10
Views
11
CrossRef citations to date
0
Altmetric
Original Articles

Quantum Chemical and Molecular Mechanics Studies on the Binding of Stereoisomers of the Oligopeptide Antibiotics Amidinomycin and Noformycin to the Minor Groove of B-DNA

, , , , &
Pages 709-726 | Received 13 Jun 1992, Published online: 21 May 2012

References and Footnotes

  • Pullman , B. and Jortner , J. , eds. 1990 . “Molecular Basis of Specificity in Nucleic Acid-Drug Interaction” London : Kluwer Academic Publishers .
  • Dervan , P. B. 1986 . Science , 232 : 464
  • Neilsen , P. 1990 . Bioconjugate Chem. , 1 : 1
  • Bailly , C. and Henichart , J.-P. 1991 . Bioconjugate Chem. , 2 : 379
  • Pullman , B. 1989 . Adv. Drug. Res. , 18 : 1
  • Zimmer , C. and Wahnert , U. 1986 . Prog. Biophys. Mol. Biol. , 47 : 31
  • Reynolds , V. L. , Molineux , L. J. , Kaplan , D. , Swenson , D. H. and Hurley , L. H. 1985 . Biochemistry , 24 : 6628
  • Hurley , L. H. , Reck , T. , Thurston , D. E. , Langley , D. R. , Holden , K. G. , Hertzberg , R. P. , Hoover , J. R.E. , Gallagher , G. , Faucette , L. F. , Mong , S. M. and Johnson , R. K. 1988 . Chem. Res. Toxicol. , 1 : 258
  • Stubbe , J. and Kozarich , J. W. 1987 . Chem. Revs. , 87 : 1107
  • Rao , K. E. and Lown , J. W. 1990 . Chem. Res. Toxicol. , 3 : 262
  • Takaishi , T. , Sugawara , Y. and Suzuki , M. 1972 . Tetrahedron Lett. , 1873 (a)(b) Kikuchi, M., Kumagai, K., Ishida, N., Ito, Y., Yamaguchi, T., Furumai, T. and Okuda, T.J., Antibiot. Ser. A18, 243 (1965). (c) Lee, M. and Lown, J.W., J. Org. Chem. 52, 5717 (1987). (d) Lee, M., Shea, R.G., Hartley, J.A., Lown, J.W., Kissinger, K., Dabrowiak, J.C., Vesnaver, G., Breslauer, K.J. and Pon, R.T., J. Mol. Recogn. 1, 6 (1989)
  • Probst , G. W. , Hoehn , M. M. and Woods , B. L. 1965 . Antimicrob, Agents Chemother. , 789 : 1961 (a) (b) Lee, M., Coulter, D.M. and Lown, J.W., J. Org. Chem. 53, 1855 (1988). (c) Lee, M., Shea, R.G., Hartley, J.A., Kissinger, K., Pon, R.T., Vesnaver, G., Breslauer, K.J., Dabrowiak, J.C. and Lown, J.W., J. Am. Chem. Soc. 111, 345 (1989)
  • Arcamone , F. , Orezzi , P. G. , Barbieri , W. , Nicolella , V. and Penco , S. 1967 . Gazi. Chim. Ital , 97 : 1097 (a) (b) Hahn, F.E., In Antibiotics III. Mechanism of Action of Antimucribial and Antitumor Agents, Corcoran, J.W., Hahn, F.E. (eds.). Springer-Verlag, New York, 1975, p. 75
  • Julia , M. and Préau-Joseph , N. 1967 . Bull. Soc. Chim. Fr. , 4348
  • Nakamura , S. , Karasawa , K. , Tanaka , N. , Yonehara , H. and Umezawa , H. 1960 . J. Antibiot. Ser. A , 13 : 362 (a) (b) Nakamura, S., Karasawa, K., Yonehara, H., Tanaka, N. and Umezawa, H., J., Antibiot. Ser. A 14, 103 (1961). (c) Nakamura, S., Chem. Pharm. Bull. 9, 641 (1961). (d) Allan, R.D., Johnston, G.A.R. and Twitchin, B., Aust. J. Chem. 32, 2517 (1979). (e) Kaneda, M., Nakamura, S. and Iitaka, Y., J. Antibiot. Ser. A. 33, 778 (1980)
