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

ABSTRACT: The emergence of drug-resistant bacteria has led to the high demand for new antibiotics. In this report, we investigated membrane-active antimicrobial ?-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.

SUBMITTER: Yamamura H 

PROVIDER: S-EPMC6072522 | biostudies-other | 2018 Mar

REPOSITORIES: biostudies-other

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Membrane-active antimicrobial poly(amino-modified alkyl) β-cyclodextrins synthesized <i>via</i> click reactions.

Yamamura Hatsuo H   Nonaka Miho M   Okuno Shingo S   Mitsuhashi Ryogo R   Kato Hisato H   Katsu Takashi T   Masuda Kazufumi K   Tanimoto Koichi K   Tomita Haruyoshi H   Miyagawa Atsushi A  

MedChemComm 20180208 3

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 clarifie  ...[more]