메뉴 건너뛰기




Volumn 18, Issue 11, 2013, Pages 14228-14240

Targeting C-myc G-quadruplex: Dual recognition by aminosugar- bisbenzimidazoles with varying linker lengths

Author keywords

C myc; FID; G quadruplex; Hoechst 33258; Neomycin; Oncogenes

Indexed keywords

GUANINE QUADRUPLEX; MYC PROTEIN; NEOMYCIN; NUCLEIC ACID; PIBENZIMOL;

EID: 84888609795     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules181114228     Document Type: Article
Times cited : (35)

References (44)
  • 1
    • 33846928449 scopus 로고    scopus 로고
    • G-quadruplexes in promoters throughout the human genome
    • Huppert, J.L.; Balasubramanian, S. G-quadruplexes in promoters throughout the human genome. Nucleic Acids Res. 2007, 35, 406-413.
    • (2007) Nucleic Acids Res. , vol.35 , pp. 406-413
    • Huppert, J.L.1    Balasubramanian, S.2
  • 2
    • 84865974713 scopus 로고    scopus 로고
    • G4 motifs in human genes
    • Maizels, N. G4 motifs in human genes. Ann. N. Y. Acad. Sci. 2012, 1267, 53-60.
    • (2012) Ann. N. Y. Acad. Sci. , vol.1267 , pp. 53-60
    • Maizels, N.1
  • 3
    • 55249087006 scopus 로고    scopus 로고
    • A thermodynamic overview of naturally occurring intramolecular DNA quadruplexes
    • Kumar, N.; Maiti, S. A thermodynamic overview of naturally occurring intramolecular DNA quadruplexes. Nucleic Acids Res. 2008, 36, 5610-5622.
    • (2008) Nucleic Acids Res. , vol.36 , pp. 5610-5622
    • Kumar, N.1    Maiti, S.2
  • 4
    • 0025877846 scopus 로고
    • Inhibition of telomerase by G-quartet DNA structures
    • Zahler, A.M.; Williamson, J.R.; Cech, T.R.; Prescott, D.M. Inhibition of telomerase by G-quartet DNA structures. Nature 1991, 350, 718-720.
    • (1991) Nature , vol.350 , pp. 718-720
    • Zahler, A.M.1    Williamson, J.R.2    Cech, T.R.3    Prescott, D.M.4
  • 5
    • 84876976986 scopus 로고    scopus 로고
    • Novel anticancer therapeutics targeting telomerase
    • Ruden, M.; Puri, N. Novel anticancer therapeutics targeting telomerase. Cancer Treat. Rev. 2013, 39, 444-456.
    • (2013) Cancer Treat. Rev. , vol.39 , pp. 444-456
    • Ruden, M.1    Puri, N.2
  • 6
    • 67649833785 scopus 로고    scopus 로고
    • G-quadruplex nucleic acids as therapeutic targets
    • Balasubramanian, S.; Neidle, S. G-quadruplex nucleic acids as therapeutic targets. Curr. Opin. Chem. Biol. 2009, 13, 345-353.
    • (2009) Curr. Opin. Chem. Biol. , vol.13 , pp. 345-353
    • Balasubramanian, S.1    Neidle, S.2
  • 7
    • 79953313413 scopus 로고    scopus 로고
    • Targeting G-quadruplexes in gene promoters: A novel anticancer strategy? Nat
    • Balasubramanian, S.; Hurley, L.H.; Neidle, S. Targeting G-quadruplexes in gene promoters: A novel anticancer strategy? Nat. Rev. Drug Discov. 2011, 10, 261-275.
    • (2011) Rev. Drug Discov. , vol.10 , pp. 261-275
    • Balasubramanian, S.1    Hurley, L.H.2    Neidle, S.3
  • 9
    • 33745849998 scopus 로고    scopus 로고
    • The structure and function of telomerase reverse transcriptase
    • Autexier, C.; Lue, N.F. The structure and function of telomerase reverse transcriptase. Annu. Rev. Biochem. 2006, 75, 493-517.
    • (2006) Annu. Rev. Biochem. , vol.75 , pp. 493-517
    • Autexier, C.1    Lue, N.F.2
  • 10
    • 84875464903 scopus 로고    scopus 로고
    • Quantitative visualization of DNA G-quadruplex structures in human cells
    • Biffi, G.; Tannahill, D.; McCafferty, J.; Balasubramanian, S. Quantitative visualization of DNA G-quadruplex structures in human cells. Nat. Chem. 2013, 5, 182-186.
