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Streptonigrin and lavendamycin partial structures - probes for the minimum, potent pharmacophore of streptonigrin, lavendamycin, and synthetic quinoline-5,8-diones

Academic Article
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Overview

authors

  • Boger, Dale
  • Yasuda, M.
  • Mitscher, L. A.
  • Drake, S. D.
  • Kitos, P. A.
  • Thompson, S. C.

publication date

  • October 1987

journal

  • Journal of Medicinal Chemistry  Journal

abstract

  • The preparation and evaluation of 7-amino-5,8-dioxo-2-(2'-pyridyl)quinoline-6'-carboxylic acid (5a) and 7-amino-2-(2'-aminophenyl)-5,8-dioxoquinoline-5'-carboxylic acid (6a) constituting potential minimum, potent pharmacophores of streptonigrin (1a) and lavendamycin (2a), two structurally related naturally occurring antitumor antibiotics, are detailed. In contrast to observations associated with streptonigrin and lavendamycin in which the C-ring C-6' carboxylic acid potentiates the antitumor, antimicrobial, and cytotoxic properties of the naturally occurring, substituted 7-aminoquinoline-5,8-dione AB ring systems, the C-6'/C-5' carboxylic acid of 5a/6a diminishes the observed antimicrobial and cytotoxic properties of the 2-(2'-pyridyl)- and 2-(2'-aminophenyl)-7-aminoquinoline-5,8-diones. A direct comparison of the antimicrobial and cytotoxic properties of a complete set of streptonigrin and lavendamycin partial structures is detailed in efforts to define the role peripheral substituents play in potentiating the biological properties of the naturally occurring and synthetic agents bearing the 7-aminoquinoline-5,8-dione AB ring system and in efforts to define the minimum, potent pharmacophore of the naturally occurring antitumor antibiotics. The relationship of these observations to a chemical mechanism of cellular toxicity is discussed.

subject areas

  • Animals
  • Antibiotics, Antineoplastic
  • Chemistry, Physical
  • Leukemia L1210
  • Melanoma
  • Mice
  • Microbial Sensitivity Tests
  • Physicochemical Phenomena
  • Quinolines
  • Streptonigrin
  • Structure-Activity Relationship
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Identity

International Standard Serial Number (ISSN)

  • 0022-2623

Digital Object Identifier (DOI)

  • 10.1021/jm00393a040

PubMed ID

  • 3656364
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Additional Document Info

start page

  • 1918

end page

  • 1928

volume

  • 30

issue

  • 10

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