메뉴 건너뛰기




Volumn 18, Issue 11, 2013, Pages 13446-13470

Xanthene and xanthone derivatives as G-quadruplex stabilizing ligands

Author keywords

Bcl 2; C myc; ESI MS; FRET; G quadruplex; Telomere; Xanthene; Xanthone

Indexed keywords

GUANINE QUADRUPLEX; MYC PROTEIN; PROTEIN BCL 2; XANTHENE DERIVATIVE; XANTHONE; XANTHONE DERIVATIVE;

EID: 84888632242     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules181113446     Document Type: Article
Times cited : (16)

References (48)
  • 2
    • 66149087629 scopus 로고    scopus 로고
    • G-quadruplex DNA structures and organic chemistry: More than one connection
    • Franceschin, M. G-quadruplex DNA structures and organic chemistry: More than one connection. Eur. J. Org. Chem. 2009, 2009, 2225-2238.
    • (2009) Eur. J. Org. Chem. , vol.2009 , pp. 2225-2238
    • Franceschin, M.1
  • 4
    • 84857038475 scopus 로고    scopus 로고
    • Specific binding of telomeric G-quadruplexes by hydrosoluble perylene derivatives inhibits repeat addition processivity of human telomerase
    • D'Ambrosio, D.; Reichenbach, P.; Micheli, E.; Alvino, A.; Franceschin, M.; Savino, M.; Lingner, J. Specific binding of telomeric G-quadruplexes by hydrosoluble perylene derivatives inhibits repeat addition processivity of human telomerase. Biochemie 2012, 94, 854-863.
    • (2012) Biochemie , vol.94 , pp. 854-863
    • D'ambrosio, D.1    Reichenbach, P.2    Micheli, E.3    Alvino, A.4    Franceschin, M.5    Savino, M.6    Lingner, J.7
  • 5
    • 79960840968 scopus 로고    scopus 로고
    • Binding properties of human telomeric quadruplex multimers: A new route for drug design
    • Cummaro, A.; Fottichia, I.; Franceschin, M.; Giancola, C.; Petraccone, L. Binding properties of human telomeric quadruplex multimers: A new route for drug design. Biochemie 2011, 93, 1392-1400.
    • (2011) Biochemie , vol.93 , pp. 1392-1400
    • Cummaro, A.1    Fottichia, I.2    Franceschin, M.3    Giancola, C.4    Petraccone, L.5
  • 6
    • 77949884776 scopus 로고    scopus 로고
    • Water soluble cationic perylene derivatives as possible telomerase inhibitors: The search for selective G-quadruplex targeting
    • Micheli, E.; D'Ambrosio, D.; Franceschin, M.; Savino, M. Water soluble cationic perylene derivatives as possible telomerase inhibitors: The search for selective G-quadruplex targeting. Mini-Rev. Med. Chem. 2009, 9, 1622-1632.
    • (2009) Mini-Rev. Med. Chem. , vol.9 , pp. 1622-1632
    • Micheli, E.1    D'ambrosio, D.2    Franceschin, M.3    Savino, M.4
  • 7
    • 10644290098 scopus 로고    scopus 로고
    • Selective interactions of perylene derivatives having different side chains with inter-and intramolecular G-quadruplex structures A correlation with telomerase inhibition
    • Rossetti, L.; Franceschin, M.; Schirripa, S.; Bianco, A.; Ortaggi, G.; Savino, M. Selective interactions of perylene derivatives having different side chains with inter-and intramolecular G-quadruplex structures. A correlation with telomerase inhibition. Bioorg. Med. Chem. Lett. 2005, 15, 413-420.
    • (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 413-420
    • Rossetti, L.1    Franceschin, M.2    Schirripa, S.3    Bianco, A.4    Ortaggi, G.5    Savino, M.6
  • 8
    • 57849150849 scopus 로고    scopus 로고
    • Stabilisation of G-Quadruplex DNA by small molecules
