1154500-34-1Relevant articles and documents
Study of iron piperazine-based chelators as potential siderophore mimetics
Loupias, Pauline,Dechamps-Olivier, Isabelle,Dupont, Laurent,Vanlemmens, Pierre,Mullié, Catherine,Taudon, Nicolas,Bouchut, Anne,Dassonville-Klimpt, Alexandra,Sonnet, Pascal
, (2019)
Gram-negative bacteria’s resistance such as Pseudomonas aeruginosa and the Burkholderia group to conventional antibiotics leads to therapeutic failure. Use of siderophores as Trojan horses to internalize antibacterial agents or toxic metals within bacteria is a promising strategy to overcome resistance phenomenon. To combat the Pseudomonas sp, we have synthesized and studied two piperazine-based siderophore mimetics carrying either catecholate moieties (1) or hydroxypyridinone groups (2) as iron chelators. These siderophore-like molecules were prepared in no more than four steps with good global yields. The physicochemical study has highlighted a strong iron affinity since their pFe values were higher than 20. 1 possesses even a pFe value superior than those of pyoverdine, the P. aeruginosa endogenous siderophore, suggesting its potential ability to compete with it. At physiological pH, 1 forms mainly a 2:3 complex with iron, whereas two species are observed for 2. Unfortunately, the corresponding Ga(III)-1 and 2 complexes showed no antibacterial activity against P. aeruginosa DSM 1117 strain. The evaluation of their siderophore-like activity showed that 1 and 2 could be internalized by the bacteria.
Cefiderocol (S-649266), A new siderophore cephalosporin exhibiting potent activities against Pseudomonas aeruginosa and other gram-negative pathogens including multi-drug resistant bacteria: Structure activity relationship
Aoki, Toshiaki,Yoshizawa, Hidenori,Yamawaki, Kenji,Yokoo, Katsuki,Sato, Jun,Hisakawa, Shinya,Hasegawa, Yasushi,Kusano, Hiroki,Sano, Masayuki,Sugimoto, Hideki,Nishitani, Yasuhiro,Sato, Takafumi,Tsuji, Masakatsu,Nakamura, Rio,Nishikawa, Toru,Yamano, Yoshinori
supporting information, p. 847 - 868 (2018/07/03)
The structure-activity relationship (SAR) for a novel series of catechol conjugated siderophore cephalosporins is described with their in vitro activities against multi-drug resistant Gram-negative pathogens including Pseudomonas aeruginosa, Acinetobacter baumannii, Stenotrophomonas maltophilia and Enterobacteriaceae. Cefiderocol (3) was one of the best molecules which displayed well-balanced and potent activities against multi-drug resistant Gram-negative pathogens including carbapenem resistant bacteria among the prepared compounds with the modified C-7 side chain and the modified C-3 side chain. Cefiderocol (3) is a highly promising parenteral cephalosporin for the treatment of multi-drug resistant Gram-negative infection.
Vibriobactin antibodies: A vaccine strategy
Bergeron, Raymond J.,Bharti, Neelam,Singh, Shailendra,McManis, James S.,Wiegand, Jan,Green, Linda G.
experimental part, p. 3801 - 3813 (2010/04/24)
A new target strategy in the development of bacterial vaccines, the induction of antibodies to microbial outer membrane ferrisiderophore complexes, is explored. A vibriobactin (VIB) analogue, with a thiol tether, 1-(2,3-dihydroxybenzoyl)-5,9-bis[[(4S,5R)-
