메뉴 건너뛰기




Volumn 79, Issue 12, 2010, Pages 1781-1790

Remarkable interference with telomeric function by a G-quadruplex selective bisantrene regioisomer

Author keywords

Alternative lengthening of telomeres; Bisantrene; G quadruplex; Telomerase; Telomere

Indexed keywords

ANTHRACENE DERIVATIVE; BISANTRENE; DNA; GUANINE QUADRUPLEX; NUCLEIC ACID; TELOMERASE;

EID: 77951297746     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2010.02.018     Document Type: Article
Times cited : (20)

References (49)
  • 1
    • 0022402513 scopus 로고
    • Identification of a specific telomere terminal transferase activity in Tetrahymena extracts
    • Greider C.W., Blackburn E.H. Identification of a specific telomere terminal transferase activity in Tetrahymena extracts. Cell 1985, 43:405-413.
    • (1985) Cell , vol.43 , pp. 405-413
    • Greider, C.W.1    Blackburn, E.H.2
  • 2
    • 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
  • 5
    • 24944460598 scopus 로고    scopus 로고
    • Shelterin: the protein complex that shapes and safeguards human telomeres
    • de Lange T. Shelterin: the protein complex that shapes and safeguards human telomeres. Genes Dev 2005, 19:2100-2110.
    • (2005) Genes Dev , vol.19 , pp. 2100-2110
    • de Lange, T.1
  • 6
    • 44349136891 scopus 로고    scopus 로고
    • Telomere dysfunction and tumour suppression: the senescence connection
    • Deng Y., Chan S.S., Chang S. Telomere dysfunction and tumour suppression: the senescence connection. Nat Rev Cancer 2008, 8:450-458.
    • (2008) Nat Rev Cancer , vol.8 , pp. 450-458
    • Deng, Y.1    Chan, S.S.2    Chang, S.3
  • 7
    • 66549124907 scopus 로고    scopus 로고
    • The structures of quadruplex nucleic acids and their drug complexes
    • Neidle S. The structures of quadruplex nucleic acids and their drug complexes. Curr Opin Struct Biol 2009, 19:239-250.
    • (2009) Curr Opin Struct Biol , vol.19 , pp. 239-250
    • Neidle, S.1
  • 9
    • 45749103733 scopus 로고    scopus 로고
    • Four-stranded nucleic acids: structure, function and targeting of G-quadruplexes
    • Huppert J.L. Four-stranded nucleic acids: structure, function and targeting of G-quadruplexes. Chem Soc Rev 2008, 37:1375-1384.
    • (2008) Chem Soc Rev , vol.37 , pp. 1375-1384
    • Huppert, J.L.1
  • 11
  • 12
    • 36049045013 scopus 로고    scopus 로고
    • Telomere damage induced by the G-quadruplex ligand RHPS4 has an antitumor effect
    • Salvati E., Leonetti C., Rizzo A., Scarsella M., Mottolese M., Galati R., et al. Telomere damage induced by the G-quadruplex ligand RHPS4 has an antitumor effect. J Clin Invest 2007, 117:3236-3247.
    • (2007) J Clin Invest , vol.117 , pp. 3236-3247
    • Salvati, E.1    Leonetti, C.2    Rizzo, A.3    Scarsella, M.4    Mottolese, M.5    Galati, R.6
  • 13
    • 7844223625 scopus 로고    scopus 로고
    • Human telomerase inhibition by regioisomeric disubstituted amidoanthracene-9,10-diones
    • Perry P.J., Reszka A.P., Wood A.A., Read M.A., Gowan S.M., Dosanjh H.S., et al. Human telomerase inhibition by regioisomeric disubstituted amidoanthracene-9,10-diones. J Med Chem 1998, 41:4873-4884.
