27266-61-1Relevant articles and documents
Specific detection ofIMP-1β-lactamase activity using atranscephalosporin-based fluorogenic probe
Chen, Fangfang,Hu, Liqiang,Li, Ziyao,Liu, Runqiu,Ma, Zheng,Xie, Hexin,Yu, Tao,Yuan, Chang,Zou, Yingqiu
supporting information, p. 13586 - 13589 (2021/12/23)
A fluorogenic probe for the specific detection ofIMP-1β-lactamase activity has been developed. This imaging reagent features a uniquetrans-acetylamino cephalosporin as an enzymatic recognition moiety, exhibiting excellent selectivity toIMP-1β-lactamase ov
Toward the development of a cephalosporin-based dual-release prodrug for use in ADEPT
Grant, Jonathan W.,Smyth, Timothy P.
, p. 7965 - 7970 (2007/10/03)
In previous work we have shown that a cephalosporin structure bearing an S-aminosulfenimine at the 7-position behaved as a β-lactamase-dependent dual-release prodrug. Scission of the β-lactam ring of such a structure led to the rapid loss of the sulfur-at
Antimicrobial effects of novel siderophores linked to β-lactam antibiotics
Kline,Fromhold,McKennon,Cai,Treiberg,Ihle,Sherman,Schwan,Hickey,Warrener,Witte,Brody,Goltry,Barker,Anderson,Tanaka,Shawar,Nguyen,Langhorne,Bigelow,Embuscado,Naeemi
, p. 73 - 93 (2007/10/03)
As a strategy to increase the penetration of antibiotic drugs through the outer membrane of Gram-negative pathogens, facilitated transport through siderophore receptors has been frequently exploited. Hydroxamic acids, catechols, or very close isosteres of catechols, which are mimics of naturally occurring siderophores, have been used successfully as covalently linked escorting moieties, but a much wider diversity of iron binding motifs exists. This observation, coupled to the relative lack of specificity of siderophore receptors, prompted us to initiate a program to identify novel, noncatechol siderophoric structures. We screened over 300 compounds for their ability to (1) support growth in low iron medium of a Pseudomonas aeruginosa siderophore biosynthesis deletion mutant, or (2) compete with a bactericidal siderophore-antibiotic conjugate for siderophore receptor access. From these assays we identified a set of small molecules that fulfilled one or both of these criteria. We then synthesized these compounds with functional groups suitable for attachment to both monobactam and cephalosporin core structures. Siderophore-β-lactam conjugates then were tested against a panel of Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus strains. Although several of the resultant chimeric compounds had antimicrobial activity approaching that of ceftazidime, and most compounds demonstrated very potent activity against their cellular targets, only a single compound was obtained that had enhanced, siderophore-mediated antibacterial activity. Results with tonB mutants frequently showed increased rather than decreased susceptibilities, suggesting that multiple factors influenced the intracellular concentration of the drugs. (C) 2000 Elsevier Science Ltd.
