Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1, Tanabe-dori, Mizuho-ku, Nagoya, Aichi, 467-8603, Japan.
Faculty of Pharmaceutical Sciences, Nagoya City University, 3-1, Tanabe-dori, Mizuho-ku, Nagoya, Aichi, 467-8603, Japan.
Sci Rep. 2019 Feb 5;9(1):1430. doi: 10.1038/s41598-018-38252-5.
Spatiotemporally controllable nitric oxide (NO) releasers are required for biological studies and as candidate therapeutic agents. Here, we investigate the structure-efficiency relationship of a series of photoinduced electron transfer-triggered NO releasers based on our reported yellowish-green light-controllable NO releaser, NO-Rosa. The distance between the NO-releasing N-nitrosoaminophenol moiety and the rosamine antenna moiety was critical for efficient NO release. Notably, substitution at the phenolic hydroxyl group blocked NO release. We synthesized NO-Rosa-Gal bearing D-galactose (Gal) at this location, and showed that hydrolysis by β-galactosidase restored the photoresponse. This represents proof-of-concept of a strategy for highly specific control of NO release by using a double-lock system involving both enzymatic reactivation and photo-control.
时空可控的一氧化氮（NO）释放剂是生物研究和候选治疗药物所必需的。在这里，我们根据我们之前报道的基于黄绿光控制的 NO 释放剂NO-Rosa，研究了一系列光诱导电子转移触发的 NO 释放剂的结构-效率关系。NO 释放的 N-亚硝基氨基苯酚部分和若丹明天线部分之间的距离对于高效的 NO 释放至关重要。值得注意的是，在酚羟基上的取代阻止了 NO 的释放。我们在这个位置合成了带有 D-半乳糖（Gal）的 NO-Rosa-Gal，并表明β-半乳糖苷酶的水解恢复了光响应。这代表了一种通过使用涉及酶复活和光控制的双重锁定系统来高度特异性控制 NO 释放的策略的概念验证。