    • Arola, A.; Ramon, V. Stabilisation of G-Quadruplex DNA by small molecules. Curr. Top. Med. Chem. 2008, 15, 1405-1415.
    • (2008) Curr. Top. Med. Chem. , vol.15 , pp. 1405-1415
    • Arola, A.1    Ramon, V.2
  • 10
    • 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.; 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
  • 13
    • 46649106069 scopus 로고    scopus 로고
    • TRAP-LIG, a modified telomere repeat amplification protocol assay to quantitate telomerase inhibition by small molecules
    • Reed, J.; Gunaratnam, M.; Beltran, M.; Reszka, A.P.; Vilar, R.; Neidle, S. TRAP-LIG, a modified telomere repeat amplification protocol assay to quantitate telomerase inhibition by small molecules. Anal. Biochem. 2008, 390, 99-105.
    • (2008) Anal. Biochem. , vol.390 , pp. 99-105
    • Reed, J.1    Gunaratnam, M.2    Beltran, M.3    Reszka, A.P.4    Vilar, R.5    Neidle, S.6
  • 14
    • 84881587908 scopus 로고    scopus 로고
    • Biological activities and bioavailability of mangosteen xanthones: A critical review of the current evidence
    • Gutierrez-Orozco, F.; Failla, M.L. Biological activities and bioavailability of mangosteen xanthones: A critical review of the current evidence. Nutrients 2013, 13, 3163-3183.
    • (2013) Nutrients , vol.13 , pp. 3163-3183
    • Gutierrez-Orozco, F.1    Failla, M.L.2
  • 16
    • 67650459178 scopus 로고    scopus 로고
    • A hydrophilic three side-chained triazatruxene as a new strong and selective G-quadruplex ligand
    • Ginnari-Satriani, L.; Casagrande, V.; Bianco, A.; Ortaggi, G.; Franceschin, M. A hydrophilic three side-chained triazatruxene as a new strong and selective G-quadruplex ligand. Org. Biomol. Chem. 2009, 7, 2513-2516.
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 2513-2516
    • Ginnari-Satriani, L.1    Casagrande, V.2    Bianco, A.3    Ortaggi, G.4    Franceschin, M.5
  • 18
    • 33847785752 scopus 로고    scopus 로고
    • Specific interactions with intra-and intermolecular G-quadruplex DNA structures by hydrosoluble coronene derivatives: A new class of telomerase inhibitors
    • Franceschin, M.; Alvino, A.; Casagrande, V.; Mauriello, C.; Pascucci, E.; Savino, M.; Ortaggi, G.; Bianco, A. Specific interactions with intra-and intermolecular G-quadruplex DNA structures by hydrosoluble coronene derivatives: A new class of telomerase inhibitors. Bioorg. Med. Chem. 2007, 15, 1848-1858.
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 1848-1858
    • Franceschin, M.1    Alvino, A.2    Casagrande, V.3    Mauriello, C.4    Pascucci, E.5    Savino, M.6    Ortaggi, G.7    Bianco, A.8
  • 19
    • 84860116133 scopus 로고    scopus 로고
    • Experimental Methods for studying the interactions between G-Quadruplex structures and ligands
    • Jaumot, J.; Gargallo, R. Experimental Methods for studying the interactions between G-Quadruplex structures and ligands. Curr. Pharm. Des. 2012, 14, 1900-1916.
    • (2012) Curr. Pharm. Des. , vol.14 , pp. 1900-1916
    • Jaumot, J.1    Gargallo, R.2
  • 20
    • 80055021268 scopus 로고    scopus 로고
    • Methods for investigating G-quadruplex DNA/ligand interactions
    • Murat, P.; Singh, Y.; Defrancq, E. Methods for investigating G-quadruplex DNA/ligand interactions. Chem. Soc. Rev. 2011, 40, 5293-5307.
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 5293-5307