    • (1998) J Med Chem , vol.41 , pp. 4873-4884
    • Perry, P.J.1    Reszka, A.P.2    Wood, A.A.3    Read, M.A.4    Gowan, S.M.5    Dosanjh, H.S.6
  • 14
    • 33846954426 scopus 로고    scopus 로고
    • Synthesis and human telomerase inhibition of a series of regioisomeric disubstituted amidoanthraquinones
    • Huang H.S., Chen I.B., Huang K.F., Lu W.C., Shieh F.Y., Huang Y.Y., et al. Synthesis and human telomerase inhibition of a series of regioisomeric disubstituted amidoanthraquinones. Chem Pharm Bull (Tokyo) 2007, 55:284-292.
    • (2007) Chem Pharm Bull (Tokyo) , vol.55 , pp. 284-292
    • Huang, H.S.1    Chen, I.B.2    Huang, K.F.3    Lu, W.C.4    Shieh, F.Y.5    Huang, Y.Y.6
  • 16
    • 0033566092 scopus 로고    scopus 로고
    • 2,7-Disubstituted amidofluorenone derivatives as inhibitors of human telomerase
    • Perry P.J., Read M.A., Davies R.T., Gowan S.M., Reszka A.P., Wood A.A., et al. 2,7-Disubstituted amidofluorenone derivatives as inhibitors of human telomerase. J Med Chem 1999, 42:2679-2684.
    • (1999) J Med Chem , vol.42 , pp. 2679-2684
    • Perry, P.J.1    Read, M.A.2    Davies, R.T.3    Gowan, S.M.4    Reszka, A.P.5    Wood, A.A.6
  • 18
    • 10744221442 scopus 로고    scopus 로고
    • Trisubstituted acridine derivatives as potent and selective telomerase inhibitors
    • Harrison R.J., Cuesta J., Chessari G., Read M.A., Basra S.K., Reszka A.P., et al. Trisubstituted acridine derivatives as potent and selective telomerase inhibitors. J Med Chem 2003, 46:4463-4476.
    • (2003) J Med Chem , vol.46 , pp. 4463-4476
    • Harrison, R.J.1    Cuesta, J.2    Chessari, G.3    Read, M.A.4    Basra, S.K.5    Reszka, A.P.6
  • 19
    • 0037022658 scopus 로고    scopus 로고
    • Cell senescence and telomere shortening induced by a new series of specific G-quadruplex DNA ligands
    • Riou J.F., Guittat L., Mailliet P., Laoui A., Renou E., Petitgenet O., et al. Cell senescence and telomere shortening induced by a new series of specific G-quadruplex DNA ligands. Proc Natl Acad Sci USA 2002, 99:2672-2677.
    • (2002) Proc Natl Acad Sci USA , vol.99 , pp. 2672-2677
    • Riou, J.F.1    Guittat, L.2    Mailliet, P.3    Laoui, A.4    Renou, E.5    Petitgenet, O.6
  • 20
    • 0033083378 scopus 로고    scopus 로고
    • Effects of cationic porphyrins as G-quadruplex interactive agents in human tumor cells
    • Izbicka E., Wheelhouse R.T., Raymond E., Davidson K.K., Lawrence R.A., Sun D., et al. Effects of cationic porphyrins as G-quadruplex interactive agents in human tumor cells. Cancer Res 1999, 59:639-644.
    • (1999) Cancer Res , vol.59 , pp. 639-644
    • Izbicka, E.1    Wheelhouse, R.T.2    Raymond, E.3    Davidson, K.K.4    Lawrence, R.A.5    Sun, D.6
  • 21
    • 0039129145 scopus 로고    scopus 로고
    • Accelerated assembly of G-quadruplex structures by a small molecule
    • Han H., Cliff C.L., Hurley L.H. Accelerated assembly of G-quadruplex structures by a small molecule. Biochemistry 1999, 38:6981-6986.
