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Volumn 6, Issue 5, 1999, Pages 277-286

Calories from carbohydrates: Energetic contribution of the carbohydrate moiety of rebeccamycin to DNA binding and the effect of its orientation on topoisomerase I inhibition

Author keywords

Carbohydrate DNA recognition; Indolocarbazole; Rebeccamycin; Stereospecificity; Topoisomerase I

Indexed keywords

ESCHERICHIA COLI;

EID: 0033133944     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(99)80073-8     Document Type: Article
Times cited : (48)

References (44)
  • 1
    • 0024394417 scopus 로고
    • Staurosporine, K-252a, and UCN-01 : Potent but nonspecific inhibitors of protein kinase
    • 1. Ruegg, U.T. & Burgess, G.M. (1989). Staurosporine, K-252a, and UCN-01 : potent but nonspecific inhibitors of protein kinase. Trends Pharmacol. Sci. 10, 218-220.
    • (1989) Trends Pharmacol. Sci. , vol.10 , pp. 218-220
    • Ruegg, U.T.1    Burgess, G.M.2
  • 2
    • 0026425587 scopus 로고
    • Antitumor activity of UCN-01, a selective inhibitor of protein kinase C, in murine and human tumor models
    • 2. Akinaga, S., Gomi, K., Morimoto, M., Tamaoki, T. & Okabe, M. (1991). Antitumor activity of UCN-01, a selective inhibitor of protein kinase C, in murine and human tumor models. Cancer Res. 51, 4888-4892.
    • (1991) Cancer Res. , vol.51 , pp. 4888-4892
    • Akinaga, S.1    Gomi, K.2    Morimoto, M.3    Tamaoki, T.4    Okabe, M.5
  • 3
    • 0030870632 scopus 로고    scopus 로고
    • Abrogation of an S-phase checkpoint and potentiation of camptothecin cytotoxicity by 7-hydroxystaurosporine (UCN-01) in human cancer cell lines, possibly influenced by p53 function
    • 3. Shao, R.G., Cao, C.X., Shimizu, T., O'Connor, P.M., Kohn, K.W. & Pommier, Y. (1997). Abrogation of an S-phase checkpoint and potentiation of camptothecin cytotoxicity by 7-hydroxystaurosporine (UCN-01) in human cancer cell lines, possibly influenced by p53 function. Cancer Res. 57, 4029-4035.
    • (1997) Cancer Res. , vol.57 , pp. 4029-4035
    • Shao, R.G.1    Cao, C.X.2    Shimizu, T.3    O'Connor, P.M.4    Kohn, K.W.5    Pommier, Y.6
  • 4
    • 0030762374 scopus 로고    scopus 로고
    • Indolocarbazoles as anti-cancer agents
    • 4. Prudhomme, M. (1997). Indolocarbazoles as anti-cancer agents. Curr. Pharm. Des. 3, 265-290.
    • (1997) Curr. Pharm. Des. , vol.3 , pp. 265-290
    • Prudhomme, M.1
  • 5
    • 0021816422 scopus 로고
    • Isolation and structure of rebeccamycin - A new antitumor antibiotic from Nocardia aerocolonigenes
    • 5. Nettleton, D.E., Doyle, T.W., Krishnan, B., Matsumoto G.K. & Clardy, J. (1985). Isolation and structure of rebeccamycin - a new antitumor antibiotic from Nocardia aerocolonigenes. Tetrahedron Lett. 26,4011-4014.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 4011-4014
    • Nettleton, D.E.1    Doyle, T.W.2    Krishnan, B.3    Matsumoto, G.K.4    Clardy, J.5
  • 6
    • 0023178261 scopus 로고
    • Production and biological activity of rebeccamycin, a novel antitumor agent
    • 6. Bush, J.A., Long, B.H., Catino, J.J., Bradner, W.T. & Tomita, K. (1987). Production and biological activity of rebeccamycin, a novel antitumor agent. J. Antibiotics 40, 668-678.
