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  • Title: Inhibitory effect of beta-cyclodextrin on ampicillin polymerization in aqueous solution.
    Author: Aki H, Yamamoto K, Sawai N, Yamamoto M.
    Journal: Drug Des Deliv; 1990 Dec; 7(1):59-63. PubMed ID: 2096835.
    Abstract:
    Ampicillin polymerizes in aqueous solution to produce antigenic polymers; the polymers were separated by anion-exchange chromatography and shown to consist of a dimer, trimer, tetramer and pentamer of ampicillin by the masses found in fast atom bombardment mass spectroscopy. The presence of an intact beta-lactam ring in each of the polymers was revealed by the characteristic positive Cotton effect near 230 nm in their circular dichroism spectra. beta-Cyclodextrin was found to inhibit this polymerization by complex formation involving equimolar quantities of the constituents. Formation of this complex was complete in 10% aqueous solution within 6 hr at 24 degrees C. The positive Cotton effect arising from the beta-lactam ring decreased as the degree of polymerization increased, but was unchanged by the complex formation with beta-cyclodextrin.
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