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Synthesis and antibacterial activity of doxycycline neoglycosides.

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-?-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.

SUBMITTER: Zhang J

PROVIDER: S-EPMC3814126 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature

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Synthesis and antibacterial activity of doxycycline neoglycosides.

Zhang Jianjun J Ponomareva Larissa V LV Marchillo Karen K Zhou Maoquan M Andes David R DR Thorson Jon S JS

Journal of natural products 20130829 9

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 ...[more]

PMID: 23987662

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