    • (1999) Biochemistry , vol.38 , pp. 6981-6986
    • Han, H.1    Cliff, C.L.2    Hurley, L.H.3
  • 22
    • 34249846802 scopus 로고    scopus 로고
    • Structure of the intramolecular human telomeric G-quadruplex in potassium solution: a novel adenine triple formation
    • Dai J., Punchihewa C., Ambrus A., Chen D., Jones R.A., Yang D. Structure of the intramolecular human telomeric G-quadruplex in potassium solution: a novel adenine triple formation. Nucleic Acids Res 2007, 35:2440-2450.
    • (2007) Nucleic Acids Res , vol.35 , pp. 2440-2450
    • Dai, J.1    Punchihewa, C.2    Ambrus, A.3    Chen, D.4    Jones, R.A.5    Yang, D.6
  • 23
    • 0032505178 scopus 로고    scopus 로고
    • Anthracene-9,10-diones as potential anticancer agents: bacterial mutation studies of amido-substituted derivatives reveal an unexpected lack of mutagenicity
    • Venitt S., Crofton-Sleigh C., Agbandje M., Jenkins T.C., Neidle S. Anthracene-9,10-diones as potential anticancer agents: bacterial mutation studies of amido-substituted derivatives reveal an unexpected lack of mutagenicity. J Med Chem 1998, 41:3748-3752.
    • (1998) J Med Chem , vol.41 , pp. 3748-3752
    • Venitt, S.1    Crofton-Sleigh, C.2    Agbandje, M.3    Jenkins, T.C.4    Neidle, S.5
  • 24
    • 0033524027 scopus 로고    scopus 로고
    • Molecular modeling studies on G-quadruplex complexes of telomerase inhibitors: structure-activity relationships
    • Read M.A., Wood A.A., Harrison J.R., Gowan S.M., Kelland L.R., Dosanjh H.S., et al. Molecular modeling studies on G-quadruplex complexes of telomerase inhibitors: structure-activity relationships. J Med Chem 1999, 42:4538-4546.
    • (1999) J Med Chem , vol.42 , pp. 4538-4546
    • Read, M.A.1    Wood, A.A.2    Harrison, J.R.3    Gowan, S.M.4    Kelland, L.R.5    Dosanjh, H.S.6
  • 25
    • 0024566242 scopus 로고
    • Interaction of bisantrene anti-cancer agents with DNA: footprinting, structural requirements for DNA unwinding, kinetics and mechanism of binding and correlation of structural and kinetic parameters with anti-cancer activity
    • Elliott J.A., Wilson W.D., Shea R.G., Hartley J.A., Reszka K., Lown J.W. Interaction of bisantrene anti-cancer agents with DNA: footprinting, structural requirements for DNA unwinding, kinetics and mechanism of binding and correlation of structural and kinetic parameters with anti-cancer activity. Anticancer Drug Des 1989, 3:271-282.
    • (1989) Anticancer Drug Des , vol.3 , pp. 271-282
    • Elliott, J.A.1    Wilson, W.D.2    Shea, R.G.3    Hartley, J.A.4    Reszka, K.5    Lown, J.W.6
  • 26
    • 0032557571 scopus 로고    scopus 로고
    • Mapping drug interactions at the covalent topoisomerase II-DNA complex by bisantrene/amsacrine congeners
    • Capranico G., Guano F., Moro S., Zagotto G., Sissi C., Gatto B., et al. Mapping drug interactions at the covalent topoisomerase II-DNA complex by bisantrene/amsacrine congeners. J Biol Chem 1998, 273:12732-12739.
    • (1998) J Biol Chem , vol.273 , pp. 12732-12739
    • Capranico, G.1    Guano, F.2    Moro, S.3    Zagotto, G.4    Sissi, C.5    Gatto, B.6
  • 27
    • 0032440043 scopus 로고    scopus 로고
    • DNA-binding preferences of bisantrene analogues: relevance to the sequence specificity of drug-mediated topoisomerase II poisoning
    • Sissi C., Bolgan L., Moro S., Zagotto G., Bailly C., Menta E., et al. DNA-binding preferences of bisantrene analogues: relevance to the sequence specificity of drug-mediated topoisomerase II poisoning. Mol Pharmacol 1998, 54:1036-1045.
