The macrocycle of leinamycin imparts hydrolytic stability to the thiol-sensing 1,2-dithiolan-3-one 1-oxide unit of the natural product

Santhosh Sivaramakrishnan, Leonid Breydo, Daekyu Sun, Kent S. Gates

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Reaction of cellular thiols with the 1,2-dithiolan-3-one 1-oxide moiety of leinamycin triggers the generation of DNA-damaging reactive intermediates. Studies with small, synthetic analogues of leinamycin reveal that the macrocyclic portion of the natural product imparts remarkable hydrolytic stability to the 1,2-dithiolan-3-one 1-oxide heterocycle without substantially compromising its thiol-sensing property.

Original languageEnglish (US)
Pages (from-to)3791-3794
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number11
DOIs
StatePublished - Jun 1 2012

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Biological Products
Sulfhydryl Compounds
Oxides
DNA
leinamycin

Keywords

  • DNA cleavage
  • DNA damage

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

Cite this

The macrocycle of leinamycin imparts hydrolytic stability to the thiol-sensing 1,2-dithiolan-3-one 1-oxide unit of the natural product. / Sivaramakrishnan, Santhosh; Breydo, Leonid; Sun, Daekyu; Gates, Kent S.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 22, No. 11, 01.06.2012, p. 3791-3794.

Research output: Contribution to journalArticle

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