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Membrane-active antimicrobial poly(amino-modified alkyl) β-cyclodextrins synthesized via click reactions

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Abstract

The emergence of drug-resistant bacteria has led to the high demand for new antibiotics. In this report, we investigated membrane-active antimicrobial β-cyclodextrins. These contain seven amino-modified alkyl groups on a molecule, which act as functional moieties to permeabilize bacterial cell membranes. The polyfunctionalization of cyclodextrins was achieved through a click reaction assisted by microwave irradiation. A survey using derivatives with systematically varied functionalities clarified the unique correlation of the antimicrobial activity of these compounds with their molecular structure and hydrophobicity/hydrophilicity balances. The optimum hydrophobicity for the compounds being membrane-active was specific to bacterial strains and animal cells; this led to specific compounds having selective toxicity against bacteria including multidrug-resistant pathogens. The results demonstrate that cyclodextrin is a versatile molecular scaffold for rationally designed structures and can be used for the development of new antibiotics.

Graphical abstract: Membrane-active antimicrobial poly(amino-modified alkyl) β-cyclodextrins synthesized via click reactions

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Publication details

The article was received on 21 Nov 2017, accepted on 17 Jan 2018 and first published on 08 Feb 2018


Article type: Research Article
DOI: 10.1039/C7MD00592J
Citation: Med. Chem. Commun., 2018, Advance Article
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    Membrane-active antimicrobial poly(amino-modified alkyl) β-cyclodextrins synthesized via click reactions

    H. Yamamura, M. Nonaka, S. Okuno, R. Mitsuhashi, H. Kato, T. Katsu, K. Masuda, K. Tanimoto, H. Tomita and A. Miyagawa, Med. Chem. Commun., 2018, Advance Article , DOI: 10.1039/C7MD00592J

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