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.