Okuno Hana, Ieda Naoya, Hotta Yuji, Kawaguchi Mitsuyasu, Kimura Kazunori, Nakagawa Hidehiko
Graduate School of Pharmaceutical Science, Nagoya City University, 3-1, Tanabe-dori, Mizuho-ku, Nagoya, Aichi 467-8603, Japan.
Org Biomol Chem. 2017 Mar 28;15(13):2791-2796. doi: 10.1039/c7ob00245a.
Nitric oxide (NO) has been known as a gaseous chemical mediator, which modulates several physiological functions. Spatial and temporal control of NO release facilitates further study and medical application of NO. Herein, we report design and synthesis of a novel NO donor, NO-Rosa. NO-Rosa has a rosamine moiety, which absorbs yellowish green light. Upon irradiation with yellowish green light (530-590 nm), NO is released from NO-Rosa, presumably via photoinduced electron transfer from the N-nitrosoaminophenol moiety to the rosamine moiety. NO release from NO-Rosa was detected by ESR spin trapping and a NO fluorescent probe. Cellular NO release control was achieved in HEK293 cells using a NO fluorescent probe, DAF-FM DA. Furthermore, temporally controlled NO-induced vasodilation was demonstrated by treatment of a rat aortic strip with NO-Rosaex vivo and irradiation by yellowish green light. NO-Rosa is expected to be utilized for further study of NO-related physiological functions, utilizing its ability of spatiotemporal release of NO as a photocontrollable compound with harmless yellowish-green light.
一氧化氮（NO）作为一种气态化学介质，可调节多种生理功能。对NO释放的空间和时间控制有助于对NO进行进一步研究和医学应用。在此，我们报告了一种新型NO供体NO-Rosa的设计与合成。NO-Rosa具有一个玫瑰胺部分，可吸收黄绿色光。在用黄绿色光（530 - 590 nm）照射时，NO从NO-Rosa释放，推测是通过从N-亚硝基氨基酚部分到玫瑰胺部分的光诱导电子转移实现的。通过电子顺磁共振（ESR）自旋捕获和NO荧光探针检测到了NO从NO-Rosa的释放。使用NO荧光探针DAF-FM DA在HEK293细胞中实现了细胞内NO释放的控制。此外，通过用NO-Rosa离体处理大鼠主动脉条并用黄绿色光照射，证明了时间可控的NO诱导的血管舒张。NO-Rosa有望作为一种利用无害黄绿色光进行时空释放NO的光控化合物，用于进一步研究与NO相关的生理功能。
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