  • Diana , G. D. 1973 . J. Med. Chem. , 16 : 857
  • Hahn , F. E. 1975 . In Antibiotics III. Mechanism of Action of Antimucribial and Antitumor Agents Edited by: Corcoran , J. W. and Hahn , F. E. 79 New York : Springer-Verlag .
  • Kissinger , K. , Krowicki , K. , Dabrowiak , J. C. and Lown , J. W. 1987 . Biochemistry , 26 : 5590
  • Rao , K. E. , Krowicki , K. , Burckhardt , G. , Zimmer , C. and Lown , J. W. 1991 . Chem. Res. Toxicol. , 4 : 241
  • Rao , K. E. , Shea , R. G. , Yadagiri , B. and Lown , J. W. 1990 . Anti-Cancer Drug Design , 5 : 3
  • Lown , J. W. 1988 . Anti-Cancer Drug Design , 3 : 35 (a) (b) Lown, J.W., Krowicki, K., Balzarini, J., Newman, R.A. and De Clercq, E., 32, 2368 (1989). (c) Wang, W. and Lown, J.W., J. Med. Chem. 35, 2890 (1992)
  • Lown , J. W. 1990 . Molecular Basis of Specificity in Nucleic Acid-Drug Interaction 103 London : Kluwer Academic Publishers . (a) (b) Lown, J.W. Antiviral Res. 17, 179 (1992)
  • Beerman , T. A. , Sigmund , R. D. , Gawron , L. S. , Woynarowski , J. M. , Rao , K. E. and Lown , J. W. 1991 . Biochem. Biophys. Acta , 1090 : 52
  • Rao , K. E. , Zimmermann , J. and Lown , J. W. 1991 . J. Org. Chem. , 56 : 786
  • Gago , F. , Reynolds , G. A. and Richards , W. G. 1989 . Mol. Pharmacol. , 35 : 236
  • Mazurek , P. , Feng , W. , Shukla , K. , Sapse , A.-M. and Lown , J. W. 1991 . J. Biomol. Struct. Dyn. , 9 : 299
  • Lavery , R. and Pullman , B. 1985 . J. Biomol. Struct. Dyn. , 2 : 101 (a) (b) Lavery, R., Pullman, A. and Pullman, B., Theoretica Chim. Acta 62, 93 (1982). (c) Lavery, R., Zakrowski, K. and Pullman, A., Comput. Chem. 5, 363 (1984). (d) Pullman, A. and Pullman, B., Quart. Rev. Biophys. 14, 289 (1981). (e) Zakrewska, K., Lavery, R. and Pullman, B., J. Biomol. Struct. Dyn. 4, 833 (1987). (f) Pullman, B., Adv. Drug Res. 18, 1 (1989)
  • Frisch , M. J. , Brinkley , J. S. , Schlegel , H. B. , Raghavachari , K. , Melius , C. F. , Martin , R. L. , Stewart , J. J.P. , Bobrowicz , F. W. , Rohlfing , C. M. , Kahn , L. R. , Defrees , D. J. , Seeger , R. , Whiteside , R. A. , Fox , D. J. , Fleuder , E. M. and Pople , J. A. 1986 . “Gaussian 88” Pittsburgh , PA : Carnegie-Mellon Quantum Publishing Unit .
  • Holbrook , S. R. , Dickerson , R. E. and Kein , H. 1985 . Acta Crystallogr. Sec. B , 41 : 255
  • Rao , K. E. , Shea , R. G. , Bathini , Y. and Lown , J. W. 1990 . Anti-Cancer Drug Design , 5 : 3
  • Kumar , S. , Jaseja , M. , Zimmermann , J. , Bathini , Y. , Pon , R. T. , Sapse , A.-M. and Lown , J. W. 1990 . J. Biomol. Struct. Dyn. , 8 : 99
  • Youngquist , R. C. and Dervan , P. B. 1985 . Proc. Natl. Acad. Sci. USA , 82 : 2565
  • Stevens , M. 1989 . New Scientist , 11 : 37
  • Rao , K. E. , Padmanabhan , S. and Lown , J. W. 1992 . Actual. Chim. Therapeut , in press

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.