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Photoactivatable fluorescein derivatives caged with a (3-hydroxy-2-naphthalenyl)methyl group.

ABSTRACT: The (3-hydroxy-2-naphthalenyl)methyl (NQMP) group represents an efficient photocage for fluorescein-based dyes. Thus, irradiation of the 6-NQMP ether of 2'-hydroxymethylfluorescein with low-intensity UVA light results in a 4-fold increase in emission intensity. Photoactivation of nonfluorescent NQMP-caged 3-allyloxyfluorescein produces a highly emissive fluorescein monoether. To facilitate conjugation of the caged dye to the substrate of interest via click chemistry, the allyloxy appendage was functionalized with an azide moiety.

SUBMITTER: Nekongo EE

PROVIDER: S-EPMC5991796 | biostudies-literature | 2014 Aug

REPOSITORIES: biostudies-literature

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Photoactivatable fluorescein derivatives caged with a (3-hydroxy-2-naphthalenyl)methyl group.

Nekongo Emmanuel E EE Popik Vladimir V VV

The Journal of organic chemistry 20140801 16

The (3-hydroxy-2-naphthalenyl)methyl (NQMP) group represents an efficient photocage for fluorescein-based dyes. Thus, irradiation of the 6-NQMP ether of 2'-hydroxymethylfluorescein with low-intensity UVA light results in a 4-fold increase in emission intensity. Photoactivation of nonfluorescent NQMP-caged 3-allyloxyfluorescein produces a highly emissive fluorescein monoether. To facilitate conjugation of the caged dye to the substrate of interest via click chemistry, the allyloxy appendage was f ...[more]

PMID: 25036698

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