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Volumn 51, Issue 18, 2008, Pages 5566-5574

Aminoacyl-anthraquinone conjugates as telomerase inhibitors: Synthesis, biophysical and biological evaluation

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRAQUINONE DERIVATIVE; TELOMERASE; TELOMERASE INHIBITOR;

EID: 52449117457     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm800160v     Document Type: Article
Times cited : (60)

References (35)
  • 1
    • 34249907843 scopus 로고    scopus 로고
    • Wells, R. D. Non-B DNA conformations, mutagenesis and disease. Trends Biochem. Sci. 2007, 32, 271-278.
    • Wells, R. D. Non-B DNA conformations, mutagenesis and disease. Trends Biochem. Sci. 2007, 32, 271-278.
  • 2
    • 1042268168 scopus 로고    scopus 로고
    • 40 years later: From 5′-GMP to molecular biology and supramolecular chemistry
    • Davis, J. T. G-quartets 40 years later: from 5′-GMP to molecular biology and supramolecular chemistry. Angew. Chem., Int. Ed. 2000, 43, 668-698.
    • (2000) Angew. Chem., Int. Ed , vol.43 , pp. 668-698
    • Davis, J.1    G-quartets, T.2
  • 4
    • 33646831821 scopus 로고    scopus 로고
    • Telomeres, chromosome instability and cancer
    • Bailey, S. M.; Murnane, J. P. Telomeres, chromosome instability and cancer. Nucleic Acids Res. 2006, 34, 2408-2417.
    • (2006) Nucleic Acids Res , vol.34 , pp. 2408-2417
    • Bailey, S.M.1    Murnane, J.P.2
  • 5
    • 35848943879 scopus 로고    scopus 로고
    • Telomere Length Profiles in Humans: All Ends are Not Equal
    • Gilson, E.; Londono-Vallejo, A. Telomere Length Profiles in Humans: All Ends are Not Equal. Cell Cycle 2007, 6, 2486-2494.
    • (2007) Cell Cycle , vol.6 , pp. 2486-2494
    • Gilson, E.1    Londono-Vallejo, A.2
  • 6
    • 0035929353 scopus 로고    scopus 로고
    • Switching and signaling at the telomere
    • Blackburn, E. H. Switching and signaling at the telomere. Cell 2001, 106, 61-73.
    • (2001) Cell , vol.106 , pp. 61-73
    • Blackburn, E.H.1
  • 7
    • 0031010342 scopus 로고    scopus 로고
    • A survey of telomerase activity in human cancer
    • Shay, J. W.; Bacchetti, S. A survey of telomerase activity in human cancer. Eur. J. Cancer 1997, 33, 787-791.
    • (1997) Eur. J. Cancer , vol.33 , pp. 787-791
    • Shay, J.W.1    Bacchetti, S.2
  • 8
    • 34548857357 scopus 로고    scopus 로고
    • Targeting the limitless replicative potential of cancer: The telomerase/telomere pathway
    • Kelland, L. Targeting the limitless replicative potential of cancer: the telomerase/telomere pathway. Clin. Cancer Res. 2007, 13, 4960-4963.
    • (2007) Clin. Cancer Res , vol.13 , pp. 4960-4963
    • Kelland, L.1
  • 9
    • 33847372902 scopus 로고    scopus 로고
    • Physiological relevance of telomeric G-quadruplex formation: A potential drug target
    • (a) Oganesian, L.; Bryan, T. M. Physiological relevance of telomeric G-quadruplex formation: a potential drug target. Bioessays 2007, 29, 155-165.
    • (2007) Bioessays , vol.29 , pp. 155-165
    • Oganesian, L.1    Bryan, T.M.2
  • 10
    • 34548400444 scopus 로고    scopus 로고
    • Energetics of quadruplex-drug recognition in anticancer therapy
    • (b) Pagano, B.; Giancola, C. Energetics of quadruplex-drug recognition in anticancer therapy. Curr. Cancer Drug Targets 2007, 7, 520-540.
    • (2007) Curr. Cancer Drug Targets , vol.7 , pp. 520-540
    • Pagano, B.1    Giancola, C.2
  • 12
    • 4444304085 scopus 로고    scopus 로고
    • G-quadruplex interacting agents targeting the telomeric G-overhang are more than simple telomerase inhibitors
    • (d) Riou, J. F. G-quadruplex interacting agents targeting the telomeric G-overhang are more than simple telomerase inhibitors. Curr. Med. Chem. Anticancer Agents 2004, 4, 439-443.
    • (2004) Curr. Med. Chem. Anticancer Agents , vol.4 , pp. 439-443
    • Riou, J.F.1
  • 14
    • 0037070575 scopus 로고    scopus 로고