    • (2013) Nat. Chem. , vol.5 , pp. 182-186
    • Biffi, G.1    Tannahill, D.2    McCafferty, J.3    Balasubramanian, S.4
  • 11
    • 84877768759 scopus 로고    scopus 로고
    • G-quadruplex structures are stable and detectable in human genomic DNA
    • doi:10.1038/ncomms2792
    • Lam, E.Y.N.; Beraldi, D.; Tannahill, D.; Balasubramanian, S. G-quadruplex structures are stable and detectable in human genomic DNA. Nat. Commun. 2013, doi:10.1038/ncomms2792.
    • (2013) Nat. Commun.
    • Lam, E.Y.N.1    Beraldi, D.2    Tannahill, D.3    Balasubramanian, S.4
  • 12
    • 79952344184 scopus 로고    scopus 로고
    • Evidence of the formation of G-quadruplex structures in the promoter region of the human vascular endothelial growth factor gene
    • Sun, D.; Guo, K.; Shin, Y. Evidence of the formation of G-quadruplex structures in the promoter region of the human vascular endothelial growth factor gene. Nucleic Acids Res. 2011, 39, 1256-1265.
    • (2011) Nucleic Acids Res. , vol.39 , pp. 1256-1265
    • Sun, D.1    Guo, K.2    Shin, Y.3
  • 13
    • 84888592974 scopus 로고    scopus 로고
    • Telomeric quadruplex ligands I: Anthraquinones and acridines
    • Neidle, S., Ed.; Academic Press: Boston, MA, USA
    • Telomeric Quadruplex Ligands I: Anthraquinones and acridines. In Therapeutic Applications of Quadruplex Nucleic Acids; Neidle, S., Ed.; Academic Press: Boston, MA, USA, 2012; pp. 67-91.
    • (2012) Therapeutic Applications of Quadruplex Nucleic Acids , pp. 67-91
  • 14
    • 39049147645 scopus 로고    scopus 로고
    • A hitchhiker's guide to G-quadruplex ligands
    • 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
  • 15
    • 0033541133 scopus 로고    scopus 로고
    • Intercalative G-tetraplex stabilization of telomeric DNA by a cationic porphyrin
    • Haq, I.; Trent, J.O.; Chowdhry, B.Z.; Jenkins, T.C. Intercalative G-tetraplex stabilization of telomeric DNA by a cationic porphyrin. J. Am. Chem. Soc. 1999, 121, 1768-1779.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 1768-1779
    • Haq, I.1    Trent, J.O.2    Chowdhry, B.Z.3    Jenkins, T.C.4
  • 16
  • 17
    • 0037060042 scopus 로고    scopus 로고
    • Perylene diimide G-quadruplex DNA binding selectivity is mediated by ligand aggregation
    • Kerwin, S.M.; Chen, G.; Kern, J.T.; Thomas, P.W. Perylene diimide G-quadruplex DNA binding selectivity is mediated by ligand aggregation. Bioorg. Med. Chem. Lett. 2002, 12, 447-450.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 447-450
    • Kerwin, S.M.1    Chen, G.2    Kern, J.T.3    Thomas, P.W.4
  • 18
    • 0037119783 scopus 로고    scopus 로고
    • Perylene diimides with different side chains are selective in inducing different G-quadruplex DNA structures and in inhibiting telomerase
    • Rossetti, L.; Franceschin, M.; Bianco, A.; Ortaggi, G.; Savino, M. Perylene diimides with different side chains are selective in inducing different G-quadruplex DNA structures and in inhibiting telomerase. Bioorg. Med. Chem. Lett. 2002, 12, 2527-2533.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 2527-2533
    • Rossetti, L.1    Franceschin, M.2    Bianco, A.3    Ortaggi, G.4    Savino, M.5
  • 19
    • 84859904419 scopus 로고    scopus 로고
    • Disubstituted 1,8-dipyrazolcarbazole derivatives as a new type of C-myc G-quadruplex binding ligands
    • Chen, W.; Zhou, C.; Yao, P.; Wang, X.; Tan, J.; Li, D.; Ou, T.; Gu, L.; Huang, Z. Disubstituted 1,8-dipyrazolcarbazole derivatives as a new type of C-myc G-quadruplex binding ligands. Bioorg. Med. Chem. 2012, 20, 2829-2836.