    • (1987) J. Antibiotics , vol.40 , pp. 668-678
    • Bush, J.A.1    Long, B.H.2    Catino, J.J.3    Bradner, W.T.4    Tomita, K.5
  • 7
    • 0024333037 scopus 로고
    • AT2433-A1, AT2433-A2, AT2433-B1 and AT2433-B2, novel antitumor antibiotic compounds produced by Actinomadura malliaura
    • 7. Matson, J.A., et al. & Patel, M. (1989). AT2433-A1, AT2433-A2, AT2433-B1 and AT2433-B2, novel antitumor antibiotic compounds produced by Actinomadura malliaura. J. Antibiot. 42, 1547-1555.
    • (1989) J. Antibiot. , vol.42 , pp. 1547-1555
    • Matson, J.A.1    Patel, M.2
  • 8
    • 0026678588 scopus 로고
    • Induction of mammalian DNA topoisomerase I mediated DNA cleavage by antitumor indolocarbazole derivatives
    • 8. 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, 12069-12075.
    • (1992) Biochemistry , vol.31 , pp. 12069-12075
    • Yamashita, Y.1    Fujii, N.2    Murakata, C.3    Ashizawa, T.4    Okabe, M.5    Nakano, H.6
  • 9
    • 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
    • 9. Rodrigues-Pereira E., et al. & Fabbro, D. (1996). Structure-activity relationships in a series of substituted indolocarbazoles: topoisomerase I and protein kinase C inhibition and antitumoral and antimicrobial properties. J. Med. Chem. 39, 4471-4477.
    • (1996) J. Med. Chem. , vol.39 , pp. 4471-4477
    • Rodrigues-Pereira, E.1    Fabbro, D.2
  • 10
    • 0030944043 scopus 로고    scopus 로고
    • DNA cleavage by topoisomerase I in the presence of indolocarbazole derivatives of rebeccamycin
    • 10. Bailly, C., Riou, J.F., Colson, P., Moussier, C., Rodrigues-Pereira, E. & Prudhomme, M. (1997). DNA cleavage by topoisomerase I in the presence of indolocarbazole derivatives of rebeccamycin. Biochemistry 36, 3917-3929.
    • (1997) Biochemistry , vol.36 , pp. 3917-3929
    • Bailly, C.1    Riou, J.F.2    Colson, P.3    Moussier, C.4    Rodrigues-Pereira, E.5    Prudhomme, M.6
  • 11
    • 0027461273 scopus 로고
    • Induction of topoisomerase-I-mediated DNA cleavage by a new indolocarbazole, ED-110
    • 11. Yoshinari, T., et al., & Okura, A. (1993). Induction of topoisomerase-I-mediated DNA cleavage by a new indolocarbazole, ED-110. Cancer Res. 53, 490-494.
    • (1993) Cancer Res. , vol.53 , pp. 490-494
    • Yoshinari, T.1    Okura, A.2
  • 12
    • 0028931509 scopus 로고
    • Novel antitumor 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): Induction of topoisomerase-I-mediated DNA cleavage and mechanisms of cell line-selective cytotoxicity
    • 12. Yoshinari, T., et al., & Nishimura, S. (1995). Novel antitumor 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): induction of topoisomerase-I-mediated DNA cleavage and mechanisms of cell line-selective cytotoxicity. Cancer Res. 55, 1310-1315.
    • (1995) Cancer Res. , vol.55 , pp. 1310-1315
    • Yoshinari, T.1    Nishimura, S.2
  • 13
    • 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
    • 13. Arakawa, H., et al., & 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 Res. 55, 1316-1320.
    • (1995) Cancer Res. , vol.55 , pp. 1316-1320
    • Arakawa, H.1    Nishimura, S.2
  • 14
    • 0003267271 scopus 로고    scopus 로고
    • Phase I and pharmacology study of 5-day infusion of NB-506
    • 14. Ohe, Y., et al., & Sasaki, Y. (1997). Phase I and pharmacology study of 5-day infusion of NB-506. Proc. ACSO 16, 199a.
    • (1997) Proc. ACSO , vol.16
    • Ohe, Y.1    Sasaki, Y.2
  • 15
    • 0031965431 scopus 로고    scopus 로고
    • New chemotherapeutic agents for the treatment of non-small cell lung cancer
    • 15. Saijo, N. (1998). New chemotherapeutic agents for the treatment of non-small cell lung cancer. Chest 113, 1 7S-25S.
