1 research outputs found
Photosensitization of Fluorofuroxans and Its Application to the Development of Visible Light-Triggered Nitric Oxide Donor
Nitric
oxide (NO) is an endogenous signaling molecule used in multiple
biochemical processes. The development of switchable NO donors that
deliver an NO payload under spatiotemporal control harbors many medicinal
benefits. Previously, 4-fluorofuroxans were found to function as a
UV light-induced NO donor under physiological conditions based on
the photoinduced isomerization mechanism; however, the isomerization
of fluorofuroxans with longer wavelength light is desired for further
application into living systems. Herein, we report the use of photosensitizers
in the photochemical isomerization of fluorofuroxan, enabling the
use of visible light to induce isomerization. Among the tried photosensitizers,
anthraquinone derivatives showed a good sensitizing ability to isomerize
4-fluorofuroxan to 3-fluorofuroxan using visible light. This new phenomenon
was applied to the synthesis of a water-soluble anthraquinone-fluorofuroxan
all-in-one molecule, which demonstrated promising NO-releasing ability
using 400–500 nm irradiation. A high level of control is displayed
with “on” and “off” NO-release functionality
suggesting that photosensitizer-furoxan hybrids would make valuable
donors. Furthermore, unlike most furoxans, NO is released in the absence
of thiol cofactor