    • (2012) Bioorg. Med. Chem. , vol.20 , pp. 2829-2836
    • Chen, W.1    Zhou, C.2    Yao, P.3    Wang, X.4    Tan, J.5    Li, D.6    Ou, T.7    Gu, L.8    Huang, Z.9
  • 20
    • 84861625962 scopus 로고    scopus 로고
    • 12-n-Methylated 5,6-dihydrobenzo[c]acridine derivatives: A new class of highly selective ligands for C-myc G-quadruplex DNA
    • Liao, S.; Zhou, C.; Wu, W.; Ou, T.; Tan, J.; Li, D.; Gu, L.; Huang, Z. 12-n-Methylated 5,6-dihydrobenzo[c]acridine derivatives: A new class of highly selective ligands for C-myc G-quadruplex DNA. Eur. J. Med. Chem. 2012, 53, 52-63.
    • (2012) Eur. J. Med. Chem. , vol.53 , pp. 52-63
    • Liao, S.1    Zhou, C.2    Wu, W.3    Ou, T.4    Tan, J.5    Li, D.6    Gu, L.7    Huang, Z.8
  • 21
    • 79955065928 scopus 로고    scopus 로고
    • Structure-based optimization of FDA-approved drug methylene blue as a C-myc G-quadruplex DNA stabilizer
    • Chan, D.S.; Yang, H.; Kwan, M.H.; Cheng, Z.; Lee, P.; Bai, L.; Jiang, Z.; Wong, C.; Fong, W.; Leung, C.; et al. Structure-based optimization of FDA-approved drug methylene blue as a C-myc G-quadruplex DNA stabilizer. Biochimie 2011, 93, 1055-1064.
    • (2011) Biochimie , vol.93 , pp. 1055-1064
    • Chan, D.S.1    Yang, H.2    Kwan, M.H.3    Cheng, Z.4    Lee, P.5    Bai, L.6    Jiang, Z.7    Wong, C.8    Fong, W.9    Leung, C.10
  • 22
    • 77953901414 scopus 로고    scopus 로고
    • Identification of natural product fonsecin B as a stabilizing ligand of C-myc G-quadruplex DNA by high-throughput virtual screening
    • Lee, H.; Chan, D.S.; Yang, F.; Lam, H.; Yan, S.; Che, C.; Ma, D.; Leung, C. Identification of natural product fonsecin B as a stabilizing ligand of C-myc G-quadruplex DNA by high-throughput virtual screening. Chem. Commun. 2010, 46, 4680-4682.
    • (2010) Chem. Commun. , vol.46 , pp. 4680-4682
    • Lee, H.1    Chan, D.S.2    Yang, F.3    Lam, H.4    Yan, S.5    Che, C.6    Ma, D.7    Leung, C.8
  • 23
    • 84865091468 scopus 로고    scopus 로고
    • In silico screening of quadruplex-binding ligands
    • Ma, D.; Ma, V.P.; Chan, D.S.; Leung, K.; Zhong, H.; Leung, C. In silico screening of quadruplex-binding ligands. Methods 2012, 57, 106-114.
    • (2012) Methods , vol.57 , pp. 106-114
    • Ma, D.1    Ma, V.P.2    Chan, D.S.3    Leung, K.4    Zhong, H.5    Leung, C.6
  • 24
    • 0141458938 scopus 로고    scopus 로고
    • Hoechst 33258 binds to G-quadruplex in the promoter region of human C-myc
    • Maiti, S.; Chaudhury, N.K.; Chowdhury, S. Hoechst 33258 binds to G-quadruplex in the promoter region of human C-myc. Biochem. Biophys. Res. Commun. 2003, 310, 505-512.
    • (2003) Biochem. Biophys. Res. Commun. , vol.310 , pp. 505-512
    • Maiti, S.1    Chaudhury, N.K.2    Chowdhury, S.3
  • 27
    • 47149091638 scopus 로고    scopus 로고
    • Molecular recognition of a DNA:RNA hybrid: Sub-nanomolar binding by a neomycin-methidium conjugate
    • Shaw, N.N.; Xi, H.; Arya, D.P. Molecular recognition of a DNA:RNA hybrid: Sub-nanomolar binding by a neomycin-methidium conjugate. Bioorg. Med. Chem. Lett. 2008, 18, 4142-4145.
