메뉴 건너뛰기




Volumn 27, Issue 8, 2009, Pages 900-907

Molecular modeling of tricyclic compounds with anilino substituents and their intercalation complexes with DNA sequences

Author keywords

Acridines; DNA; Docking; Imidazo 4,5 b quinolines; Intercalation complexes; Thiazolo 5,4 b quinolines; Tricyclic compounds

Indexed keywords

BENZENE; BINDING ENERGY; CYTOTOXICITY; DNA; DOCKING; ELECTROSTATICS; INTERCALATION COMPOUNDS; MOLECULAR MODELING;

EID: 67349230449     PISSN: 10933263     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jmgm.2009.02.001     Document Type: Article
Times cited : (10)

References (37)
  • 1
    • 0023146095 scopus 로고
    • Footprinting at low temperatures: evidence that ethidium and other simple intercalators can discriminate between different nucleotide sequences
    • Fox K.R., and Waring M.J. Footprinting at low temperatures: evidence that ethidium and other simple intercalators can discriminate between different nucleotide sequences. Nucl. Acids Res. 15 (1987) 491-507
    • (1987) Nucl. Acids Res. , vol.15 , pp. 491-507
    • Fox, K.R.1    Waring, M.J.2
  • 2
    • 0032189683 scopus 로고    scopus 로고
    • Mechanism of action of eukaryotic DNA topoisomerase I and drugs targeted to the enzyme
    • Pommier Y., Pourquier P., Fan Y., and Strumberg D. Mechanism of action of eukaryotic DNA topoisomerase I and drugs targeted to the enzyme. Biochim. Biophys. Acta 1400 (1998) 83-105
    • (1998) Biochim. Biophys. Acta , vol.1400 , pp. 83-105
    • Pommier, Y.1    Pourquier, P.2    Fan, Y.3    Strumberg, D.4
  • 3
    • 0032190561 scopus 로고    scopus 로고
    • Mechanism of action of eukaryotic topoisomerase II and drugs targeted to the enzyme
    • Burden D.A., and Osheroff N. Mechanism of action of eukaryotic topoisomerase II and drugs targeted to the enzyme. Biochim. Biophys. Acta 1400 (1998) 139-154
    • (1998) Biochim. Biophys. Acta , vol.1400 , pp. 139-154
    • Burden, D.A.1    Osheroff, N.2
  • 4
    • 0004099105 scopus 로고
    • Foye W.O. (Ed), American Chemical Society, USA
    • Denny W.A. In: Foye W.O. (Ed). Cancer Chemotherapeutic Agents (1995), American Chemical Society, USA 218-239
    • (1995) Cancer Chemotherapeutic Agents , pp. 218-239
    • Denny, W.A.1
  • 5
    • 0021165002 scopus 로고
    • antitumor activity, and DNA binding properties of a new derivative of Amsacrine, N-5-Dimethyl-9-[(2-methoxy-4-methylsulfonylamino)phenylamino]-4-acridine carboxamide
    • Baguley B.C., Denny W.A., Atwell G.J., Finlay G.J., Rewcastle G.W., Twigden S.J., Wilson W.R., and Synthesis. antitumor activity, and DNA binding properties of a new derivative of Amsacrine, N-5-Dimethyl-9-[(2-methoxy-4-methylsulfonylamino)phenylamino]-4-acridine carboxamide. Cancer Res. 44 (1984) 3245-3251
    • (1984) Cancer Res. , vol.44 , pp. 3245-3251
    • Baguley, B.C.1    Denny, W.A.2    Atwell, G.J.3    Finlay, G.J.4    Rewcastle, G.W.5    Twigden, S.J.6    Wilson, W.R.7    Synthesis8
  • 6
    • 84986840475 scopus 로고
    • Specific molecular interactions of acridine drugs in complexes with topoisomerase II and DNA. SERS and resonance Raman study of m-AMSA in comparison with o-AMSA
    • Chourpa I., and Manfait M.J. Specific molecular interactions of acridine drugs in complexes with topoisomerase II and DNA. SERS and resonance Raman study of m-AMSA in comparison with o-AMSA. Raman Spectrosc. 26 (1995) 813-819
    • (1995) Raman Spectrosc. , vol.26 , pp. 813-819
    • Chourpa, I.1    Manfait, M.J.2
  • 7
    • 0030580353 scopus 로고    scopus 로고
    • Intracellular molecular interactions of antitumor drug amsacrine (m-AMSA) as revealed by surface-enhanced Raman spectroscopy