    • Murat, P.1    Singh, Y.2    Defrancq, E.3
  • 21
    • 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
  • 23
    • 11644261806 scopus 로고    scopus 로고
    • Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function
    • Morris, G.M.; Goodsell, D.S.; Halliday, R.S.; Huey, R.; Hart, W.E.; Belew, R.K.; Olson, A.J. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J. Comput. Chem. 1998, 19, 1639-1662.
    • (1998) J. Comput. Chem. , vol.19 , pp. 1639-1662
    • Morris, G.M.1    Goodsell, D.S.2    Halliday, R.S.3    Huey, R.4    Hart, W.E.5    Belew, R.K.6    Olson, A.J.7
  • 24
    • 70450158916 scopus 로고    scopus 로고
    • Tandem application of virtual screening and NMR experiments in the discovery of brand new DNA quadruplex groove binders
    • Cosconati, S.; Marinelli, L.; Trotta, R.; Virno, A.; Mayol, L.; Novellino, E.; Olson, A.J.; Randazzo, A. Tandem application of virtual screening and NMR experiments in the discovery of brand new DNA quadruplex groove binders. J. Am. Chem. Soc. 2009, 131, 16336-16337.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 16336-16337
    • Cosconati, S.1    Marinelli, L.2    Trotta, R.3    Virno, A.4    Mayol, L.5    Novellino, E.6    Olson, A.J.7    Randazzo, A.8
  • 26
    • 0037142071 scopus 로고    scopus 로고
    • Crystal structure of parallel quadruplexes from human telomeric DNA
    • Parkinson, G.N.; Lee, M.P.; Neidle, S. Crystal structure of parallel quadruplexes from human telomeric DNA. Nature 2002, 417, 876-880.
    • (2002) Nature , vol.417 , pp. 876-880
    • Parkinson, G.N.1    Lee, M.P.2    Neidle, S.3
  • 27
    • 84884921116 scopus 로고    scopus 로고
    • Small-molecule G-quadruplex interactions: Systematic exploration of conformational space using multiple molecular dynamics
    • Husby, J.; Todd, A.K.; Platts, J.A.; Neidle, S. Small-molecule G-quadruplex interactions: Systematic exploration of conformational space using multiple molecular dynamics. Biopolymers 2013, 99, 989-1005.
    • (2013) Biopolymers , vol.99 , pp. 989-1005
    • Husby, J.1    Todd, A.K.2    Platts, J.A.3    Neidle, S.4
  • 30
    • 40749091190 scopus 로고    scopus 로고
    • The number and distances of positive charges of polyamine side chains in a series of perylene diimides significantly influence their ability to induce Gquadruplex structures and inhibit human telomerase
    • Franceschin, M.; Lombardo, C.M.; Pascucci, E.; D'Ambrosio, D.; Micheli, E.; Bianco, A.; Ortaggi, G.; Savino, M. The number and distances of positive charges of polyamine side chains in a series of perylene diimides significantly influence their ability to induce Gquadruplex structures and inhibit human telomerase. Bioorg. Med. Chem. 2008, 16, 2292-2304.
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 2292-2304
    • Franceschin, M.1    Lombardo, C.M.2    Pascucci, E.3    D'ambrosio, D.4    Micheli, E.5    Bianco, A.6    Ortaggi, G.7    Savino, M.8
  • 31
    • 67649647842 scopus 로고    scopus 로고
    • Selective G-quadruplex ligands: The significant role of side chain charge density in a series of perylene derivatives
    • Micheli, E.; Lombardo, C.M.; D'Ambrosio, D.; Franceschin, M.; Neidle, S.; Savino, M. Selective G-quadruplex ligands: The significant role of side chain charge density in a series of perylene derivatives. Bioorg. Med. Chem. Lett. 2009, 19, 3903-3908.