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 4142-4145
    • Shaw, N.N.1    Xi, H.2    Arya, D.P.3
  • 28
    • 0141919831 scopus 로고    scopus 로고
    • Reaching into the major groove of b-DNA: Synthesis and nucleic acid binding of a neomycin-hoechst 33258 conjugate
    • Arya, D.P.; Willis, B. Reaching into the major groove of b-DNA: Synthesis and nucleic acid binding of a neomycin-hoechst 33258 conjugate. J. Am. Chem. Soc. 2003, 125, 12398-12399.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12398-12399
    • Arya, D.P.1    Willis, B.2
  • 29
    • 79955927721 scopus 로고    scopus 로고
    • Neomycin-neomycin dimer: An all-carbohydrate scaffold with high affinity for AT-rich DNA duplexes
    • Kumar, S.; Xue, L.; Arya, D.P. Neomycin-neomycin dimer: An all-carbohydrate scaffold with high affinity for AT-rich DNA duplexes. J. Am. Chem. Soc. 2011, 133, 7361-7375.
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 7361-7375
    • Kumar, S.1    Xue, L.2    Arya, D.P.3
  • 30
    • 33748672701 scopus 로고    scopus 로고
    • Recognition of b-DNA by neomycin-Hoechst 33258 conjugates
    • Willis, B.; Arya, D.P. Recognition of b-DNA by neomycin-Hoechst 33258 conjugates. Biochemistry 2006, 45, 10217-10232.
    • (2006) Biochemistry , vol.45 , pp. 10217-10232
    • Willis, B.1    Arya, D.P.2
  • 31
    • 79953706621 scopus 로고    scopus 로고
    • Synthesis and spectroscopic studies of the aminoglycoside (neomycin)-perylene conjugate binding to human telomeric DNA
    • Xue, L.; Ranjan, N.; Arya, D.P. Synthesis and spectroscopic studies of the aminoglycoside (neomycin)-perylene conjugate binding to human telomeric DNA. Biochemistry 2011, 50, 2838-2849.
    • (2011) Biochemistry , vol.50 , pp. 2838-2849
    • Xue, L.1    Ranjan, N.2    Arya, D.P.3
  • 32
    • 79960914931 scopus 로고    scopus 로고
    • Recognition of HIV TAR RNA by triazole linked neomycin dimers
    • Kumar, S.; Arya, D.P. Recognition of HIV TAR RNA by triazole linked neomycin dimers. Bioorg. Med. Chem. Lett. 2011, 21, 4788-4792.
    • (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 4788-4792
    • Kumar, S.1    Arya, D.P.2
  • 33
    • 84878646999 scopus 로고    scopus 로고
    • Dual recognition of the human telomeric G-quadruplex by a neomycin-anthraquinone conjugate
    • Ranjan, N.; Davis, E.; Xue, L.; Arya, D.P. Dual recognition of the human telomeric G-quadruplex by a neomycin-anthraquinone conjugate. Chem. Commun. 2013, 49, 5796-5798.
    • (2013) Chem. Commun. , vol.49 , pp. 5796-5798
    • Ranjan, N.1    Davis, E.2    Xue, L.3    Arya, D.P.4
  • 34
    • 84872382324 scopus 로고    scopus 로고
    • Aminoglycosylation can enhance the G-quadruplex binding activity of epigallocatechin
    • Bai, L.; Ho, H.; Ma, D.; Yang, H.; Fu, W.; Jiang, Z. Aminoglycosylation can enhance the G-quadruplex binding activity of epigallocatechin. PLoS One 2013, 8, e53962.
    • (2013) PLoS One , vol.8
    • Bai, L.1    Ho, H.2    Ma, D.3    Yang, H.4    Fu, W.5    Jiang, Z.6
  • 35
    • 84877762172 scopus 로고    scopus 로고
    • Existence of G-quadruplex structures in promoter region of oncogenes confirmed by G-quadruplex DNA cross-linking strategy
    • doi:10.1038/srep01811
    • Yuan, L.; Tian, T.; Chen, Y.; Yan, S.; Xing, X.; Zhang, Z.; Zhai, Q.; Xu, L.; Wang, S.; Weng, X.; et al. Existence of G-quadruplex structures in promoter region of oncogenes confirmed by G-quadruplex DNA cross-linking strategy. Sci. Rep. 2013, doi:10.1038/srep01811.
    • (2013) Sci. Rep.