    • Chourpa I., Morjani H., Riou J.-F., and Manfait M. Intracellular molecular interactions of antitumor drug amsacrine (m-AMSA) as revealed by surface-enhanced Raman spectroscopy. FEBS Lett. 397 (1996) 61-64
    • (1996) FEBS Lett. , vol.397 , pp. 61-64
    • Chourpa, I.1    Morjani, H.2    Riou, J.-F.3    Manfait, M.4
  • 8
    • 0023715265 scopus 로고
    • DNA binding by epipodophyllotoxins and N-acyl anthracyclines: implications for mechanism of topoisomerase II inhibition
    • Chow K.-C., MacDonald T.L., and Ross W.E. DNA binding by epipodophyllotoxins and N-acyl anthracyclines: implications for mechanism of topoisomerase II inhibition. Mol. Pharmacol. 34 (1988) 467-473
    • (1988) Mol. Pharmacol. , vol.34 , pp. 467-473
    • Chow, K.-C.1    MacDonald, T.L.2    Ross, W.E.3
  • 9
    • 0034087037 scopus 로고    scopus 로고
    • Substituted benz[a]acridines and benz[c]acridines as mammalian topoisomerase poisons
    • Makhey D., Yu C., Liu A., Liu L.F., and La Voie E.J. Substituted benz[a]acridines and benz[c]acridines as mammalian topoisomerase poisons. Bioorg. Med. Chem. 8 (2000) 1171-1182
    • (2000) Bioorg. Med. Chem. , vol.8 , pp. 1171-1182
    • Makhey, D.1    Yu, C.2    Liu, A.3    Liu, L.F.4    La Voie, E.J.5
  • 12
    • 0023795194 scopus 로고
    • Development of a parenteral formulation for the antitumor agent acronycine
    • Dorr R.T., and Liddil J.D. Development of a parenteral formulation for the antitumor agent acronycine. J. Drug Dev. 1 (1988) 31-39
    • (1988) J. Drug Dev. , vol.1 , pp. 31-39
    • Dorr, R.T.1    Liddil, J.D.2
  • 15
    • 25444493351 scopus 로고    scopus 로고
    • Synthesis and anticancer evaluation of certain 4-anilinofuro[2,3-b]quinoline and 4-anilinofuro[3,2-c]quinoline derivatives
    • Chen Y.-L., Chen I.-L., Wang T.-C., Han C.-H., and Tzeng C.-C. Synthesis and anticancer evaluation of certain 4-anilinofuro[2,3-b]quinoline and 4-anilinofuro[3,2-c]quinoline derivatives. Eur. J. Med. Chem. 40 (2005) 928-934
    • (2005) Eur. J. Med. Chem. , vol.40 , pp. 928-934
    • Chen, Y.-L.1    Chen, I.-L.2    Wang, T.-C.3    Han, C.-H.4    Tzeng, C.-C.5
  • 16
    • 0032998857 scopus 로고    scopus 로고
    • A molecular modeling study of B-DNA-intercalation complexes with amsacrine and related 9-anilino-acridines
    • Fischer G., and Pindur U. A molecular modeling study of B-DNA-intercalation complexes with amsacrine and related 9-anilino-acridines. Pharmazie 54 (1999) 83-93
    • (1999) Pharmazie , vol.54 , pp. 83-93
    • Fischer, G.1    Pindur, U.2
  • 17
    • 33750631697 scopus 로고    scopus 로고
    • Unprecedented dual binding behaviour of acridine group of dye: a combined experimental and theoretical investigation for the development of anticancer chemotherapeutic agents
    • Rajendran A., and Nair B. Unprecedented dual binding behaviour of acridine group of dye: a combined experimental and theoretical investigation for the development of anticancer chemotherapeutic agents. Biochim. Biophys. Acta 1760 (2006) 1794-1801
    • (2006) Biochim. Biophys. Acta , vol.1760 , pp. 1794-1801
    • Rajendran, A.1    Nair, B.2
  • 18
    • 0029610425 scopus 로고
    • The experimental hardness and electronegativity of the purines and pyrimidines in DNA and RNA supported by the AM1 calculation of the electron affinities and ionization potentials
    • Zhang Q., and Chen E.C.M. The experimental hardness and electronegativity of the purines and pyrimidines in DNA and RNA supported by the AM1 calculation of the electron affinities and ionization potentials. Biochem. Biophys. Res. Commun. 217 (1995) 755-760
