Issue 38, 2023, Issue in Progress

A BODIPY-picolinium-cation conjugate as a blue-light-responsive caged group

Abstract

Caged compounds protected with photolabile protecting groups (PPGs) are useful for controlling various biological events with high spatiotemporal resolution. Most of the commonly used PPGs are controlled by ultraviolet light irradiation, but it is desirable to have PPGs controlled by visible light irradiation in order to minimize tissue damage. Here, we describe a boron-dipyrromethene (BODIPY)-picolinium conjugate (BPc group) that functions as a blue-light-controllable PPG. ESR experiments indicate that the photolysis mechanism is based on intramolecular photoinduced electron transfer. We illustrate the applicability of the BPc group to biologically active compounds by employing it firstly to photocontrol release of histamine, and secondly to photocontrol release of a soluble guanylyl cyclase (sGC) activator, GSK2181236A, which induces photovasodilation. The BPc group is expected to be a useful PPG for controlling various biological events with blue light irradiation.

Graphical abstract: A BODIPY-picolinium-cation conjugate as a blue-light-responsive caged group

Supplementary files

Article information

Article type
Paper
Submitted
08 Jun 2023
Accepted
20 Aug 2023
First published
04 Sep 2023
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2023,13, 26375-26379

A BODIPY-picolinium-cation conjugate as a blue-light-responsive caged group

N. Ieda, A. Nakamura, N. Tomita, K. Ohkubo, R. Izumi, Y. Hotta, M. Kawaguchi, K. Kimura and H. Nakagawa, RSC Adv., 2023, 13, 26375 DOI: 10.1039/D3RA03826B

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