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

Author:

Panfilov Mikhail A.12,Karogodina Tatyana Yu.12,Sibiryakova Anastasiya A.1,Tretyakova Irina S.34,Vorob'ev Alexey Yu.12,Moskalensky Alexander E.1ORCID

Affiliation:

1. Novosibirsk State University Novosibirsk 630090 Russia

2. N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS Novosibirsk 630090 Russia

3. Institute of Chemical Kinetics and Combustion SB RAS Novosibirsk 630090 Russia

4. Institute of Solid State Chemistry and Mechanochemistry SB RAS Novosibirsk 630090 Russia

Abstract

AbstractNitric 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.

Funder

Russian Science Foundation

Publisher

Wiley

Subject

General Chemistry

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