Document Type


Publication Date

December 2007


This article has been peer reviewed. It is the authors' final version prior to publication in Bioorganic & Medicinal Chemistry Letters 17(23):6558-6562, December 2007. The published version is available at; copyright © 2007 Elsevier, Ltd.


The need for self-protecting polymer or alloy implants resistant to a broad spectrum of bacterial challenges led us to investigate covalent bonding of minocycline (MIN), a tetracycline derivative, to polystyrene beads and to titanium alloy foils by oligoethylene glycol spacers. 9-Hydrazino-acetyl-amido-MIN, and simpler glycylcycline derivatives, retained minimum inhibitory concentration (MIC) against Staphylococcus aureus comparable to MIN. However, PEG-glycyl-amido-MIN showed very low activity. Hence, we coupled 9-hydrazino-acetyl-amido-MIN to the aldehyde termini of oligoethylene glycol spacers bonded to polystyrene and titanium alloy surfaces to form acid-releasable hydrazone linkages. 9-Hydrazino-acetyl-amido-MIN was released from the monolayers more rapidly at pH 5.0 than at pH 7.4.



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