title: Design, synthesis, and antimicrobial evaluation of hexadentate hydroxypyridinones with high iron(III) affinity.
abstract: 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 (logK1 ) were determined to be over 34, and pFe 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 μg/mL, respectively. These results indicate that hexadentate 3-hydroxypyridin-4-ones have potential application as antimicrobial agents, especially in the treatment of wound infection.
authors.affiliation: School of Food Science and Biotechnology, Zhejiang Gongshang University, Hangzhou, Zhejiang, 310018, P. R. China.
authors.forename: Ming-Xia
authors.initials: MX
authors.lastname: Zhang
authors.forename: Chun-Feng
authors.initials: CF
authors.lastname: Zhu
authors.forename: Ying-Jun
authors.initials: YJ
authors.lastname: Zhou
authors.forename: Xiao-Le
authors.initials: XL
authors.lastname: Kong
authors.forename: Robert C
authors.initials: RC
authors.lastname: Hider
authors.forename: Tao
authors.initials: T
authors.lastname: Zhou
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D015195:Drug Design; D005290:Ferric Compounds / Q000737:chemistry*; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D006207:Half-Life; D008826:Microbial Sensitivity Tests; D009539:Nicotinic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000081:Acetamides; D000890:Anti-Infective Agents; D005290:Ferric Compounds; D009539:Nicotinic Acids; D011725:Pyridines; D011728:Pyridones; C506370:hexadentate 3-hydroxypyridin-4-one
keywords: antimicrobial activity; hexadentate; hydroxypyridinone; iron affinity; iron chelator