    • (1998) Mol Pharmacol , vol.54 , pp. 1036-1045
    • Sissi, C.1    Bolgan, L.2    Moro, S.3    Zagotto, G.4    Bailly, C.5    Menta, E.6
  • 28
    • 0032548487 scopus 로고    scopus 로고
    • Synthesis, DNA-damaging and cytotoxic properties of novel topoisomerase II-directed bisantrene analogues
    • Zagotto G., Oliva A., Guano F., Menta E., Capranico G., Palumbo M. Synthesis, DNA-damaging and cytotoxic properties of novel topoisomerase II-directed bisantrene analogues. Bioorg Med Chem Lett 1998, 8:121-126.
    • (1998) Bioorg Med Chem Lett , vol.8 , pp. 121-126
    • Zagotto, G.1    Oliva, A.2    Guano, F.3    Menta, E.4    Capranico, G.5    Palumbo, M.6
  • 29
    • 0036832737 scopus 로고    scopus 로고
    • Telomere maintenance and cancer-look, no telomerase
    • Neumann A.A., Reddel R.R. Telomere maintenance and cancer-look, no telomerase. Nat Rev Cancer 2002, 2:879-884.
    • (2002) Nat Rev Cancer , vol.2 , pp. 879-884
    • Neumann, A.A.1    Reddel, R.R.2
  • 30
    • 33748989558 scopus 로고    scopus 로고
    • Telomere maintenance mechanisms in liposarcomas: association with histologic subtypes and disease progression
    • Costa A., Daidone M.G., Daprai L., Villa R., Cantu S., Pilotti S., et al. Telomere maintenance mechanisms in liposarcomas: association with histologic subtypes and disease progression. Cancer Res 2006, 66:8918-8924.
    • (2006) Cancer Res , vol.66 , pp. 8918-8924
    • Costa, A.1    Daidone, M.G.2    Daprai, L.3    Villa, R.4    Cantu, S.5    Pilotti, S.6
  • 31
    • 0016175370 scopus 로고
    • Theoretical aspects of DNA-protein interactions: co-operative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice
    • McGhee J.D., von Hippel P.H. Theoretical aspects of DNA-protein interactions: co-operative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice. J Mol Biol 1974, 86:469-489.
    • (1974) J Mol Biol , vol.86 , pp. 469-489
    • McGhee, J.D.1    von Hippel, P.H.2
  • 32
    • 33646943863 scopus 로고    scopus 로고
    • Human telomeric sequence forms a hybrid-type intramolecular G-quadruplex structure with mixed parallel/antiparallel strands in potassium solution
    • Ambrus A., Chen D., Dai J., Bialis T., Jones R.A., Yang D. Human telomeric sequence forms a hybrid-type intramolecular G-quadruplex structure with mixed parallel/antiparallel strands in potassium solution. Nucleic Acids Res 2006, 34:2723-2735.
    • (2006) Nucleic Acids Res , vol.34 , pp. 2723-2735
    • Ambrus, A.1    Chen, D.2    Dai, J.3    Bialis, T.4    Jones, R.A.5    Yang, D.6
  • 33
    • 28244469090 scopus 로고    scopus 로고
    • Regulation of growth arrest in senescence: telomere damage is not the end of the story
    • Herbig U., Sedivy J.M. Regulation of growth arrest in senescence: telomere damage is not the end of the story. Mech Ageing Dev 2006, 127:16-24.