    • (1998) Chest , vol.113
    • Saijo, N.1
  • 16
    • 0031938920 scopus 로고    scopus 로고
    • Recognition of specific sequences in DNA by a topoisomerase I inhibitor derived from the antitumor drug rebeccamycin
    • 16. Bailly, C., Colson, P., Moussier, C., Rodrigues-Pereira, E., Prudhomme, M. & Waring, M.J. (1998). Recognition of specific sequences in DNA by a topoisomerase I inhibitor derived from the antitumor drug rebeccamycin. Mol. Pharmacol. 53, 77-87.
    • (1998) Mol. Pharmacol. , vol.53 , pp. 77-87
    • Bailly, C.1    Colson, P.2    Moussier, C.3    Rodrigues-Pereira, E.4    Prudhomme, M.5    Waring, M.J.6
  • 17
    • 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
    • 17. 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. Quart. Rev. Biophys. 11, 103-178.
    • (1978) Quart. Rev. Biophys. , vol.11 , pp. 103-178
    • Record, M.T.1    Anderson, C.F.2    Lohman, T.M.3
  • 18
    • 0021689084 scopus 로고
    • Polyelectrolyte effects on site-binding equilibria with application to the intercalation of drugs into DNA
    • 18. Friedman, R.A. & Manning, G.S. (1984). Polyelectrolyte effects on site-binding equilibria with application to the intercalation of drugs into DNA. Biopolymers 23, 2671-2714.
    • (1984) Biopolymers , vol.23 , pp. 2671-2714
    • Friedman, R.A.1    Manning, G.S.2
  • 19
    • 0027295656 scopus 로고
    • Dissection of the free energy of anthracycline antibiotic binding to DNA: Electrostatic contributions
    • 19. 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. J. Am. Chem. Soc. 115, 5360-5364.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 5360-5364
    • Chaires, J.B.1    Priebe, W.2    Graves, D.E.3    Burke, T.G.4
  • 20
    • 0002304026 scopus 로고
    • Some thermodynamic principles of nonspecific and site-specific protein-DNA interactions
    • (Revzin, A., ed.), CRC Press, Boca Raton, FL
    • 20. Record, M.T., Jr. & Spolar. R. (1990). Some thermodynamic principles of nonspecific and site-specific protein-DNA interactions. The Biology of Nonspecific DNA-Protein Interactions. (Revzin, A., ed.). pp. 33-69, CRC Press, Boca Raton, FL.
    • (1990) The Biology of Nonspecific DNA-protein Interactions , pp. 33-69
    • Record M.T., Jr.1    Spolar, R.2
  • 21
    • 0026323912 scopus 로고
    • Analysis of equilibrium and kinetic measurements to determine thermodynamic origins of stability and specificity and mechanism of formation of site-specific complexes between proteins and helical DNA
    • 21. Record, M.T., Jr., Ha, J.H. & Fisher, M.A. (1991). Analysis of equilibrium and kinetic measurements to determine thermodynamic origins of stability and specificity and mechanism of formation of site-specific complexes between proteins and helical DNA. Methods Enzymol. 208, 291-343.
    • (1991) Methods Enzymol. , vol.208 , pp. 291-343
    • Record M.T., Jr.1    Ha, J.H.2    Fisher, M.A.3
  • 22
    • 0014202608 scopus 로고
    • A fluorescent complex between ethidium bromide and nucleic acids
    • 22. Le Pecq, J.B. & Paoletti, C. (1967). A fluorescent complex between ethidium bromide and nucleic acids. J. Mol. Biol. 27, 87-106.
    • (1967) J. Mol. Biol. , vol.27 , pp. 87-106
    • Le Pecq, J.B.1    Paoletti, C.2
  • 23
    • 0029026601 scopus 로고
    • Criteria for the mode of binding of DNA binding agents
    • 23. Suh, D. & Chaires, J.B. (1995). Criteria for the mode of binding of DNA binding agents. Bioorg. Med. Chem. 3, 723-728
    • (1995) Bioorg. Med. Chem. , vol.3 , pp. 723-728
    • Suh, D.1    Chaires, J.B.2
  • 25
    • 15144351325 scopus 로고    scopus 로고
    • Syntheses and biological evaluation of indolocarbazoles, analogs of rebeccamycin, modified at the imide heterocycle
    • 25. Moreau, P., et al., & Aubertin, A.M. (1998). Syntheses and biological evaluation of indolocarbazoles, analogs of rebeccamycin, modified at the imide heterocycle. J. Med. Chem. 41, 1631-1640.
