Blue and green light responsive caged glutamate

[Display omitted] •Single photon visible light responsive caged glutamate (Glu).•11 Examples reported that respond to 467 nm and 520–540 nm.•Two BODIPY derived cages reported for the first time.•Highest quantum yield (quantum efficiency) at 0.65. Glutamate (Glu) is an excitatory neurotransmitter tha...

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Bibliographic Details
Published in:Journal of photochemistry and photobiology. A, Chemistry. Chemistry., 2024-01, Vol.447, p.115183, Article 115183
Main Authors: Ma, Jingxuan, Egodawaththa, Nishal M., Guruge, Charitha, Valladares Márquez, Oriana A., Likes, Molly, Nesnas, Nasri
Format: Article
Language:English
Subjects:
BODIPY
Caged Glu
Glutamate
Photo-protecting group
Photoirradiation
Visible light
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Summary:[Display omitted] •Single photon visible light responsive caged glutamate (Glu).•11 Examples reported that respond to 467 nm and 520–540 nm.•Two BODIPY derived cages reported for the first time.•Highest quantum yield (quantum efficiency) at 0.65. Glutamate (Glu) is an excitatory neurotransmitter that plays a critical role in memory. Brain mapping activities of such pathways relied heavily on the ability to release Glu with spatiotemporal precision. Several photo-protecting groups (PPGs), referred to as photocages or cages, were designed to accomplish the release of Glu upon irradiation. Previously reported Glu cages responded to UV upon irradiation with single photons, which limited their use in vivo experiments due to cytotoxicity. Other caged designs suffered from lower quantum efficiency (QE) of release necessitating higher concentrations and/or longer photoirradiation times. There have been limited examples of cages that respond to visible light with single photon irradiation. Herein, we report the efficient preparation of 11 caged Glu examples that respond to two visible wavelengths, 467 nm (thiocoumarin based) and 515–540 nm (BODIPY based). The kinetics of photo-uncaging were studied for all caged designs, and we report all quantum efficiencies, i.e., quantum yields (Φ), that ranged from 0.0001 to 0.65. Two of the BODIPY cages are reported here for the first time, and one, Me-BODIPY-Br-Glu, shows the most efficient Glu release with a QE of 0.65. Similar caged designs can be extended to the inhibitory neurotransmitter, GABA. This would enable the use of two visible wavelengths to modulate the release of excitatory and inhibitory neurotransmitters upon demand via optical control.
ISSN:1010-6030
1873-2666
DOI:10.1016/j.jphotochem.2023.115183