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Vibriobactin Antibodies: A Vaccine Strategy

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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Med. Chem. 2009, 52, 12, 3801-3813
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    Vibriobactin Antibodies: A Vaccine Strategy
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    Department of Medicinal Chemistry and the Hybridoma Core Laboratory, Interdisciplinary Center for Biotechnology Research, University of Florida, Gainesville, Florida 32610-0485
    * To whom correspondence should be addressed. Phone: (352) 273-7725. Fax: (352) 392-8406. E-mail: [email protected]
    †Department of Medicinal Chemistry.
    ‡Hybridoma Core Laboratory, Interdisciplinary Center for Biotechnology Research.
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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2009, 52, 12, 3801–3813
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jm900119q
    Published June 3, 2009
    Copyright © 2009 American Chemical Society
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    Abstract

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    A new target strategy in the development of bacterial vaccines, the induction of antibodies to microbial outer membrane ferrisiderophore complexes, is explored. A vibriobactin (VIB) analogue, with a thiol tether, 1-(2,3-dihydroxybenzoyl)-5,9-bis[[(4S,5R)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-5-methyl-4-oxazolyl]carbonyl]-14-(3-mercaptopropanoyl)-1,5,9,14-tetraazatetradecane, was synthesized and linked to ovalbumin (OVA) and bovine serum albumin (BSA). The antigenicity of the VIB microbial iron chelator conjugates and their iron complexes was evaluated. When mice were immunized with the resulting OVA−VIB conjugate, a selective and unequivocal antigenic response to the VIB hapten was observed; IgG monoclonal antibodies specific to the vibriobactin fragment of the BSA and OVA conjugates were isolated. The results are consistent with the idea that the isolated adducts of siderophores covalently linked to their bacterial outer membrane receptors represent a credible target for vaccine development.

    Copyright © 2009 American Chemical Society

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    Elemental analytical data for synthesized compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cited By

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    This article is cited by 26 publications.

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    Journal of Medicinal Chemistry

    Cite this: J. Med. Chem. 2009, 52, 12, 3801–3813
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jm900119q
    Published June 3, 2009
    Copyright © 2009 American Chemical Society
    Request reuse permissions

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