    • (1998) J. Med. Chem. , vol.41 , pp. 1631-1640
    • Moreau, P.1    Aubertin, A.M.2
  • 26
    • 0031308164 scopus 로고    scopus 로고
    • Diethylpyrocarbonate and osmium tetroxide as probes for drug-induced changes in DNA conformation in vitro
    • (Fox, K.R., ed), Humana Press, Totowa, NJ
    • 26. Bailly, C. & Waring, M.J. (1997). Diethylpyrocarbonate and osmium tetroxide as probes for drug-induced changes in DNA conformation in vitro. In Drug-DNA Interactions: Methods, Case Studies, and Protocols. Methods in Molecular Biology, volume 90. (Fox, K.R., ed). pp. 51-79, Humana Press, Totowa, NJ.
    • (1997) Drug-DNA Interactions: Methods, Case Studies, and Protocols. Methods in Molecular Biology , vol.90 , pp. 51-79
    • Bailly, C.1    Waring, M.J.2
  • 28
    • 0030465221 scopus 로고    scopus 로고
    • Dissecting the free energy of drug binding to DNA
    • 28. Chaires, J.B. (1996). Dissecting the free energy of drug binding to DNA. Anti-Cancer Drug Des. 11, 569-580.
    • (1996) Anti-cancer Drug Des. , vol.11 , pp. 569-580
    • Chaires, J.B.1
  • 29
    • 0029141654 scopus 로고
    • Strategies for the design of minor groove binders: A re-evaluation based on the emergence of site-selective carbohydrate binders
    • 29. Kahne, D. (1995). Strategies for the design of minor groove binders: a re-evaluation based on the emergence of site-selective carbohydrate binders. Chem. Biol. 2, 7-12.
    • (1995) Chem. Biol. , vol.2 , pp. 7-12
    • Kahne, D.1
  • 30
    • 0029861709 scopus 로고    scopus 로고
    • Intervention of carbohydrate recognition by proteins and nucleic acids
    • 30. Sears, P. & Wong, C.H. (1996). Intervention of carbohydrate recognition by proteins and nucleic acids. Proc. Natl Acad. Sci. USA 93, 12086-12093.
    • (1996) Proc. Natl Acad. Sci. USA , vol.93 , pp. 12086-12093
    • Sears, P.1    Wong, C.H.2
  • 32
    • 0004971606 scopus 로고
    • Interaction of calicheamicin with duplex DNA: Role of the oligosaccharide domain and identification of multiple binding modes
    • 32. Paloma, L.G., Smith, J.A., Chazin, W.J. & Nicolaou, K.C. (1994). Interaction of calicheamicin with duplex DNA: role of the oligosaccharide domain and identification of multiple binding modes. J. Am. Chem. Soc. 116, 3697-3708.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 3697-3708
    • Paloma, L.G.1    Smith, J.A.2    Chazin, W.J.3    Nicolaou, K.C.4
  • 34
    • 0029927534 scopus 로고    scopus 로고
    • The role of the aminosugar and helix binding in the thiol-induced activation of calicheamicin for DNA cleavage
    • 34. Chatterjee, M., Smith, P.J. & Townsend, C.A. (1996). The role of the aminosugar and helix binding in the thiol-induced activation of calicheamicin for DNA cleavage. J. Am. Chem. Soc. 118, 1938-1948.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1938-1948
    • Chatterjee, M.1    Smith, P.J.2    Townsend, C.A.3
  • 37
    • 0030034725 scopus 로고    scopus 로고
    • Sequence-selective carbohydrate-DNA interaction: Dimeric and monomeric forms of calicheamicin oligosaccharide interfere with transcription factor function
    • 37. Liu, C., et al., & Vogt, P.K. (1996). Sequence-selective carbohydrate-DNA interaction: dimeric and monomeric forms of calicheamicin oligosaccharide interfere with transcription factor function. Proc. Natl Acad. Sci. USA 93, 940-944.
