Synthesis and evaluation of novel O2-derived diazeniumdiolates as photochemical and real-time monitoring nitric oxide delivery agents

Xiaojun Luo; Jianbing Wu; Tian Lv; Yisheng Lai; Honghua Zhang; Jin-Jian Lu; Yihua Zhang; Zhangjian Huang

doi:10.1039/C7QO00695K

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Synthesis and evaluation of novel O²-derived diazeniumdiolates as photochemical and real-time monitoring nitric oxide delivery agents†

Xiaojun Luo,^a Jianbing Wu,^a Tian Lv,^a Yisheng Lai,^a Honghua Zhang,^b Jin-Jian Lu,

^c Yihua Zhang

^a and Zhangjian Huang

*^a

Author affiliations

* Corresponding authors

^a State Key Laboratory of Natural Medicines, Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases, Jiangsu Key Laboratory of Drug Screening, China Pharmaceutical University, Nanjing 210009, PR China
E-mail: zhangjianhuang@cpu.edu.cn

^b Foreign Languages Department, China Pharmaceutical University, Nanjing 210009, PR China

^c State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences, University of Macau, Macao, China

Abstract

A group of photochemical nitric oxide (NO) delivery agents, O²-(4-hydroxyphenacyl) diazeniumdiolates 1–2 as well as O²-(3-(benzothiazole-2-yl)-4-hydroxyphenacyl) diazeniumdiolates 3–4, could be triggered by ultraviolet light (365–400 nm) and visible light (≥410 nm), respectively, to produce NO in cancer cells and generate potent antitumor activity. Importantly, with the photolysis of 3 being initiated, the accompanying distinct fluorescence color change (from green to blue) may act as a qualitative real-time optical indicator for NO release in cancer cells.

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Article information

DOI: https://doi.org/10.1039/C7QO00695K
Article type: Research Article
Submitted: 05 Aug 2017
Accepted: 05 Sep 2017
First published: 06 Sep 2017

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Org. Chem. Front., 2017,4, 2445-2449

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Synthesis and evaluation of novel O²-derived diazeniumdiolates as photochemical and real-time monitoring nitric oxide delivery agents

X. Luo, J. Wu, T. Lv, Y. Lai, H. Zhang, J. Lu, Y. Zhang and Z. Huang, Org. Chem. Front., 2017, 4, 2445 DOI: 10.1039/C7QO00695K

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