Evaluation of (acyloxy)alkyl ester linkers for antibiotic release from siderophore-antibiotic conjugates

Bioorganic & Medicinal Chemistry Letters
Tengfei Zheng, Elizabeth M Nolan

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.

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Citations

Jun 25, 2016·Nanomedicine : Nanotechnology, Biology, and Medicine·Andrzej S SkwareckiMaria J Milewska
Aug 6, 2016·Organic & Biomolecular Chemistry·Colette KurthMarkus Nett
Sep 14, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kokob H NegashJames T Hodgkinson
Mar 29, 2019·Biometals : an International Journal on the Role of Metal Ions in Biology, Biochemistry, and Medicine·Yun-Ming LinMarvin J Miller
Jul 4, 2018·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Wilma Neumann, Elizabeth M Nolan
Jul 10, 2018·Monatshefte für chemie·Joanna Fedorowicz, Jarosław Sączewski
Aug 23, 2019·European Journal of Medicinal Chemistry·Huimin KongXiaojian Zhang
Dec 11, 2020·Journal of the American Chemical Society·Jonathan H BoyceIan B Seiple
Jun 11, 2021·ACS Infectious Diseases·Tabbetha J BohacTimothy A Wencewicz
Oct 17, 2020·Journal of Pharmaceutical Sciences·Mai ShimizuMiki Nakajima
Sep 29, 2017·Journal of the American Chemical Society·Timothy C Johnstone, Elizabeth M Nolan

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