    • Kim, M. Y.; Vankayalapati, H.; Shin-Ya, K.; Wierzba, K.; Hurley, L. H. Telomestatin, a potent telomerase inhibitor that interacts quite specifically with the human telomeric intramolecular G-quadruplex. J. Am. Chem. Soc. 2002, 124, 2098-2099.
    • (b) Kim, M. Y.; Vankayalapati, H.; Shin-Ya, K.; Wierzba, K.; Hurley, L. H. Telomestatin, a potent telomerase inhibitor that interacts quite specifically with the human telomeric intramolecular G-quadruplex. J. Am. Chem. Soc. 2002, 124, 2098-2099.
  • 15
    • 6944239985 scopus 로고    scopus 로고
    • Leonetti, C.; Amodei, S.; D'Angelo, C.; Rizzo, A.; Benassi, B.; Antonelli, A.; Elli, R.; Stevens, M. F. G.; D'Incalci, M.; Zupi, G.; Biroccio, A. Biological activity of the G-quadruplex ligand RHPS4(3,11-difluoro-6,8,13- trimethyl-8H-quino[4,3,2-kl]acridinium methosulfate) is associated with telomere capping alteration. Mol. Pharm. 2004, 66, 1138-1146.
    • (c) Leonetti, C.; Amodei, S.; D'Angelo, C.; Rizzo, A.; Benassi, B.; Antonelli, A.; Elli, R.; Stevens, M. F. G.; D'Incalci, M.; Zupi, G.; Biroccio, A. Biological activity of the G-quadruplex ligand RHPS4(3,11-difluoro-6,8,13- trimethyl-8H-quino[4,3,2-kl]acridinium methosulfate) is associated with telomere capping alteration. Mol. Pharm. 2004, 66, 1138-1146.
  • 16
    • 20944447769 scopus 로고    scopus 로고
    • Apoptosis related to telomere instability and cell cycle alterations in human glioma cells treated by new highly selective G-quadruplex ligands
    • (d) Pennarun, G.; Granotier, C.; Gauthier, L. R.; Gomez, D.; Hoffschir, F.; Mandine, E.; Riou, J.-F.; Mergny, J.-L.; Maillet, P.; Boussin, F. D. Apoptosis related to telomere instability and cell cycle alterations in human glioma cells treated by new highly selective G-quadruplex ligands. Oncogene 2005, 24, 2917-2928.
    • (2005) Oncogene , vol.24 , pp. 2917-2928
    • Pennarun, G.1    Granotier, C.2    Gauthier, L.R.3    Gomez, D.4    Hoffschir, F.5    Mandine, E.6    Riou, J.-F.7    Mergny, J.-L.8    Maillet, P.9    Boussin, F.D.10
  • 17
    • 39049147645 scopus 로고    scopus 로고
    • A hitchhiker's guide to G-quadruplex ligands
    • (e) Monchaud, D.; Teulade-Fichou, M.-P. A hitchhiker's guide to G-quadruplex ligands. Org. Biomol. Chem. 2008, 6, 627-636.
    • (2008) Org. Biomol. Chem , vol.6 , pp. 627-636
    • Monchaud, D.1    Teulade-Fichou, M.-P.2
  • 18
    • 0022340391 scopus 로고
    • Characteristics of the binding of the anticancer agents mitoxantrone and ametantrone and related structures to deoxyribonucleic acids
    • Lown, J. W.; Morgan, A. R.; Yen, S. F.; Wang, Y. H.; Wilson, W. D. Characteristics of the binding of the anticancer agents mitoxantrone and ametantrone and related structures to deoxyribonucleic acids. Biochemistry 1985, 24, 4028-4035.
    • (1985) Biochemistry , vol.24 , pp. 4028-4035
    • Lown, J.W.1    Morgan, A.R.2    Yen, S.F.3    Wang, Y.H.4    Wilson, W.D.5
  • 19
    • 0023922254 scopus 로고
    • Synthesis, molecular modeling, DNA binding, and antitumor properties of some substituted amidoanthraquinones
    • (a) Collier, D. A.; Neidle, S. Synthesis, molecular modeling, DNA binding, and antitumor properties of some substituted amidoanthraquinones. J. Med. Chem. 1988, 31, 847-857.
    • (1988) J. Med. Chem , vol.31 , pp. 847-857
    • Collier, D.A.1    Neidle, S.2
  • 21
    • 0032514479 scopus 로고    scopus 로고
    • 1,4- and 2,6-disubstituted amidoanthracene-9,10- dione derivatives as inhibitors of human telomerase
    • (c) Perry, P. J.; Gowan, S. M.; Reszka, A. P.; Polucci, P.; Jenkins, T. C.; Kelland, L. R.; Neidle, S. 1,4- and 2,6-disubstituted amidoanthracene-9,10- dione derivatives as inhibitors of human telomerase. J. Med. Chem. 1998, 41, 3253-3260.
    • (1998) J. Med. Chem , vol.41 , pp. 3253-3260
    • Perry, P.J.1    Gowan, S.M.2    Reszka, A.P.3    Polucci, P.4    Jenkins, T.C.5    Kelland, L.R.6    Neidle, S.7
  • 23
    • 0026776299 scopus 로고
    • Anthracene-9,10-diones as potential anticancer agents. Synthesis, DNA-binding, and biological studies on a series of 2,6-disubstituted derivatives
