메뉴 건너뛰기




Volumn 14, Issue 5, 1999, Pages 433-442

A DNA binding indolocarbazole disaccharide derivative remains highly cytotoxic without inhibiting topoisomerase I

Author keywords

Anti cancer drugs; Cytotoxicity; DNA binding; Indolocarbazole; Rebeccamycin; Topoisomerase I

Indexed keywords

6 FORMYLAMINO 12,13 DIHYDRO 1,11 DIHYDROXY 5H INDOLO[2,3 A][PYRROLO[3,4 C]CARBAZOLE 5,7(6H) DIONE 13 GLUCOSIDE; CARBAZOLE DERIVATIVE; DNA; DNA TOPOISOMERASE; DNA TOPOISOMERASE (ATP HYDROLYSING); GLUCOSE; MALTOSE;

EID: 0033497816     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (11)

References (40)
  • 1
    • 9844260513 scopus 로고    scopus 로고
    • Syntheses and biological activity (topoisomerases inhibition, antitumoral and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moieties and substituted on the imide nitrogen with a methyl group
    • Anizon F., Belin L., Moreau P., Sancelme M., Voldoire A., Prudhomme M., Ollier M., Sevère D., Riou J.F., Bailly C., Fabro D., Meyer T. (1997) Syntheses and biological activity (topoisomerases inhibition, antitumoral and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moieties and substituted on the imide nitrogen with a methyl group. Journal of Medicinal Chemistry, 40, 3456.
    • (1997) Journal of Medicinal Chemistry , vol.40 , pp. 3456
    • Anizon, F.1    Belin, L.2    Moreau, P.3    Sancelme, M.4    Voldoire, A.5    Prudhomme, M.6    Ollier, M.7    Sevère, D.8    Riou, J.F.9    Bailly, C.10    Fabro, D.11    Meyer, T.12
  • 4
    • 0028905348 scopus 로고
    • Novel indolocarbazole compound 6-N-formylamino-12,13-dihydro-1, 11-dihydroxy-13-(β-D-glucopyranosyl)-5H-indolo[2,3-a]pyrrolo-[3,4-c] carbazole-5,7-(6H)-dione (NB-506): Its potent antitumor activities in mice
    • Arakawa H., Iguchi T., Morita M., Yoshinari T., Kojiri K., Suda H., Okura A., Nishimura S. (1995) Novel indolocarbazole compound 6-N-formylamino-12,13-dihydro-1, 11-dihydroxy-13-(β-D-glucopyranosyl)-5H-indolo[2,3-a]pyrrolo-[3,4-c] carbazole-5,7-(6H)-dione (NB-506): its potent antitumor activities in mice. Cancer Research, 55, 1316.
    • (1995) Cancer Research , vol.55 , pp. 1316
    • Arakawa, H.1    Iguchi, T.2    Morita, M.3    Yoshinari, T.4    Kojiri, K.5    Suda, H.6    Okura, A.7    Nishimura, S.8
  • 7
    • 0028899328 scopus 로고
    • Comparison of different footprinting methodologies for detecting binding sites for a small ligand on DNA
    • Bailly C., Waring M.J. (1995) Comparison of different footprinting methodologies for detecting binding sites for a small ligand on DNA. Journal of Biomolecular Structure and Dynamics, 12, 869.
    • (1995) Journal of Biomolecular Structure and Dynamics , vol.12 , pp. 869
    • Bailly, C.1    Waring, M.J.2
  • 9
  • 11
    • 0033133944 scopus 로고    scopus 로고
    • Calories from carbohydrates. Energetic contribution of the carbohydrate moiety of rebeccamycin to DNA binding and the effect of its orientation on topoisomerase I inhibition
    • Bailly C., Qu X., Graves D.E., Prudhomme M., Chaires J.B. (1999b) Calories from carbohydrates. Energetic contribution of the carbohydrate moiety of rebeccamycin to DNA binding and the effect of its orientation on topoisomerase I inhibition. Chemistry & Biology, 6, 277.
    • (1999) Chemistry & Biology , vol.6 , pp. 277
    • Bailly, C.1    Qu, X.2    Graves, D.E.3    Prudhomme, M.4    Chaires, J.B.5
  • 12
    • 0033049569 scopus 로고    scopus 로고
    • Enhanced binding to DNA and topoisomerase I inhibition by an analog of the antitumor antibiotic rebeccamycin containing an amino-sugar residue
    • Bailly C., Qu X., Anizon F., Prudhomme M., Riou J.F., Chaires J.B. (1999c) Enhanced binding to DNA and topoisomerase I inhibition by an analog of the antitumor antibiotic rebeccamycin containing an amino-sugar residue. Molecular Pharmacology, 55, 377.
    • (1999) Molecular Pharmacology , vol.55 , pp. 377