    • Yuan, L.1    Tian, T.2    Chen, Y.3    Yan, S.4    Xing, X.5    Zhang, Z.6    Zhai, Q.7    Xu, L.8    Wang, S.9    Weng, X.10
  • 37
    • 0034833710 scopus 로고    scopus 로고
    • A simple, high-resolution method for establishing DNA binding affinity and sequence selectivity
    • Boger, D.L.; Fink, B.E.; Brunette, S.R.; Tse, W.C.; Hedrick, M.P. A simple, high-resolution method for establishing DNA binding affinity and sequence selectivity. J. Am. Chem. Soc. 2001, 123, 5878-5891.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 5878-5891
    • Boger, D.L.1    Fink, B.E.2    Brunette, S.R.3    Tse, W.C.4    Hedrick, M.P.5
  • 38
    • 0034641332 scopus 로고    scopus 로고
    • Total synthesis of distamycin A and 2640 analogues: A solution-phase combinatorial approach to the discovery of new, bioactive DNA binding agents and development of a rapid, high-throughput screen for determining relative DNA binding affinity or DNA binding sequence selectivity
    • Boger, D.L.; Fink, B.E.; Hedrick, M.P. Total synthesis of distamycin A and 2640 analogues: A solution-phase combinatorial approach to the discovery of new, bioactive DNA binding agents and development of a rapid, high-throughput screen for determining relative DNA binding affinity or DNA binding sequence selectivity. J. Am. Chem. Soc. 2000, 122, 6382-6394.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 6382-6394
    • Boger, D.L.1    Fink, B.E.2    Hedrick, M.P.3
  • 39
    • 33746809014 scopus 로고    scopus 로고
    • Development of a fluorescent intercalator displacement assay (G4-FID) for establishing quadruplex-DNA affinity and selectivity of putative ligands
    • Monchaud, D.; Allain, C.; Teulade-Fichou, M. Development of a fluorescent intercalator displacement assay (G4-FID) for establishing quadruplex-DNA affinity and selectivity of putative ligands. Bioorg. Med. Chem. Lett. 2006, 16, 4842-4845.
    • (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 4842-4845
    • Monchaud, D.1    Allain, C.2    Teulade-Fichou, M.3
  • 40
    • 80055014243 scopus 로고    scopus 로고
    • Thermodynamics of nucleic acid "shape Readout" by an aminosugar
    • Xi, H.; Davis, E.; Ranjan, N.; Xue, L.; Hyde-Volpe, D.; Arya, D.P. Thermodynamics of nucleic acid "Shape Readout" by an aminosugar. Biochemistry 2011, 50, 9088-9113.
    • (2011) Biochemistry , vol.50 , pp. 9088-9113
    • Xi, H.1    Davis, E.2    Ranjan, N.3    Xue, L.4    Hyde-Volpe, D.5    Arya, D.P.6
  • 41
    • 77951023778 scopus 로고    scopus 로고
    • Calorimetric and spectroscopic studies of aminoglycoside binding to AT-rich DNA triple helices
    • Xi, H.; Kumar, S.; Dosen-Micovic, L.; Arya, D.P. Calorimetric and spectroscopic studies of aminoglycoside binding to AT-rich DNA triple helices. Biochimie 2010, 92, 514-529.
    • (2010) Biochimie , vol.92 , pp. 514-529
    • Xi, H.1    Kumar, S.2    Dosen-Micovic, L.3    Arya, D.P.4
  • 42
    • 27144440078 scopus 로고    scopus 로고
    • Thermal difference spectra: A specific signature for nucleic acid structures
    • Mergny, J.L.; Li, J.; Lacroix, L.; Amrane, S.; Chaires, J.B. Thermal difference spectra: A specific signature for nucleic acid structures. Nucleic Acids Res. 2005, 33, e138/1-e138/6.
    • (2005) Nucleic Acids Res. , vol.33
    • Mergny, J.L.1    Li, J.2    Lacroix, L.3    Amrane, S.4    Chaires, J.B.5
  • 44
    • 0034833770 scopus 로고    scopus 로고
    • Aminoglycoside-nucleic acid interactions: Remarkable stabilization of DNA and RNA triple helices by neomycin
    • Arya, D.P.; Coffee, R.L., Jr.; Willis, B.; Abramovitch, A.I. Aminoglycoside-nucleic acid interactions: remarkable stabilization of DNA and RNA triple helices by neomycin. J. Am. Chem. Soc. 2001, 123, 5385-5395.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 5385-5395
    • Arya, D.P.1    Coffee Jr., R.L.2    Willis, B.3    Abramovitch, A.I.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.