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Organische Chemie I - Prof. Dr. Rainer Schobert

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Trojan Antibiotics: Penicillin−Siderophor Conjugates

Resistance of microbial pathogens against beta−lactam antibiotics is a haunting problem for the clinician. Gram−negative bacteria are especially hard to tackle due to their outer membrane permeability barrier which can be overcome, though, by transporter−mediated active internalisation of specific compounds such as siderophores.
These are microbial secondary metabolites, excreted to sequester extracellular ferric ions. Specific outer membrane receptors then recognise the siderophore−iron complex and initiate its transport into the cell. Many natural siderophores are tris−bidentate ligands with catechol, salicylate or hydroxamate motifs.
This active import of ferrisiderophores also opens a flank in the microbial defence strategy. There are many examples of natural conjugates of siderophores with antibiotic effectors mainly produced by Streptomyces (sideromycins).
Following this "trojan horse" strategy we develop covalent beta−lactam−siderophore conjugates of various types to sneak past the microbial defence barrier.

Tetrahedron, 62, 2006, 7799
Tetrahedron, 64, 2008, 1711

Verantwortlich für die Redaktion: André Wetzel

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