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Rule of Hydrophobicity/Hydrophilicity Balance in Membrane‐Disrupting Antimicrobial Activity of Polyalkylamino Cyclodextrins Synthesized via Click Chemistry
Author(s) -
Yamamura Hatsuo,
Miyagawa Atsushi,
Sugiyama Hiroki,
Murata Kensuke,
Mabuti Takahiro,
Mitsuhashi Ryogo,
Hagiwara Tatsuya,
aka Miho,
Tanimoto Koichi,
Tomita Haruyoshi
Publication year - 2016
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201500017
Subject(s) - antimicrobial , chemistry , click chemistry , bacteria , membrane , cyclodextrin , combinatorial chemistry , molecule , staphylococcus aureus , antibiotics , biophysics , biochemistry , organic chemistry , biology , genetics
Emergence of drug‐resistant bacterial pathogens and the concurrent demand for new antibiotics has led to membrane‐active antimicrobial cyclodextrin (CD) development. CDs contain polyalkylamino groups; molecule polyfunctionalization was achieved via a click reaction. A survey using CDs with systematically varied functionalities clarified the unique correlation of their antimicrobial activity with the molecules’ hydrophobicity/hydrophilicity balance. The optimum hydrophobicity of the membrane‐active molecule was specific to bacterial strains and animal cells, leading to selective toxicity against bacteria including multidrug‐resistant bacteria such as methicillin‐resistant Staphylococcus aureus . The results demonstrate that CDs have a good molecular scaffold to pursue rationally designed structures with a desired activity for new antibiotic development.