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Design, Synthesis, and Antimicrobial Evaluation of Hexadentate Hydroxypyridinones with High Iron( III ) Affinity
Author(s) -
Zhang MingXia,
Zhu ChunFeng,
Zhou YingJun,
Kong XiaoLe,
Hider Robert C,
Zhou Tao
Publication year - 2014
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.12358
Subject(s) - antimicrobial , chemistry , bacillus subtilis , pseudomonas aeruginosa , escherichia coli , minimum inhibitory concentration , bacteria , antibacterial activity , microbiology and biotechnology , biochemistry , biology , organic chemistry , gene , genetics
A range of hexadentate 3‐hydroxypyridin‐4‐ones (HPOs) with high affinity for iron(III) has been synthesized. The log stability constants of two HPO–iron complexes (logK 1 ) were determined to be over 34, and pF e values of the two HPOs were determined to be over 31. Antimicrobial assay indicated that they are able to markedly inhibit the growth of both Gram‐positive and Gram‐negative bacteria. Compounds 14a and 14e were found to exhibit the strongest inhibitory activity against Staphyloccocus aureus, Bacillus subtilis, Pseudomonas aeruginosa, and Escherichia coli, with MIC values of 8, 8, 16, and 8 μ g/mL, respectively. These results indicate that hexadentate 3‐hydroxypyridin‐4‐ones have potential application as antimicrobial agents, especially in the treatment of wound infection.