A fluorogenic H2S-triggered prodrug based on thiolysis of the NBD amine

Yonghui Xie; Haojie Huang; Ismail Ismail; Hongyan Sun; Long Yi; Zhen Xi

doi:10.1016/j.bmcl.2019.126627

A fluorogenic H₂S-triggered prodrug based on thiolysis of the NBD amine

Bioorg Med Chem Lett. 2019 Oct 1;29(19):126627. doi: 10.1016/j.bmcl.2019.126627. Epub 2019 Aug 17.

Authors

Yonghui Xie¹, Haojie Huang², Ismail Ismail¹, Hongyan Sun³, Long Yi⁴, Zhen Xi⁵

Affiliations

¹ State Key Laboratory of Elemento-Organic Chemistry and Department of Chemical Biology, National Engineering Research Center of Pesticide (Tianjin), College of Chemistry, Nankai University, Tianjin 300071, China.
² State Key Laboratory of Organic-Inorganic Composites and Beijing Key Laboratory of Bioprocess, Beijing University of Chemical Technology (BUCT), Beijing 100029, China.
³ Department of Chemistry and Center of Super-Diamond and Advanced Films (COSDAF), City University of Hong Kong, 83 Tat Chee Avenue, Kowloon, Hong Kong, China; Key Laboratory of Biochip Technology, Biotech and Health Centre, Shenzhen Research Institute of City University of Hong Kong, Shenzhen, 518057, China.
⁴ State Key Laboratory of Organic-Inorganic Composites and Beijing Key Laboratory of Bioprocess, Beijing University of Chemical Technology (BUCT), Beijing 100029, China; Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), China. Electronic address: yilong@mail.buct.edu.cn.
⁵ State Key Laboratory of Elemento-Organic Chemistry and Department of Chemical Biology, National Engineering Research Center of Pesticide (Tianjin), College of Chemistry, Nankai University, Tianjin 300071, China; Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), China. Electronic address: zhenxi@nankai.edu.cn.

PMID: 31444083
DOI: 10.1016/j.bmcl.2019.126627

Abstract

Based on thiolysis of the NBD amine, a H₂S-triggered prodrug has been designed and synthesized for localized production of ciprofloxacin under micromolar H₂S. Activation of the prodrug can be monitored through fluorescence in real-time. We envision that thiolysis of the NBD amine could be readily used for development of other H₂S-triggered prodrugs in the future.

Keywords: Ciprofloxacin; H(2)S-triggered; NBD amine; Prodrug.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Air Pollutants / pharmacology
Amines / chemistry*
Anti-Bacterial Agents / pharmacology*
Ciprofloxacin / pharmacology*
Escherichia coli / drug effects*
Fluorescent Dyes
Hydrogen Sulfide / pharmacology*
Optical Imaging
Oxadiazoles / chemistry
Prodrugs / pharmacology*
Spectrometry, Fluorescence
Sulfhydryl Compounds / chemistry*

Substances

Air Pollutants
Amines
Anti-Bacterial Agents
Fluorescent Dyes
Oxadiazoles
Prodrugs
Sulfhydryl Compounds
Ciprofloxacin
Hydrogen Sulfide