J. J.; Champoux, J. J. The Tyrosyl-DNA Phosphodiesterase Tdp1 Is a Member of the Phospholipase D Superfamily Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 12009-12014
    • (2001) Proc. Natl. Acad. Sci. U.S.A. , vol.98 , pp. 12009-12014
    • Interthal, H.1    Pouliott, J.J.2    Champoux, J.J.3
  • 3
    • 0036178630 scopus 로고    scopus 로고
    • The Crystal Structure of Human Tyrosyl-DNA Phosphodiesterase, Tdp1
    • Davies, D. R.; Interthal, H.; Champoux, J. J.; Hol, W. G. J. The Crystal Structure of Human Tyrosyl-DNA Phosphodiesterase, Tdp1 Structure 2002, 10, 237-248
    • (2002) Structure , vol.10 , pp. 237-248
    • Davies, D.R.1    Interthal, H.2    Champoux, J.J.3    Hol, W.G.J.4
  • 4
    • 77954187741 scopus 로고    scopus 로고
    • DNA Topoisomerases and Their Poisoning by Anticancer and Antibacterial Drugs
    • Pommier, Y.; Leo, E.; Zhang, H. L.; Marchand, C. DNA Topoisomerases and Their Poisoning by Anticancer and Antibacterial Drugs Chem. Biol. 2010, 17, 421-433
    • (2010) Chem. Biol. , vol.17 , pp. 421-433
    • Pommier, Y.1    Leo, E.2    Zhang, H.L.3    Marchand, C.4
  • 6
    • 0037073479 scopus 로고    scopus 로고
    • Insights into Substrate Binding and Catalytic Mechanism of Human Tyrosyl-DNA Phosphodiesterase (Tdp1) from Vanadate and Tungstate-inhibited Structures
    • Davies, D. R.; Interthal, H.; Champoux, J. J.; Hol, W. G. J. Insights into Substrate Binding and Catalytic Mechanism of Human Tyrosyl-DNA Phosphodiesterase (Tdp1) from Vanadate and Tungstate-inhibited Structures J. Mol. Biol. 2002, 324, 917-932
    • (2002) J. Mol. Biol. , vol.324 , pp. 917-932
    • Davies, D.R.1    Interthal, H.2    Champoux, J.J.3    Hol, W.G.J.4
  • 7
    • 0034124053 scopus 로고    scopus 로고
    • Conversion of Topoisomerase 1 Cleavage Complexes on the Leading Strand of Ribosomal DNA into 5 ′-Phosphorylated DNA Double-strand Breaks by Replication Runoff
    • Strumberg, D.; Pilon, A. A.; Smith, M.; Hickey, R.; Malkas, L.; Pommier, Y. Conversion of Topoisomerase 1 Cleavage Complexes on the Leading Strand of Ribosomal DNA into 5 ′-Phosphorylated DNA Double-strand Breaks by Replication Runoff Mol. Cell. Biol. 2000, 20, 3977-3987
    • (2000) Mol. Cell. Biol. , vol.20 , pp. 3977-3987
    • Strumberg, D.1    Pilon, A.A.2    Smith, M.3    Hickey, R.4    Malkas, L.5    Pommier, Y.6
  • 8
    • 66849113688 scopus 로고    scopus 로고
    • The Indenoisoquinoline Noncamptothecin Topoisomerase i Inhibitors: Update and Perspectives
    • Pommier, Y.; Cushman, M. The Indenoisoquinoline Noncamptothecin Topoisomerase I Inhibitors: Update and Perspectives Mol. Cancer Ther. 2009, 8, 1008-1014
    • (2009) Mol. Cancer Ther. , vol.8 , pp. 1008-1014
    • Pommier, Y.1    Cushman, M.2
  • 9
    • 84855347756 scopus 로고    scopus 로고
    • Interfacial Inhibitors: Targeting Macromolecular Complexes
    • Pommier, Y.; Marchand, C. Interfacial Inhibitors: Targeting Macromolecular Complexes Nat. Rev. Drug Discovery 2012, 11, 25-36
    • (2012) Nat. Rev. Drug Discovery , vol.11 , pp. 25-36
    • Pommier, Y.1    Marchand, C.2
  • 10
    • 77953489820 scopus 로고    scopus 로고
    • Tyrosyl-DNA Phosphodiesterase 1 Targeting for Modulation of Camptothecin-Based Treatment
    • Beretta, G. L.; Cossa, G.; Gatti, L.; Zunino, F.; Perego, P. Tyrosyl-DNA Phosphodiesterase 1 Targeting for Modulation of Camptothecin-Based Treatment Curr. Med. Chem. 2010, 17, 1500-1508
