115921-07-8Relevant articles and documents
Pyochelin Biosynthetic Metabolites Bind Iron and Promote Growth in Pseudomonads Demonstrating Siderophore-like Activity
Kaplan, Anna R.,Musaev, Djamaladdin G.,Wuest, William M.
, p. 544 - 551 (2021/03/03)
Pseudomonads employ several strategies to sequester iron vital for their survival including the use of siderophores such as pyoverdine and pyochelin. Similar in structure but significantly less studied are pyochelin biosynthetic byproducts, dihydroaeruginoic acid, aeruginoic acid, aeruginaldehyde (IQS), and aeruginol, along with two other structurally related molecules, aerugine and pyonitrins A-D, which have all been isolated from numerous Pseudomonad extracts. Because of the analogous substructure of these compounds to pyochelin, we hypothesized that they may play a role in iron homeostasis or have a biological effect on other bacterial species. Herein, we discuss the physiochemical evaluation of these molecules and disclose, for the first time, their ability to bind iron and promote growth in Pseudomonads.
Design and synthesis of new 2-aryl-4,5-dihydro-thiazole analogues: In vitro antibacterial activities and preliminary mechanism of action
Tan, Fangfang,Shi, Baojun,Li, Jian,Wu, Wenjun,Zhang, Jiwen
, p. 20118 - 20130 (2015/12/23)
Sixty 2-aryl-4,5-dihydrothiazoles were designed and synthesized in yields ranging from 64% to 89% from cysteine and substituted-benzonitriles via a novel metal- and catalyst-free method. The structures of the title compounds were confirmed mainly by NMR spectral data analysis. Antibacterial activity assays showed that the compounds (S)-2-(2′-hydroxyphenyl)-4-hydroxy-methyl-4,5-dihydrothiazole (7h) and (R)-2-(2′-hydroxyphenyl)-4-hydroxymethyl-4,5-dihydro-thiazole (7h′) exhibited significant inhibition against Ralstonia solanacearum, Pseudomonas syringae pv. actinidiae, Bacillus subtilis and Bacillus cereus, with minimum inhibitory concentrations (MICs) ranging from 3.91 to 31.24 μg·mL-1. The effect of substituents showed that not only electron-withdrawing groups, but also electron-donating groups could abolish the antibacterial activities unless a 2′-hydroxy group was introduced on the 2-aryl substituent of the 4,5-dihydrothiazole analogues. The results of scanning electron microscope (SEM) and fatty acid exposure experiments indicated that these antibacterial compounds influence fatty acid synthesis in the tested bacteria.
An improved stereocontrolled synthesis of pyochelin, siderophore of Pseudomonas aeruginosa and Burkholderia cepacia
Zamri, Adel,Abdallah, Mohamed A.
, p. 249 - 256 (2007/10/03)
A considerably improved stereocontrolled synthesis of pyochelin, a hydroxyphenylthiazolinylthiazolidine type of siderophore common to most strains of Pseudomonas aeruginosa and Burkholderia cepacia is described. 2'- (2-Hydroxyphenyl)-2'-thiazoline-4'-carboxaldehyde, a key molecule involved in this synthesis has been prepared by reduction of 2'-(2-hydroxyphenyl)-2'- thiazoline-4'-(N-methoxy,N-methyl) carboxamide with lithium aluminium hydride. The aldehyde was further coupled with (R)-N-methylcysteine to yield pyochelin. Under the conditions reported, epimerization at the C-4' center was considerably diminished.