    • (2006) Mech Ageing Dev , vol.127 , pp. 16-24
    • Herbig, U.1    Sedivy, J.M.2
  • 35
    • 0032514479 scopus 로고    scopus 로고
    • 1,4- and 2,6-disubstituted amidoanthracene-9,10-dione derivatives as inhibitors of human telomerase
    • Perry P.J., Gowan S.M., Reszka A.P., Polucci P., Jenkins T.C., Kelland L.R., et al. 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
  • 36
    • 0038155211 scopus 로고    scopus 로고
    • Activation of human telomerase reverse transcriptase expression by some new symmetrical bis-substituted derivatives of the anthraquinone
    • Huang H.S., Chiou J.F., Fong Y., Hou C.C., Lu Y.C., Wang J.Y., et al. Activation of human telomerase reverse transcriptase expression by some new symmetrical bis-substituted derivatives of the anthraquinone. J Med Chem 2003, 46:3300-3307.
    • (2003) J Med Chem , vol.46 , pp. 3300-3307
    • Huang, H.S.1    Chiou, J.F.2    Fong, Y.3    Hou, C.C.4    Lu, Y.C.5    Wang, J.Y.6
  • 37
    • 47549098577 scopus 로고    scopus 로고
    • Synthesis, human telomerase inhibition and anti-proliferative studies of a series of 2,7-bis-substituted amido-anthraquinone derivatives
    • Huang H.S., Huang K.F., Li C.L., Huang Y.Y., Chiang Y.H., Huang F.C., et al. Synthesis, human telomerase inhibition and anti-proliferative studies of a series of 2,7-bis-substituted amido-anthraquinone derivatives. Bioorg Med Chem 2008, 16:6976-6986.
    • (2008) Bioorg Med Chem , vol.16 , pp. 6976-6986
    • Huang, H.S.1    Huang, K.F.2    Li, C.L.3    Huang, Y.Y.4    Chiang, Y.H.5    Huang, F.C.6
  • 38
    • 13444311877 scopus 로고    scopus 로고
    • Human telomerase inhibition and cytotoxicity of regioisomeric disubstituted amidoanthraquinones and aminoanthraquinones
    • Huang H.S., Chou C.L., Guo C.L., Yuan C.L., Lu Y.C., Shieh F.Y., et al. Human telomerase inhibition and cytotoxicity of regioisomeric disubstituted amidoanthraquinones and aminoanthraquinones. Bioorg Med Chem 2005, 13:1435-1444.
    • (2005) Bioorg Med Chem , vol.13 , pp. 1435-1444
    • Huang, H.S.1    Chou, C.L.2    Guo, C.L.3    Yuan, C.L.4    Lu, Y.C.5    Shieh, F.Y.6
  • 39
    • 0036152654 scopus 로고    scopus 로고
    • Molecular modelling and cytotoxicity of substituted anthraquinones as inhibitors of human telomerase
    • Cairns D., Michalitsi E., Jenkins T.C., Mackay S.P. Molecular modelling and cytotoxicity of substituted anthraquinones as inhibitors of human telomerase. Bioorg Med Chem 2002, 10:803-807.
    • (2002) Bioorg Med Chem , vol.10 , pp. 803-807
    • Cairns, D.1    Michalitsi, E.2    Jenkins, T.C.3    Mackay, S.P.4
  • 40
    • 7044249456 scopus 로고    scopus 로고
    • Evaluation of by disubstituted acridone derivatives as telomerase inhibitors: the importance of G-quadruplex binding
    • Harrison R.J., Reszka A.P., Haider S.M., Romagnoli B., Morrell J., Read M.A., et al. Evaluation of by disubstituted acridone derivatives as telomerase inhibitors: the importance of G-quadruplex binding. Bioorg Med Chem Lett 2004, 14:5845-5849.
    • (2004) Bioorg Med Chem Lett , vol.14 , pp. 5845-5849
    • Harrison, R.J.1    Reszka, A.P.2    Haider, S.M.3    Romagnoli, B.4    Morrell, J.5    Read, M.A.6
  • 41
    • 67749103504 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of novel 4,5-bis(dialkylaminoalkyl)-substituted acridines as potent telomeric G-quadruplex ligands
    • Laronze-Cochard M., Kim Y.M., Brassart B., Riou J.F., Laronze J.Y., Sapi J. Synthesis and biological evaluation of novel 4,5-bis(dialkylaminoalkyl)-substituted acridines as potent telomeric G-quadruplex ligands. Eur J Med Chem 2009, 44:3880-3888.
