Abstract
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.
Highlights
Nitric oxide (NO) is an endogenous regulator of various physiological events, including vasodilation, immune response, and neural transmission[1,2,3,4]
We previously developed intramolecular photoinduced electron transfer (PeT)-triggered nitric oxide (NO) releasers consisting of N-nitrosoaminophenol as the NO-releasing moiety and a visible-light-harvesting dye as the antenna moiety (Fig. 1a)
Spectroscopic studies indicated that a proximity effect, probably through π-π stacking, could significantly improve the NO-releasing efficiency of our PeT-triggered NO releasers in response to yellowish-green photoirradiation
Summary
Nitric oxide (NO) is an endogenous regulator of various physiological events, including vasodilation, immune response, and neural transmission[1,2,3,4]. This phenoxyl radical is unstable, and the N-N bond is cleaved homolytically to release relatively stable NO and quinoneimine[13]. The aim of the present work was to synthesize a series of NO-Rosa[1] derivatives in order to investigate the structure-efficiency relationship of PeT-triggered NO release in response to yellowish-green light irradiation. We found that O-alkylation of the NO-releasing moiety blocked NO release by changing the photodecomposition pathway We further utilized these findings to develop a double-lock system employing both enzymatic reactivation and photo-control to intend highly specific regulation of NO release
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