    • Bailly, C.1    Qu, X.2    Anizon, F.3    Prudhomme, M.4    Riou, J.F.5    Chaires, J.B.6
  • 13
    • 0033614922 scopus 로고    scopus 로고
    • Substitution at the F-ring N-imide of the indolocarbazole antitumor drug NB-506 increases the cytotoxicity, DNA binding and topoisomerase I inhibition activities
    • Bailly C., Qu X., Chaires J.B., Colson P., Houssier C., Ohkubo M., Nishimura S., Yoshinari T. (1999d) Substitution at the F-ring N-imide of the indolocarbazole antitumor drug NB-506 increases the cytotoxicity, DNA binding and topoisomerase I inhibition activities. Journal of Medicinal Chemistry, 42, 2927.
    • (1999) Journal of Medicinal Chemistry , vol.42 , pp. 2927
    • Bailly, C.1    Qu, X.2    Chaires, J.B.3    Colson, P.4    Houssier, C.5    Ohkubo, M.6    Nishimura, S.7    Yoshinari, T.8
  • 14
    • 0030465221 scopus 로고    scopus 로고
    • Dissecting the free energy of drug binding to DNA
    • Chaires J.B. (1996) Dissecting the free energy of drug binding to DNA. Anti-Cancer Drug Design, 11, 569.
    • (1996) Anti-Cancer Drug Design , vol.11 , pp. 569
    • Chaires, J.B.1
  • 15
    • 0027295656 scopus 로고
    • Dissection of the free energy of anthracycline antibiotic binding to DNA: Electrostatic contributions
    • Chaires J.B., Priebe W., Graves D.E., Burke T.G. (1993) Dissection of the free energy of anthracycline antibiotic binding to DNA: electrostatic contributions. Journal of the American Chemical Society, 115, 5360.
    • (1993) Journal of the American Chemical Society , vol.115 , pp. 5360
    • Chaires, J.B.1    Priebe, W.2    Graves, D.E.3    Burke, T.G.4
  • 16
    • 0028099438 scopus 로고
    • Inhibition of topoisomerase I by anthracycline antibiotics: Evidence for general inhibition of topoisomerase I by DNA binding agents
    • Crow R.T., Crothers D.M. (1994) Inhibition of topoisomerase I by anthracycline antibiotics: evidence for general inhibition of topoisomerase I by DNA binding agents. Journal of Medicinal Chemistry, 37, 3191.
    • (1994) Journal of Medicinal Chemistry , vol.37 , pp. 3191
    • Crow, R.T.1    Crothers, D.M.2
  • 17
    • 0021689084 scopus 로고
    • Polyelectrolyte effects on site-binding equilibria with application to the intercalation of drugs into DNA
    • Friedman R.A., Manning G.S. (1984) Polyelectrolyte effects on site-binding equilibria with application to the intercalation of drugs into DNA. Biopolymers, 23, 2671.
    • (1984) Biopolymers , vol.23 , pp. 2671
    • Friedman, R.A.1    Manning, G.S.2
  • 18
    • 0021799944 scopus 로고
    • Action of camptothecin and its derivatives on deoxyribonucleic acid
    • Fukada M. (1985) Action of camptothecin and its derivatives on deoxyribonucleic acid. Biochemical Pharmacology, 34, 1225.
    • (1985) Biochemical Pharmacology , vol.34 , pp. 1225
    • Fukada, M.1
  • 21
    • 0029035461 scopus 로고
    • Antitumor activities of a new indolocarbazole substance, NB-506, and establishment of NB-506-resistant cell lines, SBC-3/NB
    • Kanzawa F., Nishio K., Kubota N., Saijo N. (1995) Antitumor activities of a new indolocarbazole substance, NB-506, and establishment of NB-506-resistant cell lines, SBC-3/NB. Cancer Research, 55, 2806.
    • (1995) Cancer Research , vol.55 , pp. 2806
    • Kanzawa, F.1    Nishio, K.2    Kubota, N.3    Saijo, N.4
  • 30
    • 0017820499 scopus 로고
    • Thermodynamic analysis of ion effects on the binding and conformational equilibria of proteins and nucleic acids: The role of ion association or release, screening, and ion effects on water activity
    • Record M.T., Anderson C.F., Lohman T.M. (1978) Thermodynamic analysis of ion effects on the binding and conformational equilibria of proteins and nucleic acids: the role of ion association or release, screening, and ion effects on water activity. Quarterly Review of Biophysics, 11, 103.
    • (1978) Quarterly Review of Biophysics , vol.11 , pp. 103