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 3903-3908
    • Micheli, E.1    Lombardo, C.M.2    D'ambrosio, D.3    Franceschin, M.4    Neidle, S.5    Savino, M.6
  • 33
    • 33947713244 scopus 로고    scopus 로고
    • New highly hydrosoluble and not self-aggregated perylene derivatives with three and four polar side chains as G-quadruplex telomere targeting agents and telomerase inhibitors
    • Franceschin, M.; Pascucci, E.; Alvino, A.; D'Ambrosio, D.; Bianco, A.; Ortaggi, G.; Savino, M. New highly hydrosoluble and not self-aggregated perylene derivatives with three and four polar side chains as G-quadruplex telomere targeting agents and telomerase inhibitors. Bioorg. Med. Chem. Lett. 2007, 17, 2515-2522.
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 2515-2522
    • Franceschin, M.1    Pascucci, E.2    Alvino, A.3    D'ambrosio, D.4    Bianco, A.5    Ortaggi, G.6    Savino, M.7
  • 34
    • 7244233013 scopus 로고    scopus 로고
    • Rational design of novel photoinduced electron transfer type fluorescent probes for sodium cation
    • Kenmoku, S.; Urano, Y.; Kanda, K.; Kojima, H.; Kikuchi, K.; Nagano, T. Rational design of novel photoinduced electron transfer type fluorescent probes for sodium cation. Tetrahedron 2004, 60, 11067-11074.
    • (2004) Tetrahedron , vol.60 , pp. 11067-11074
    • Kenmoku, S.1    Urano, Y.2    Kanda, K.3    Kojima, H.4    Kikuchi, K.5    Nagano, T.6
  • 35
    • 0033404871 scopus 로고    scopus 로고
    • Interaction between antitumor drugs and a double-stranded oligonucleotide studied by electrospray ionization mass spectrometry
    • Gabelica, V.; de Pauw, E.; Rosu, F. Interaction between antitumor drugs and a double-stranded oligonucleotide studied by electrospray ionization mass spectrometry. J. Mass Spectrom. 1999, 34, 1328-1337.
    • (1999) J. Mass Spectrom. , vol.34 , pp. 1328-1337
    • Gabelica, V.1    De Pauw, E.2    Rosu, F.3
  • 36
    • 0034096809 scopus 로고    scopus 로고
    • Gas phase thermal denaturation of an oligonucleotide duplex and its complexes with minor groove binders
    • Gabelica, V.; Rosu, F.; Houssier, C.; de Pauw, E. Gas phase thermal denaturation of an oligonucleotide duplex and its complexes with minor groove binders. Rapid Comm. Mass Spectrom. 2000, 14, 464-467.
    • (2000) Rapid Comm. Mass Spectrom. , vol.14 , pp. 464-467
    • Gabelica, V.1    Rosu, F.2    Houssier, C.3    De Pauw, E.4
  • 37
    • 0036376018 scopus 로고    scopus 로고
    • Triplex and quadruplex DNA structures studied by electrospray mass spectrometry
    • Rosu, F.; Gabelica, V.; Houssier, C.; Colson, P.; de Pauw, E. Triplex and quadruplex DNA structures studied by electrospray mass spectrometry. Rapid Comm. Mass Spectrom. 2002, 16, 1729-1736.
    • (2002) Rapid Comm. Mass Spectrom. , vol.16 , pp. 1729-1736
    • Rosu, F.1    Gabelica, V.2    Houssier, C.3    Colson, P.4    De Pauw, E.5
  • 38
    • 45949111852 scopus 로고    scopus 로고
    • Electrospray mass spectrometry to study drug-nucleic acids interactions
    • Rosu, F.; de Pauw, E.; Gabelica, V. Electrospray mass spectrometry to study drug-nucleic acids interactions. Biochemie 2008, 90, 1074-1087.
    • (2008) Biochemie , vol.90 , pp. 1074-1087
    • Rosu, F.1    De Pauw, E.2    Gabelica, V.3
  • 40