    • (e) Agbandje, M.; Jenkins, T. C.; McKenna, R.; Reszka, A. P.; Neidle, S. Anthracene-9,10-diones as potential anticancer agents. Synthesis, DNA-binding, and biological studies on a series of 2,6-disubstituted derivatives. J. Med. Chem. 1992, 35, 1418-1429.
    • (1992) J. Med. Chem , vol.35 , pp. 1418-1429
    • Agbandje, M.1    Jenkins, T.C.2    McKenna, R.3    Reszka, A.P.4    Neidle, S.5
  • 24
    • 38049007426 scopus 로고    scopus 로고
    • Zagotto, G.; Sissi, C.; Moro, S:.; Ben, D. D.; Parkinson, G. N.; Fox, K. R.; Neidle, S.; Palumbo, M. Amide bond direction modulates G-quadruplex recognition and telomerase inhibition by 2,6 and 2,7 bis-substituted anthracenedione derivatives. Bioorg. Med. Chem. 2008, 16, 354-361.
    • Zagotto, G.; Sissi, C.; Moro, S:.; Ben, D. D.; Parkinson, G. N.; Fox, K. R.; Neidle, S.; Palumbo, M. Amide bond direction modulates G-quadruplex recognition and telomerase inhibition by 2,6 and 2,7 bis-substituted anthracenedione derivatives. Bioorg. Med. Chem. 2008, 16, 354-361.
  • 25
    • 0038728819 scopus 로고    scopus 로고
    • Stability of intramolecular DNA quadruplexes: Comparison with DNA duplexes
    • (a) Risitano, A.; Fox, K. R. Stability of intramolecular DNA quadruplexes: comparison with DNA duplexes. Biochemistry. 2003, 42, 6507-6513.
    • (2003) Biochemistry , vol.42 , pp. 6507-6513
    • Risitano, A.1    Fox, K.R.2
  • 28
    • 0030743347 scopus 로고    scopus 로고
    • Advances in quantification and characterization of telomerase activity by the telomeric repeat amplification protocol (TRAP)
    • Kim, N. W.; Wu, F. Advances in quantification and characterization of telomerase activity by the telomeric repeat amplification protocol (TRAP). Nucleic Acids Res. 1997, 25, 2595-2597.
    • (1997) Nucleic Acids Res , vol.25 , pp. 2595-2597
    • Kim, N.W.1    Wu, F.2
  • 31
    • 0015153612 scopus 로고
    • Statistical thermodynamics of nucleic acid melting transitions with coupled binding equilibria
    • Crothers, D. M. Statistical thermodynamics of nucleic acid melting transitions with coupled binding equilibria. Biopolymers 1971, 10, 2147-2160.
    • (1971) Biopolymers , vol.10 , pp. 2147-2160
    • Crothers, D.M.1
  • 32
    • 0029761654 scopus 로고    scopus 로고
    • Peptidyl anthraquinones as potential antineoplastic drugs: Synthesis, DNA binding, redox cycling, and biological activity
    • Gatto, B.; Zagotto, G.; Sissi, C.; Cera, C.; Uriarte, E.; Palu, G.; Capranico, G.; Palumbo, M. Peptidyl anthraquinones as potential antineoplastic drugs: synthesis, DNA binding, redox cycling, and biological activity. J. Med. Chem. 1996, 39, 3114-3122.
    • (1996) J. Med. Chem , vol.39 , pp. 3114-3122
    • Gatto, B.1    Zagotto, G.2    Sissi, C.3    Cera, C.4    Uriarte, E.5    Palu, G.6    Capranico, G.7    Palumbo, M.8
  • 34
    • 50349102258 scopus 로고    scopus 로고
    • G-Quadruplex stabilizer 3,6-bis(1-methyl-4-vinyl pyridinium)carbazole diiodide induces accelerated senescence and inhibits tumorigenic properties in cancer cells
    • Huang, F.-C.; Chang, C.-C.; Lou, P.-J.; Kuo, I.; Chien, C.-W.; Chen, C.-T.; Shieh, F.-Y.; Chang, T.; Lin, J.-J. G-Quadruplex stabilizer 3,6-bis(1-methyl-4-vinyl pyridinium)carbazole diiodide induces accelerated senescence and inhibits tumorigenic properties in cancer cells. Mol. Cancer. Res. 2008, 6, OF1-OF10.
    • (2008) Mol. Cancer. Res , vol.6
    • Huang, F.-C.1    Chang, C.-C.2    Lou, P.-J.3    Kuo, I.4    Chien, C.-W.5    Chen, C.-T.6    Shieh, F.-Y.7    Chang, T.8    Lin, J.-J.9
  • 35
    • 20144369806 scopus 로고    scopus 로고
    • Highly prevalent putative quadruplex sequence motifs in human DNA
    • Todd, A. K.; Johnston, M.; Neidle, S. Highly prevalent putative quadruplex sequence motifs in human DNA. Nucleic Acids Res. 2005, 33, 2901-2907.
    • (2005) Nucleic Acids Res , vol.33 , pp. 2901-2907
    • Todd, A.K.1    Johnston, M.2    Neidle, S.3


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