    • Record, M.T.1    Anderson, C.F.2    Lohman, T.M.3
  • 31
    • 0000714445 scopus 로고    scopus 로고
    • Structure-activity relationships in a series of substituted indolocarbazoles: Topoisomerase I and protein kinase C inhibition and antitumoral and antimicrobial properties
    • Rodrigues-Pereira E., Belin L., Sancelme M., Prudhomme M., Ollier M., Rapp M., Servère D., Riou J.F., Fabbro D. (1996) Structure-activity relationships in a series of substituted indolocarbazoles: topoisomerase I and protein kinase C inhibition and antitumoral and antimicrobial properties. Journal of Medicinal Chemistry, 39, 4471.
    • (1996) Journal of Medicinal Chemistry , vol.39 , pp. 4471
    • Rodrigues-Pereira, E.1    Belin, L.2    Sancelme, M.3    Prudhomme, M.4    Ollier, M.5    Rapp, M.6    Servère, D.7    Riou, J.F.8    Fabbro, D.9
  • 33
    • 0031965431 scopus 로고    scopus 로고
    • New chemotherapeutic agents for the treatment of non-small cell lung cancer
    • Saijo N. (1998) New chemotherapeutic agents for the treatment of non-small cell lung cancer. Chest, 113, 17S.
    • (1998) Chest , vol.113
    • Saijo, N.1
  • 36
    • 0031297095 scopus 로고    scopus 로고
    • Cellular determinants of resistance to indolocarbazole analogue NB-506. A novel potent topoisomerase I inhibitor, in multidrug-resistant human tumor cells
    • Vanhoefer U., Voigt W., Hilger R.A., Yin M.-B., Harstrick A., Seeber S., Rustum Y.M. (1997) Cellular determinants of resistance to indolocarbazole analogue NB-506. A novel potent topoisomerase I inhibitor, in multidrug-resistant human tumor cells. Oncology Research, 9, 485.
    • (1997) Oncology Research , vol.9 , pp. 485
    • Vanhoefer, U.1    Voigt, W.2    Hilger, R.A.3    Yin, M.-B.4    Harstrick, A.5    Seeber, S.6    Rustum, Y.M.7
  • 37
    • 0029974583 scopus 로고    scopus 로고
    • Bisindolyl-maleimides linked to DNA minor groove binding lexitropsins: Synthesis, inhibitory activity against topoisomerase I, and biological evaluation
    • Xie G., Gupta R., Atchison K., Lown J.W. (1996) Bisindolyl-maleimides linked to DNA minor groove binding lexitropsins: synthesis, inhibitory activity against topoisomerase I, and biological evaluation. Journal of Medicinal Chemistry, 39, 1049.
    • (1996) Journal of Medicinal Chemistry , vol.39 , pp. 1049
    • Xie, G.1    Gupta, R.2    Atchison, K.3    Lown, J.W.4
  • 38
    • 0026678588 scopus 로고
    • Induction of mammalian DNA topoisomerase I mediated DNA cleavage by antitumor indolocarbazole derivatives
    • Yamashita Y., Fujii N., Murakata C., Ashizawa T., Okabe M., Nakano H. (1992) Induction of mammalian DNA topoisomerase I mediated DNA cleavage by antitumor indolocarbazole derivatives. Biochemistry, 31, 12069.
    • (1992) Biochemistry , vol.31 , pp. 12069
    • Yamashita, Y.1    Fujii, N.2    Murakata, C.3    Ashizawa, T.4    Okabe, M.5    Nakano, H.6
  • 40
    • 0028931509 scopus 로고
    • Novel antitumor indolocarbazole compound 6-N-formyl-amino-12,13-dihydro-1,11-dihydroxy-13-(β-D-glucopyranosyl)-5H- indolo[2, 3-a]pyrrolo-[3, 4-c]carbazole-5,7-(6H)-dione (NB-506): Induction of topoisomerase I-mediated DNA cleavage and mechanisms of cell line-selective cytotoxicity
    • Yoshinari T., Matsumoto M., Arakawa H., Okada H., Noguchi K., Suda H., Okura A., Nishimura S. (1995) Novel antitumor indolocarbazole compound 6-N-formyl-amino-12,13-dihydro-1,11-dihydroxy-13-(β-D-glucopyranosyl)-5H- indolo[2, 3-a]pyrrolo-[3, 4-c]carbazole-5,7-(6H)-dione (NB-506): induction of topoisomerase I-mediated DNA cleavage and mechanisms of cell line-selective cytotoxicity. Cancer Research, 55, 1310.
    • (1995) Cancer Research , vol.55 , pp. 1310
    • Yoshinari, T.1    Matsumoto, M.2    Arakawa, H.3    Okada, H.4    Noguchi, K.5    Suda, H.6    Okura, A.7    Nishimura, S.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.