- Multi-target-directed ligands for treating Alzheimer's disease: Butyrylcholinesterase inhibitors displaying antioxidant and neuroprotective activities
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The limited clinical efficacy of current symptomatic treatment and minute effect on progression of Alzheimer's disease has shifted the research focus from single targets towards multi-target-directed ligands. Here, a potent selective inhibitor of human bu
- Knez, Damijan,Coquelle, Nicolas,Pi?lar, Anja,?akelj, Simon,Juki?, Marko,Sova, Matej,Mravljak, Janez,Nachon, Florian,Brazzolotto, Xavier,Kos, Janko,Colletier, Jacques-Philippe,Gobec, Stanislav
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- Synthesis and Characterization of Anguibactin to Reveal Its Competence to Function as a Thermally Stable Surrogate Siderophore for a Gram-Negative Pathogen, Acinetobacter baumannii
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Total synthesis of anguibactin was accomplished for the first time, and the following biochemical characterizations allowed for the determination of its Fe(III) binding mode as well as the demonstration of its iron delivery capability for Acinetobacter ba
- Lee, Haeun,Song, Woon Young,Kim, Minju,Lee, Min Wook,Kim, Soojeung,Park, Ye Song,Kwak, Kyungwon,Oh, Man Hwan,Kim, Hak Joong
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- Evaluation of desferrithiocin and its synthetic analogues as orally effective iron chelators
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Desferrithiocin, a novel microbial siderophore isolatod from cultures of Streptomyces antibioticus DSM 1865, and a number of its derivatives and analogues are evaluated for their ability to promote iron clearance. The compounds have been designed with the
- Bergeron,Wiegand,Dionis,Egli-Karmakka,Frei,Huxley-Tencer,Peter
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- Pyochelin Biosynthetic Metabolites Bind Iron and Promote Growth in Pseudomonads Demonstrating Siderophore-like Activity
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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.
- Kaplan, Anna R.,Musaev, Djamaladdin G.,Wuest, William M.
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p. 544 - 551
(2021/03/03)
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- Design and synthesis of new 2-aryl-4,5-dihydro-thiazole analogues: In vitro antibacterial activities and preliminary mechanism of action
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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.
- Tan, Fangfang,Shi, Baojun,Li, Jian,Wu, Wenjun,Zhang, Jiwen
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p. 20118 - 20130
(2015/12/23)
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- Synthesis and biological properties of thiazole-analogues of pyochelin, a siderophore of Pseudomonas aeruginosa
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Pyochelin is a siderophore common to all strains of Pseudomonas aeruginosa utilized by this Gram-negative bacterium to acquire iron(III). FptA is the outer membrane transporter responsible of ferric-pyochelin uptake in P. aeruginosa. We describe in this Letter the synthesis and the biological properties ( 55Fe uptake, binding to FptA) of several thiazole analogues of pyochelin. Among them we report in this Letter the two first pyochelin analogues able to bind FptA without promoting any iron uptake in P. aeruginosa.
- No?l, Sabrina,Hoegy, Fran?oise,Rivault, Freddy,Rognan, Didier,Schalk, Isabelle J.,Mislin, Ga?tan L.A.
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p. 132 - 135
(2014/01/17)
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- 2-Substituted 4,5-dihydrothiazole-4-carboxylic acids are novel inhibitors of metallo-β-lactamases
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Bacterial resistance to β-lactam antibiotics caused by class B metallo-β-lactamases (MBL), especially for certain hospital-acquired, Gram-negative pathogens, poses a significant threat to public health. We report several 2-substituted 4,5-dihydrothiazole-4-carboxylic acids to be novel MBL inhibitors. Structure activity relationship (SAR) and molecular modeling studies were performed and implications for further inhibitor design are discussed.
- Chen, Pinhong,Horton, Lori B.,Mikulski, Rose L.,Deng, Lisheng,Sundriyal, Sandeep,Palzkill, Timothy,Song, Yongcheng
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supporting information
p. 6229 - 6232
(2012/10/29)
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- Bacterial siderophores: Synthesis and biological activities of novel pyochelin analogues
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The synthesis and biological activities of four pyochelin analogues substituted in different parts of the molecule are reported: 5-NHBoc-pyochelin, 3″N-Boc-pyochelin, 3″-nor-NH-pyochelin and neopyochelin II, the enantiomer of natural pyochelin. All these
- Zamri,Schalk,Pattus,Abdallah
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p. 1147 - 1150
(2007/10/03)
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- Approaches to the high-throughput synthesis of analogues of dihydroaertiginoic acid
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A solution-phase synthesis of dihydroaeruginoic acid (1) was identified for its application towards the high-throughput synthesis of analogues of dihydroaeruginoic acid (1). Development of a solid-phase synthesis of dihydroaeruginoic acid (1) was examined
- Loughlin, Wendy A.,Knevitt, Scott A.,Hashing, Rachel E.,Marshall, Raymond L.
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p. 457 - 462
(2007/10/03)
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- An improved stereocontrolled synthesis of pyochelin, siderophore of Pseudomonas aeruginosa and Burkholderia cepacia
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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.
- Zamri, Adel,Abdallah, Mohamed A.
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p. 249 - 256
(2007/10/03)
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