    • (1996) Proc. Natl Acad. Sci. USA , vol.93 , pp. 940-944
    • Liu, C.1    Vogt, P.K.2
  • 38
    • 0028136464 scopus 로고
    • Specific inhibition of formation of transcription complexes by a calicheamicin oligosaccharide: A paradigm for the development of transcriptional antagonists. Proc. Natl
    • 38. Ho, S.N., Boyer, S.H., Schreiber, S.L., Danishefsky, S.J. & Crabtree, G.R. (1994). Specific inhibition of formation of transcription complexes by a calicheamicin oligosaccharide: a paradigm for the development of transcriptional antagonists. Proc. Natl Acad. Sci. USA 91, 9203-9207.
    • (1994) Acad. Sci. USA , vol.91 , pp. 9203-9207
    • Ho, S.N.1    Boyer, S.H.2    Schreiber, S.L.3    Danishefsky, S.J.4    Crabtree, G.R.5
  • 39
    • 0030925110 scopus 로고    scopus 로고
    • A comparison of DNA cleavage by neocarzinostatin chromophore and its aglycone: Evaluating the role of the carbohydrate residue
    • 39. Myers, A.G., Kort, M.E. & Hammond, M. (1997). A comparison of DNA cleavage by neocarzinostatin chromophore and its aglycone: evaluating the role of the carbohydrate residue. J. Am. Chem. Soc. 119, 2965-2972.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 2965-2972
    • Myers, A.G.1    Kort, M.E.2    Hammond, M.3
  • 40
    • 0030887815 scopus 로고    scopus 로고
    • Saccharide-RNA recognition in an aminoglycoside antibiotic-RNA aptamer complex
    • 40. Jiang, L., Suri, A.K., Fiala, R. & Patel, D.J. (1997). Saccharide-RNA recognition in an aminoglycoside antibiotic-RNA aptamer complex. Chem. Biol. 4, 35-50.
    • (1997) Chem. Biol. , vol.4 , pp. 35-50
    • Jiang, L.1    Suri, A.K.2    Fiala, R.3    Patel, D.J.4
  • 41
    • 0023151436 scopus 로고
    • Interactions between an anthracycline antibiotic and DNA: Molecular structure of daunomycin complexed to d(CpGpTpApCpG) at 1.2 Å resolution
    • 41. Wang, A.H.J., Ughetto, G., Quigley, G.J. & Rich, A. (1987). Interactions between an anthracycline antibiotic and DNA: molecular structure of daunomycin complexed to d(CpGpTpApCpG) at 1.2 Å resolution. Biochemistry 26, 1152-1163.
    • (1987) Biochemistry , vol.26 , pp. 1152-1163
    • Wang, A.H.J.1    Ughetto, G.2    Quigley, G.J.3    Rich, A.4
  • 42
    • 0025355676 scopus 로고
    • Structural comparison of anticancer drug-DNA complexes: Adriamycin and daunomycin
    • 42. Frederick, C. A., et al., & Wang, A. H.-J. (1990). Structural comparison of anticancer drug-DNA complexes: adriamycin and daunomycin. Biochemistry 29, 2538-2549.
    • (1990) Biochemistry , vol.29 , pp. 2538-2549
    • Frederick, C.A.1    Wang, A.H.-J.2
  • 43
    • 0025345159 scopus 로고
    • Biophysical chemistry of the daunomycin-DNA interaction
    • 43. Chaires, J.B. (1990). Biophysical chemistry of the daunomycin-DNA interaction. Biophys. Chem. 35, 191-202.
    • (1990) Biophys. Chem. , vol.35 , pp. 191-202
    • Chaires, J.B.1
  • 44
    • 9844260513 scopus 로고    scopus 로고
    • Syntheses and biological activity (topoisomerases inhibition, antitumoral and antimicrobial properties) of rebeccamycin analogs bearing modified sugar moieties and substituted on the imide nitrogen with a methyl group
    • 44. Anizon, F., et al., & Meyer, T. (1997). Syntheses and biological activity (topoisomerases inhibition, antitumoral and antimicrobial properties) of rebeccamycin analogs bearing modified sugar moieties and substituted on the imide nitrogen with a methyl group. J. Med. Chem. 40, 3456-3465.
    • (1997) J. Med. Chem. , vol.40 , pp. 3456-3465
    • Anizon, F.1    Meyer, T.2


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