Synthesis and antibacterial activity of doxycycline neoglycosides

Jianjun Zhang, Larissa V. Ponomareva, Karen Marchillo, Maoquan Zhou, David R. Andes, Jon S. Thorson

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

A set of 37 doxycycline neoglycosides were prepared, mediated via a C-9 alkoxyamino-glycyl-based spacer reminiscent of that of tigecycline. Subsequent in vitro antibacterial assays against representative drug-resistant Gram negative and Gram positive strains revealed a sugar-dependent activity profile and one doxycycline neoglycoside, the 2′-amino-α-d-glucoside conjugate, to rival that of the parent pharmacophore. In contrast, the representative tetracycline-susceptible strain E. coli 25922 was found to be relatively responsive to a range of doxycycline neoglycosides. This study also extends the use of aminosugars in the context of neoglycosylation via a simple two-step strategy anticipated to be broadly applicable for neoglycorandomization.

Original languageEnglish
Pages (from-to)1627-1636
Number of pages10
JournalJournal of Natural Products
Volume76
Issue number9
DOIs
StatePublished - Sep 27 2013

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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