Structure-activity relationship studies on UK-2A, a novel antifungal antibiotic from Streptomyces sp. 517-02. Part 5: Roles of the 9-membered dilactone-ring moiety in respiratory inhibition

Yoshinosuke Usuki; Noriko Adachi; Ken-ichi Fujita; Akio Ichimura; Hideo Iio; Makoto Taniguchi

doi:10.1016/j.bmcl.2006.03.023

Structure-activity relationship studies on UK-2A, a novel antifungal antibiotic from Streptomyces sp. 517-02. Part 5: Roles of the 9-membered dilactone-ring moiety in respiratory inhibition

Bioorg Med Chem Lett. 2006 Jun 15;16(12):3319-22. doi: 10.1016/j.bmcl.2006.03.023. Epub 2006 Mar 27.

Authors

Yoshinosuke Usuki¹, Noriko Adachi, Ken-ichi Fujita, Akio Ichimura, Hideo Iio, Makoto Taniguchi

Affiliation

¹ Department of Material Science, Graduate School of Science, Osaka City University, 3-3-138 Sugimoto, Sumiyoshi, Osaka 558-8585, Japan. usuki@sci.osaka-cu.ac.jp

PMID: 16564168
DOI: 10.1016/j.bmcl.2006.03.023

Abstract

Several open-chained analogues of UK-2A, a novel antifungal antibiotic isolated from Streptomyces sp. 517-02, were prepared for structure-activity studies. The in vitro antifungal activities of these compounds against Rhodotorula mucilaginosa IFO 0001 and the inhibition of uncoupler-stimulated respiration in bovine heart submitochondrial particles (SMP) were evaluated. Oxidative potentials were measured by cyclic voltammetry. An analogue prepared from dihexyl L-glutamate showed comparable inhibitory activity as UK-2A.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antifungal Agents / chemical synthesis*
Antifungal Agents / chemistry
Antifungal Agents / pharmacology*
Cattle
Heart / drug effects*
Lactones / chemical synthesis
Lactones / chemistry*
Lactones / pharmacology
Molecular Structure
Pyridines / chemical synthesis
Pyridines / chemistry
Pyridines / pharmacology
Streptomyces / chemistry*
Streptomyces / classification
Structure-Activity Relationship

Substances

Antifungal Agents
Lactones
Pyridines
UK 2A