TY - JOUR

T1 - Meso-Aminomethyl-BODIPY as a Scaffold for Nitric Oxide Photo-Releasers

AU - Panfilov, Mikhail A.

AU - Karogodina, Tatyana Yu

AU - Sibiryakova, Anastasiya A.

AU - Tretyakova, Irina S.

AU - Vorob'ev, Alexey Yu

AU - Moskalensky, Alexander E.

N1 - The study was supported by the Russian Science Foundation (grant #18‐15‐00049).

PY - 2023/12/12

Y1 - 2023/12/12

N2 - 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.

AB - 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.

KW - BODIPY

KW - Nitric oxide

KW - photolabile “caged” nitric oxide

KW - photoremovable protecting group

KW - platelet activation

KW - singlet oxygen

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85178933870&origin=inward&txGid=63abee7638ec75ea1ba63fb86b2520d2

UR - https://www.mendeley.com/catalogue/11adb4a3-6f3a-35ef-be99-a3886f5723f7/

U2 - 10.1002/slct.202302681

DO - 10.1002/slct.202302681

M3 - Article

VL - 8

JO - ChemistrySelect

JF - ChemistrySelect

SN - 2365-6549

IS - 46

M1 - e202302681

ER -