title: Evaluation of (acyloxy)alkyl ester linkers for antibiotic release from siderophore-antibiotic conjugates.
abstract: The syntheses of five ciprofloxacin-modified (acyloxyl)alkyl esters and two siderophore-ciprofloxacin conjugates based on enterobactin that harbor such hydrolyzable linkages are reported. The hydrolytic stabilities of ciprofloxacin-modified (acyloxy)alkyl esters, evaluated at pH 7.5 and 30°C, vary by >370-fold depending on the substituents in the vicinity of the ester linkage.
authors: Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue 16-573B, Cambridge, MA 02139, USA.
authors: Tengfei
authors: T
authors: Zheng
authors: Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue 16-573B, Cambridge, MA 02139, USA. Electronic address: lnolan@mit.edu.
authors: Elizabeth M
authors: EM
authors: Nolan
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002939:Ciprofloxacin / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D048168:Escherichia coli K12 / Q000187:drug effects*; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006868:Hydrolysis; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011550:Pseudomonas aeruginosa / Q000187:drug effects*; D017262:Siderophores / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D004952:Esters; D017262:Siderophores; D002939:Ciprofloxacin
keywords: Antibiotic delivery; Linker stability; Siderophore