    • (1995) Biochem. Biophys. Res. Commun. , vol.217 , pp. 755-760
    • Zhang, Q.1    Chen, E.C.M.2
  • 19
    • 33747219381 scopus 로고    scopus 로고
    • Synthesis, cytotoxicity, QSAR, and intercalation study of new diindenopyridine derivatives
    • Miri R., Javidnia K., Sarkarzadeh H., and Hemmateenejad B. Synthesis, cytotoxicity, QSAR, and intercalation study of new diindenopyridine derivatives. Bioorg. Med. Chem. 14 (2006) 4842-4849
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 4842-4849
    • Miri, R.1    Javidnia, K.2    Sarkarzadeh, H.3    Hemmateenejad, B.4
  • 20
    • 37049135926 scopus 로고
    • Crystal and molecular structure of 4′-(acridin-9-ylamino) methanesulphonanilide hydrochloride, a compound showing antileukemic activity
    • Hall D., Swann D.A., and Waters T.N. Crystal and molecular structure of 4′-(acridin-9-ylamino) methanesulphonanilide hydrochloride, a compound showing antileukemic activity. J. Chem. Soc. Perkin Trans. II (1974) 1334-1337
    • (1974) J. Chem. Soc. Perkin Trans. II , pp. 1334-1337
    • Hall, D.1    Swann, D.A.2    Waters, T.N.3
  • 21
    • 0021084473 scopus 로고
    • Potential antitumor agents. 39. Anilino ring geometry of amsacrine and derivatives: relationship to DNA binding and antitumor activity
    • Denny W.A., Atwell G.J., and Baguley B.C. Potential antitumor agents. 39. Anilino ring geometry of amsacrine and derivatives: relationship to DNA binding and antitumor activity. J. Med. Chem. 26 (1983) 1625-1630
    • (1983) J. Med. Chem. , vol.26 , pp. 1625-1630
    • Denny, W.A.1    Atwell, G.J.2    Baguley, B.C.3
  • 22
    • 0028032864 scopus 로고
    • The purine 2-amino group as a critical recognition element for binding of small molecules to DNA
    • Waring M.J., and Bailly C. The purine 2-amino group as a critical recognition element for binding of small molecules to DNA. Gene 149 (1994) 69-79
    • (1994) Gene , vol.149 , pp. 69-79
    • Waring, M.J.1    Bailly, C.2
  • 23
    • 0000879582 scopus 로고    scopus 로고
    • Molecular modeling of intercalation complexes of antitumor active 9-aminoacridine and a [d,e]-anellated isoquinoline derivative with base paired deoxytetranucleotides
    • Rehn C., and Pindur U. Molecular modeling of intercalation complexes of antitumor active 9-aminoacridine and a [d,e]-anellated isoquinoline derivative with base paired deoxytetranucleotides. Monatsh. Chem. 127 (1996) 645-648
    • (1996) Monatsh. Chem. , vol.127 , pp. 645-648
    • Rehn, C.1    Pindur, U.2
  • 24
    • 0030710155 scopus 로고    scopus 로고
    • Electrostatic and non-electrostatic contributions to the binding free energies of anthracycline antibiotics to DNA
    • Baginski M., Fogolari F., and Briggs J.M. Electrostatic and non-electrostatic contributions to the binding free energies of anthracycline antibiotics to DNA. J. Mol. Biol. 274 (1997) 253-267
    • (1997) J. Mol. Biol. , vol.274 , pp. 253-267
    • Baginski, M.1    Fogolari, F.2    Briggs, J.M.3
  • 25
  • 26
    • 0031081360 scopus 로고    scopus 로고
    • Intercalation of ethidium and analogues with nucleic acids: a molecular orbital study
    • Patterson S., Coxon J., and Strekowski L. Intercalation of ethidium and analogues with nucleic acids: a molecular orbital study. Bioorg. Med. Chem. 5 (1997) 277-281
    • (1997) Bioorg. Med. Chem. , vol.5 , pp. 277-281
    • Patterson, S.1    Coxon, J.2    Strekowski, L.3
  • 27
    • 0025829187 scopus 로고
    • Interactions of anilinoacridines with nucleic acids: effects of substituent modifications on DNA-binding properties
