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A convenient synthetic pathway for multivalent assembly of aminoglycoside antibiotics starting from amikacin
Hidehiko Tanaka1, Yoshihiro Nishida, Yousuke Furuta
1Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan.
Bioorganic & Medicinal Chemistry Letters
|June 18, 2002
Abstract:
Vinylpolymers carrying a kanamycin cluster at the side chain were prepared via regioselective N-acylation of amikacin with N-succinimidyl p-vinylbenzoate, followed by radical homo- and co-polymerization with acrylamide. Two independent biological assays disclosed that the polyvalent kanamycin models showed neither antibacterial activity nor inhibitory activity against rRNA-based protein synthesis, suggesting that the multivalency-binding approach is not valid for integrating the potential of aminoglyoside anitibiotics.