    • 65649130074 scopus 로고    scopus 로고
    • Study of binding affinity and selectivity of perylene and coronene derivatives towards duplex and quadruplex DNA by ESI-MS
    • Casagrande, V.; Alvino, A.; Bianco, A.; Ortaggi, G.; Franceschin, M. Study of binding affinity and selectivity of perylene and coronene derivatives towards duplex and quadruplex DNA by ESI-MS. J. Mass Spectrom. 2009, 4, 530-540.
    • (2009) J. Mass Spectrom. , vol.4 , pp. 530-540
    • Casagrande, V.1    Alvino, A.2    Bianco, A.3    Ortaggi, G.4    Franceschin, M.5
  • 43
    • 84870275680 scopus 로고    scopus 로고
    • Aromatic core extension in the series of N-cyclic bay-substituted perylene G-quadruplex ligands: Increased telomere damage, antitumor activity, and strong selectivity for neoplastic over healthy cells
    • Franceschin, M.; Rizzo, A.; Casagrande, V.; Salvati, E.; Alvino, A.; Altieri, A.; Ciammaichella, A.; Iachettini, S.; Leonetti, C.; Ortaggi, G.;. Aromatic core extension in the series of N-cyclic bay-substituted perylene G-quadruplex ligands: Increased telomere damage, antitumor activity, and strong selectivity for neoplastic over healthy cells. Chem. Med. Chem. 2012, 7, 2144-2154.
    • (2012) Chem. Med. Chem. , vol.7 , pp. 2144-2154
    • Franceschin, M.1    Rizzo, A.2    Casagrande, V.3    Salvati, E.4    Alvino, A.5    Altieri, A.6    Ciammaichella, A.7    Iachettini, S.8    Leonetti, C.9    Ortaggi, G.10
  • 44
    • 2342568938 scopus 로고    scopus 로고
    • Synthesis and evaluation of analogues of 10H-indolo[3,2-b]quinoline as G-quadruplex stabilising ligands and potential inhibitors of the enzyme telomerase
    • Guyen, B.; Schultes, C.M.; Hazel, P.; Mann, J.; Neidle, S. Synthesis and evaluation of analogues of 10H-indolo[3,2-b]quinoline as G-quadruplex stabilising ligands and potential inhibitors of the enzyme telomerase. Org. Biomol. Chem. 2004, 2, 981-988.
    • (2004) Org. Biomol. Chem. , vol.2 , pp. 981-988
    • Guyen, B.1    Schultes, C.M.2    Hazel, P.3    Mann, J.4    Neidle, S.5
  • 45
    • 0033397980 scopus 로고    scopus 로고
    • Python: A programming language for software integration and development
    • Sanner, M.F. Python: A programming language for software integration and development. J. Mol. Graphics Mod. 1999, 17, 57-61.
    • (1999) J. Mol. Graphics Mod. , vol.17 , pp. 57-61
    • Sanner, M.F.1
  • 46
    • 79960591542 scopus 로고    scopus 로고
    • Synthesis of a dibromoperylene phosphoramidite building block and its incorporation at the 5' end of a G-quadruplex forming oligonucleotide: Spectroscopic properties and structuralstudies of the resulting dibromoperylene conjugate
    • Franceschin, M.; Borbone, N.; Oliviero, G.; Casagrande, V.; Scuotto, M.; Coppola, T.; Borioni, S.; Mayol, L.; Ortaggi. G.; Bianco A.; et al. Synthesis of a dibromoperylene phosphoramidite building block and its incorporation at the 5' end of a G-quadruplex forming oligonucleotide: Spectroscopic properties and structuralstudies of the resulting dibromoperylene conjugate. Bioconjug Chem. 2011, 22, 1309-1319.
    • (2011) Bioconjug Chem , vol.22 , pp. 1309-1319
    • Franceschin, M.1    Borbone, N.2    Oliviero, G.3    Casagrande, V.4    Scuotto, M.5    Coppola, T.6    Borioni, S.7    Mayol, L.8    Ortaggi, G.9    Bianco, A.10


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.