    • (2010) Curr. Med. Chem. , vol.17 , pp. 1500-1508
    • Beretta, G.L.1    Cossa, G.2    Gatti, L.3    Zunino, F.4    Perego, P.5
  • 11
    • 0034871092 scopus 로고    scopus 로고
    • Pathways for Repair of Topoisomerase i Covalent Complexes in Saccharomyces cerevisiae
    • Pouliot, J. J.; Robertson, C. A.; Nash, H. A. Pathways for Repair of Topoisomerase I Covalent Complexes in Saccharomyces cerevisiae Genes Cells 2001, 6, 677-687
    • (2001) Genes Cells , vol.6 , pp. 677-687
    • Pouliot, J.J.1    Robertson, C.A.2    Nash, H.A.3
  • 12
    • 34547829271 scopus 로고    scopus 로고
    • Novel High-Throughput Electrochemiluminescent Assay for Identification of Human Tyrosyl-DNA Phosphodiesterase (Tdp1) Inhibitors and Characterization of Furamidine (NSC 305831) as an Inhibitor of Tdp1
    • Antony, S.; Marchand, C.; Stephen, A. G.; Thibaut, L.; Agama, K. K.; Fisher, R. J.; Pommier, Y. Novel High-Throughput Electrochemiluminescent Assay for Identification of Human Tyrosyl-DNA Phosphodiesterase (Tdp1) Inhibitors and Characterization of Furamidine (NSC 305831) as an Inhibitor of Tdp1 Nucleic Acids Res. 2007, 35, 4474-4484
    • (2007) Nucleic Acids Res. , vol.35 , pp. 4474-4484
    • Antony, S.1    Marchand, C.2    Stephen, A.G.3    Thibaut, L.4    Agama, K.K.5    Fisher, R.J.6    Pommier, Y.7
  • 13
    • 77949261473 scopus 로고    scopus 로고
    • Corrigendum to "inhibitors of Human Tyrosyl-DNA Phospodiesterase (hTdp1) Developed by Virtual Screening Using Ligand-based Pharmacophores"
    • Weidlich, I. E.; Dexheimer, T.; Marchand, C.; Antony, S.; Pommier, Y.; Nicklaus, M. C. Corrigendum to "Inhibitors of Human Tyrosyl-DNA Phospodiesterase (hTdp1) Developed by Virtual Screening Using Ligand-based Pharmacophores" Bioorg. Med. Chem. 2010, 18, 2346-2346
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 2346-2346
    • Weidlich, I.E.1    Dexheimer, T.2    Marchand, C.3    Antony, S.4    Pommier, Y.5    Nicklaus, M.C.6
  • 14
    • 77949273813 scopus 로고    scopus 로고
    • Virtual Screening Using Ligand-based Pharmacophores for Inhibitors of Human Tyrosyl-DNA Phospodiesterase (hTdp1)
    • Weidlich, I. E.; Dexheimer, T.; Marahiel, M. A.; Antony, S.; Pommier, Y.; Nicklaus, M. C. Virtual Screening Using Ligand-based Pharmacophores for Inhibitors of Human Tyrosyl-DNA Phospodiesterase (hTdp1) Bioorg. Med. Chem. 2010, 18, 2347-2355
    • (2010) Bioorg. Med. Chem. , vol.18 , pp. 2347-2355
    • Weidlich, I.E.1    Dexheimer, T.2    Marahiel, M.A.3    Antony, S.4    Pommier, Y.5    Nicklaus, M.C.6
  • 18
    • 84859078546 scopus 로고    scopus 로고
    • Induction of Apoptosis by 3-Amino-6-(3-aminopropyl)-5,6-dihydro-5,11- dioxo-11 H -indeno[1,2- c ]isoquinoline via Modulation of MAPKs (p38 and c-Jun N-terminal Kinase) and c-Myc in HL-60 Human Leukemia Cells
    • Park, E.-J.; Kiselev, E.; Conda-Sheridan, M.; Cushman, M.; Pezzuto, J. M. Induction of Apoptosis by 3-Amino-6-(3-aminopropyl)-5,6-dihydro-5,11-dioxo-11 H -indeno[1,2- c ]isoquinoline via Modulation of MAPKs (p38 and c-Jun N-terminal Kinase) and c-Myc in HL-60 Human Leukemia Cells J. Nat. Prod. 2011, 75, 378-384
    • (2011) J. Nat. Prod. , vol.75 , pp. 378-384
    • Park, E.-J.1    Kiselev, E.2    Conda-Sheridan, M.3    Cushman, M.4    Pezzuto, J.M.5
  • 20