    • (2009) Eur J Med Chem , vol.44 , pp. 3880-3888
    • Laronze-Cochard, M.1    Kim, Y.M.2    Brassart, B.3    Riou, J.F.4    Laronze, J.Y.5    Sapi, J.6
  • 43
    • 58149318660 scopus 로고
    • 1D and 2D 1H NMR studies on bisantrene complexes with short DNA oligomers
    • Yao S., Wilson W.D. 1D and 2D 1H NMR studies on bisantrene complexes with short DNA oligomers. Sci China B 1995, 38:1462-1472.
    • (1995) Sci China B , vol.38 , pp. 1462-1472
    • Yao, S.1    Wilson, W.D.2
  • 44
    • 0034578478 scopus 로고    scopus 로고
    • G-quadruplexes as therapeutic targets
    • Neidle S., Read M.A. G-quadruplexes as therapeutic targets. Biopolymers 2000, 56:195-208.
    • (2000) Biopolymers , vol.56 , pp. 195-208
    • Neidle, S.1    Read, M.A.2
  • 45
    • 44349142304 scopus 로고    scopus 로고
    • Structural basis of DNA quadruplex recognition by an acridine drug
    • Campbell N.H., Parkinson G.N., Reszka A.P., Neidle S. Structural basis of DNA quadruplex recognition by an acridine drug. J Am Chem Soc 2008, 130:6722-6724.
    • (2008) J Am Chem Soc , vol.130 , pp. 6722-6724
    • Campbell, N.H.1    Parkinson, G.N.2    Reszka, A.P.3    Neidle, S.4
  • 46
    • 70349084987 scopus 로고    scopus 로고
    • The G-quadruplex ligand telomestatin impairs binding of topoisomerase IIIalpha to G-quadruplex-forming oligonucleotides and uncaps telomeres in ALT cells
    • Temime-Smaali N., Guittat L., Sidibe A., Shin-ya K., Trentesaux C., Riou J.F. The G-quadruplex ligand telomestatin impairs binding of topoisomerase IIIalpha to G-quadruplex-forming oligonucleotides and uncaps telomeres in ALT cells. PLoS One 2009, 4:e6919.
    • (2009) PLoS One , vol.4
    • Temime-Smaali, N.1    Guittat, L.2    Sidibe, A.3    Shin-ya, K.4    Trentesaux, C.5    Riou, J.F.6
  • 48
    • 0034760505 scopus 로고    scopus 로고
    • Potent inhibition of telomerase by small-molecule pentacyclic acridines capable of interacting with G-quadruplexes
    • Gowan S.M., Heald R., Stevens M.F., Kelland L.R. Potent inhibition of telomerase by small-molecule pentacyclic acridines capable of interacting with G-quadruplexes. Mol Pharmacol 2001, 60:981-988.
    • (2001) Mol Pharmacol , vol.60 , pp. 981-988
    • Gowan, S.M.1    Heald, R.2    Stevens, M.F.3    Kelland, L.R.4
  • 49
    • 0037434540 scopus 로고    scopus 로고
    • Design, synthesis, and biological evaluation of a series of fluoroquinoanthroxazines with contrasting dual mechanisms of action against topoisomerase II and G-quadruplexes
    • Kim M.Y., Duan W., Gleason-Guzman M., Hurley L.H. Design, synthesis, and biological evaluation of a series of fluoroquinoanthroxazines with contrasting dual mechanisms of action against topoisomerase II and G-quadruplexes. J Med Chem 2003, 46:571-583.
    • (2003) J Med Chem , vol.46 , pp. 571-583
    • Kim, M.Y.1    Duan, W.2    Gleason-Guzman, M.3    Hurley, L.H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.