Meso‐Aminomethyl‐BODIPY as a Scaffold for Nitric Oxide Photo‐Releasers

Abstract

Nitric oxide (NO) is a unique biochemical mediator involved in the regulation of vital processes. Its short lifetime in physiological conditions and local action impede direct application in medicine because highly targeted NO‐delivery systems are required. Light‐controllable NO releasers are promising for the development of smart therapies. Here we present simply prepared meso‐aminomethyl BODIPY (4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene) derivatives containing N‐nitroso moiety, which show the photoinduced generation of NO in a solution. These compounds can additionally generate singlet oxygen, and NO/1O2 generation efficiency can be tuned by substituents. As an example of NO‐mediated effect, we demonstrate light‐dependent inhibition of platelet activation in vitro. The presented compounds could serve as the basis for the development of novel hybrid therapeutic methods.

Nitric Oxide Photorelease from Silicone Films Doped with N-Nitroso BODIPY

“…Figure 2C shows the resulting changes as follows, which are in agreement with the hypothesis: the maximal wavelength shifted from 517 to 514 nm, while the height of the spectra is almost unchanged. For the comparison, we reproduced the experiment in EtOH [32], where the spectral shift was accompanied by a decrease in optical density (Figure 2D). This is in agreement with the fact that ε for B1 is significantly higher than that for B0 in EtOH, while in PDMS, the extinction coefficients are almost the same.…”

“…We also used its analogue B0, which was synthesized independently for comparison with the photoproducts of B1. Synthesis of the compounds was done as described in [32]. Polymer film fabrication.…”

“…Extended work on BODIPY-based NO-releasing molecules was conducted by the Sortino group [29][30][31]. Several NO photodonors based on BODIPY [32] and aza-BODIPY [33] cores were developed by our group as well.…”

Recent Advancements in Polymeric N-Nitrosamine-Based Nitric Oxide (NO) Donors and their Therapeutic Applications

“…Another BODIPY-based N-nitrosamine was reported by Panfilov and co-workers, which exhibited NO release under exposure to 500 nm visible light. 71 Furthermore, the study revealed that the incorporation of heavy atoms such as iodine into the BODIPY moiety augmented the generation of photoinduced reactive oxygen species (ROS). However, these NO-releasing small molecules primarily facilitate NO release under visible light irradiation, which possesses restricted tissue penetration (<1 mm).…”