    • 33845955224 scopus 로고    scopus 로고
    • A Systematic Study of Nitrated Indenoisoquinolines Reveals a Potent Topoisomerase i Inhibitor
    • Morrell, A.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Cushman, M. A Systematic Study of Nitrated Indenoisoquinolines Reveals a Potent Topoisomerase I Inhibitor J. Med. Chem. 2006, 49, 7740-7753
    • (2006) J. Med. Chem. , vol.49 , pp. 7740-7753
    • Morrell, A.1    Antony, S.2    Kohlhagen, G.3    Pommier, Y.4    Cushman, M.5
  • 21
  • 22
    • 0007565558 scopus 로고
    • Stereoselective Oxidation by Thionyl Chloride Leading to the Indeno[1,2- c ]isoquinoline System
    • Cushman, M.; Cheng, L. Stereoselective Oxidation by Thionyl Chloride Leading to the Indeno[1,2- c ]isoquinoline System J. Org. Chem. 1978, 43, 3781-3783
    • (1978) J. Org. Chem. , vol.43 , pp. 3781-3783
    • Cushman, M.1    Cheng, L.2
  • 25
    • 41149095109 scopus 로고    scopus 로고
    • Reactivity of N-(Omega-haloalkyl)-Beta-Lactams with Regard to Lithium Aluminium Hydride: Novel Synthesis of 1-(1-Aryl-3-hydroxypropyl)aziridines and 3-Aryl-3-(N-propylamino)propan-1-ols
    • D'Hooghe, M.; Dekeukeleire, S.; De Kimpe, N. Reactivity of N-(Omega-haloalkyl)-Beta-Lactams with Regard to Lithium Aluminium Hydride: Novel Synthesis of 1-(1-Aryl-3-hydroxypropyl)aziridines and 3-Aryl-3-(N-propylamino) propan-1-ols Org. Biomol. Chem. 2008, 6, 1190-1196
    • (2008) Org. Biomol. Chem. , vol.6 , pp. 1190-1196
    • D'Hooghe, M.1    Dekeukeleire, S.2    De Kimpe, N.3
  • 26
    • 7444233119 scopus 로고    scopus 로고
    • Synthesis and Anticancer Activity of Simplified Indenoisoquinoline Topoisomerase i Inhibitors Lacking Substituents on the Aromatic Rings
    • Nagarajan, M.; Morrell, A.; Fort, B. C.; Meckley, M. R.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Cushman, M. Synthesis and Anticancer Activity of Simplified Indenoisoquinoline Topoisomerase I Inhibitors Lacking Substituents on the Aromatic Rings J. Med. Chem. 2004, 47, 5651-5661
    • (2004) J. Med. Chem. , vol.47 , pp. 5651-5661
    • Nagarajan, M.1    Morrell, A.2    Fort, B.C.3    Meckley, M.R.4    Antony, S.5    Kohlhagen, G.6    Pommier, Y.7    Cushman, M.8
  • 27
    • 33144472888 scopus 로고    scopus 로고
    • Synthesis of Benz[ d ]indeno[1,2- b ]pyran-5,11-diones: Versatile Intermediates for the Design and Synthesis of Topoisomerase i Inhibitors
    • Morrell, A.; Antony, S.; Kohlhagen, G.; Pommier, Y.; Cushman, M. Synthesis of Benz[ d ]indeno[1,2- b ]pyran-5,11-diones: Versatile Intermediates for the Design and Synthesis of Topoisomerase I Inhibitors Bioorg. Med. Chem. Lett. 2006, 16, 1846-1849
    • (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 1846-1849
    • Morrell, A.1    Antony, S.2    Kohlhagen, G.3    Pommier, Y.4    Cushman, M.5
  • 28
    • 79955568490 scopus 로고    scopus 로고
    • Benzannulation for the Regiodefined Synthesis of 2-Alkyl/Aryl-1- naphthols: Total Synthesis of Arnottin i
    • Mal, D.; Jana, A. K.; Mitra, P.; Ghosh, K. Benzannulation for the Regiodefined Synthesis of 2-Alkyl/Aryl-1-naphthols: Total Synthesis of Arnottin I J. Org. Chem. 2011, 76, 3392-3398
    • (2011) J. Org. Chem. , vol.76 , pp. 3392-3398
    • Mal, D.1    Jana, A.K.2    Mitra, P.3    Ghosh, K.4
  • 30
    • 84871435760 scopus 로고    scopus 로고
    • Tripos Int. St. Louis
    • SYBYL 8.0, Tripos Int.: St. Louis.
