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Antenna Tuning in Photoredox Nitric Oxide Releasers for Potent Photovasodilation
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DOI：10.1021/acs.jmedchem.6c00784.png)
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Abstract
En 中文
To realize spatiotemporal control of nitric oxide (NO), a key signaling molecule for vasodilation in biological systems, we previously developed photocontrollable NO releasers such as NORD-1, whose NO release is triggered by photoinduced electron transfer (PeT) to a light-harvesting moiety. Here, we aimed to improve the PeT-driven NO release by investigating the structure–activity relationship of the rhodamine antenna, focusing on modifications of amino groups at the 3-/6-positions and the element at the 10-position. NO release from selenium- or tellurium-containing NO releasers (NO-SeR and NO-TeR) was significantly enhanced, whereas a phospharhodamine-type NO releaser (NO-POR) exhibited no detectable photodecomposition. Quantum-chemical calculations suggested that the charge-transfer state for NO-POR is stabilized compared to other NO releasers. We confirmed that NO-TeR showed more efficient vasodilation than NORD-1 in ex vivo studies. These findings are expected to facilitate the design of new PeT-driven compounds for biological and therapeutic applications.
Keywords:
Fluorescence
Heterocyclic compounds
Irradiation
Mixtures
Oxides
Journal
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6.8
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2.7W
Citations:
9.4W
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Cited Papers