    • Wadkins R.M., and Graves G.E. Interactions of anilinoacridines with nucleic acids: effects of substituent modifications on DNA-binding properties. Biochemistry 30 (1991) 4277-4283
    • (1991) Biochemistry , vol.30 , pp. 4277-4283
    • Wadkins, R.M.1    Graves, G.E.2
  • 28
    • 9644276941 scopus 로고    scopus 로고
    • Semiempirical study on the electronic structure of antitumor drugs ellipticines, olivacines and isoellipticines
    • Braga S., de Melo L., and Barone P. Semiempirical study on the electronic structure of antitumor drugs ellipticines, olivacines and isoellipticines. J. Mol. Struct. (Theochem.) 710 (2004) 51-59
    • (2004) J. Mol. Struct. (Theochem.) , vol.710 , pp. 51-59
    • Braga, S.1    de Melo, L.2    Barone, P.3
  • 29
    • 0027276685 scopus 로고
    • 2: rationale for sequence-specific Hoogsteen base pairing
    • 2: rationale for sequence-specific Hoogsteen base pairing. J. Med. Chem. 36 (1993) 1548-1561
    • (1993) J. Med. Chem. , vol.36 , pp. 1548-1561
    • Gallego, J.1    Ortiz, A.R.2    Gago, F.3
  • 30
    • 0031755316 scopus 로고    scopus 로고
    • Quantitative structure-activity relationships (QSAR) for 9-anilinoacridines: a comparative analysis
    • Gao H., Denny W.A., Garg R., and Hansch C. Quantitative structure-activity relationships (QSAR) for 9-anilinoacridines: a comparative analysis. Chem. Biol. Interact. 116 (1998) 157-180
    • (1998) Chem. Biol. Interact. , vol.116 , pp. 157-180
    • Gao, H.1    Denny, W.A.2    Garg, R.3    Hansch, C.4
  • 32
    • 0024599312 scopus 로고
    • Definitions and nomenclature of nucleic acid structure components
    • Dickerson R.E. Definitions and nomenclature of nucleic acid structure components. Nucleic Acids Res. 17 (1989) 1797-1803
    • (1989) Nucleic Acids Res. , vol.17 , pp. 1797-1803
    • Dickerson, R.E.1
  • 33
    • 0242396923 scopus 로고    scopus 로고
    • 3DNA: a software package for the analysis, rebuilding and visualization of three-dimensional nucleic acid structures
    • Lu X.-J., and Olson W.K. 3DNA: a software package for the analysis, rebuilding and visualization of three-dimensional nucleic acid structures. Nucleic Acids Res. 31 (2003) 5108-5121
    • (2003) Nucleic Acids Res. , vol.31 , pp. 5108-5121
    • Lu, X.-J.1    Olson, W.K.2
  • 35
    • 0035067134 scopus 로고    scopus 로고
    • BuildQSAR: A new computer program for QSAR studies
    • De Oliveira B.D., and Gáudio A.C. BuildQSAR: A new computer program for QSAR studies. Quant. Struct. -Act. Rel. 19 (2003) 599-601
    • (2003) Quant. Struct. -Act. Rel. , vol.19 , pp. 599-601
    • De Oliveira, B.D.1    Gáudio, A.C.2
  • 36
    • 0023895978 scopus 로고
    • Energetics and stereochemistry of DNA complexation with the antitumor AT specific intercalators tilorone and m-AMSA
    • Chen K., Gresh N., and Pullman B. Energetics and stereochemistry of DNA complexation with the antitumor AT specific intercalators tilorone and m-AMSA. Nucleic Acids Res. 16 (1988) 3061-3073
    • (1988) Nucleic Acids Res. , vol.16 , pp. 3061-3073
    • Chen, K.1    Gresh, N.2    Pullman, B.3
  • 37
    • 33748124430 scopus 로고    scopus 로고
    • Acenaphtho[1,2-b]pyrrole derivatives as new family of intercalators: Various DNA binding geometry and interesting antitumor capacity
    • Zhang Z., Yang Y., Zhang D., Wang Y., Qiana X., and Liu F. Acenaphtho[1,2-b]pyrrole derivatives as new family of intercalators: Various DNA binding geometry and interesting antitumor capacity. Bioorg. Med. Chem. 14 (2006) 6962-6970
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 6962-6970
    • Zhang, Z.1    Yang, Y.2    Zhang, D.3    Wang, Y.4    Qiana, X.5    Liu, F.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.