Acta Pharm. 70 (2020) 483-498

 

full paper

Original research paper

 

Synthesis and evaluation of bisulfate/mesylate-conjugated chlortetracycline with high solubility and bioavailability

DENG LIU, PEIXING CHEN, XU YANG and JIANHUA WANG

jhwangcqu@gmail.com

Key Laboratory of Biorheological Science and Technology, Ministry of Education, Bioengineering College, Chongqing University, Chongqing, 400044, People’s Republic of China

Accepted February 24, 2020

Published online April 2, 2020

 

The aim of this work is to improve the solubility and bioavailability of chlortetracycline and the function of the immune response. Chlortetracycline bisulfate and chlortetracycline mesylate were successfully synthesized and characterized with several techniques, including spectroscopy, chromatography and mass spectrometry, which demonstrated that the C4-dimethylamino group of chlortetracycline can accept a proton from sulfuric acid and methanesulfonic acid to form the corresponding salts. In addition, chlortetracycline bisulfate and chlortetracycline mesylate were more soluble in water than chlortetracycline hydrochloride, but the antibacterial activity was not enhanced. The influences of chlortetracycline hydrochloride, chlortetracycline bisulfate and chlortetracycline mesylate on chlortetracycline and immunoglobulin concentrations in mouse serum were also investigated. These results suggested that the chlortetracycline bisulfate and chlortetracycline mesylate have good bioavailability and strong immune response and have potential applications in animal breeding and formulation technologies.

 

Keywords: chlortetracycline, pharmaceutical salt, solubility, bioavailability, antibacterial activity, immunoglobulin