    • SYBYL 8.0
  • 31
    • 58749110485 scopus 로고    scopus 로고
    • DNA Cleavage Assay for the Identification of Topoisomerase i Inhibitors
    • Dexheimer, T. S.; Pommier, Y. DNA Cleavage Assay for the Identification of Topoisomerase I Inhibitors Nat. Protoc. 2008, 3, 1736-1750
    • (2008) Nat. Protoc. , vol.3 , pp. 1736-1750
    • Dexheimer, T.S.1    Pommier, Y.2
  • 33
    • 0242610818 scopus 로고    scopus 로고
    • Differential Induction of Topoisomerase I-DNA Cleavage Complexes by the Indenoisoquinoline MJ-III-65 (NSC 706744) and Camptothecin: Base Sequence Analysis and Activity against Camptothecin-Resistant Topoisomerase i
    • Antony, S.; Jayaraman, M.; Laco, G.; Kohlhagen, G.; Kohn, K. W.; Cushman, M.; Pommier, Y. Differential Induction of Topoisomerase I-DNA Cleavage Complexes by the Indenoisoquinoline MJ-III-65 (NSC 706744) and Camptothecin: Base Sequence Analysis and Activity against Camptothecin-Resistant Topoisomerase I Cancer Res. 2003, 63, 7428-7435
    • (2003) Cancer Res. , vol.63 , pp. 7428-7435
    • Antony, S.1    Jayaraman, M.2    Laco, G.3    Kohlhagen, G.4    Kohn, K.W.5    Cushman, M.6    Pommier, Y.7
  • 34
    • 13444284042 scopus 로고    scopus 로고
    • Cellular Topoisomerase i Inhibition and Antiproliferative Activity by MJ-III-65 (NSC 706744), an Indenoisoquinoline Topoisomerase i Poison
    • Antony, S.; Kohlhagen, G.; Agama, K.; Jayaraman, M.; Cao, S.; Durrani, F. A.; Rustum, Y. M.; Cushman, M.; Pommier, Y. Cellular Topoisomerase I Inhibition and Antiproliferative Activity by MJ-III-65 (NSC 706744), an Indenoisoquinoline Topoisomerase I Poison Mol. Pharmacol. 2005, 67, 523-530
    • (2005) Mol. Pharmacol. , vol.67 , pp. 523-530
    • Antony, S.1    Kohlhagen, G.2    Agama, K.3    Jayaraman, M.4    Cao, S.5    Durrani, F.A.6    Rustum, Y.M.7    Cushman, M.8    Pommier, Y.9
  • 37
    • 84863910171 scopus 로고    scopus 로고
    • CellMiner: A Web-Based Suite of Genomic and Pharrmacologic Tools to Explore Transcript and Drug Patterns in the NCI-60 Cell Line Set
    • Reinhold, W. C.; Sunshine, M.; Liu, H.; Varma, S.; Kohn, K. W.; Morris, J.; Doroshow, J.; Pommier, Y. CellMiner: A Web-Based Suite of Genomic and Pharrmacologic Tools to Explore Transcript and Drug Patterns in the NCI-60 Cell Line Set Cancer Res. 2012, 72, 3499-3511
    • (2012) Cancer Res. , vol.72 , pp. 3499-3511
    • Reinhold, W.C.1    Sunshine, M.2    Liu, H.3    Varma, S.4    Kohn, K.W.5    Morris, J.6    Doroshow, J.7    Pommier, Y.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.