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RESEARCH PRODUCT

Rational Design of Latent Fluorophores from Water-Soluble Hydroxyphenyltriazine Dyes Suitable for Lipase Sensing

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description

The phenol residue of water‐soluble 2‐(2′‐hydroxy‐5′‐dimethylaminobenzyl)‐4,6‐dimethylamino‐1,3,5‐triazine is masked by an enzyme‐labile protecting group constructed with a self‐immolative para‐hydroxybenzyl alcohol. The fluorescence of the dyes is restored with lipases under physiological conditions without aggregation or precipitation of the fluorescent dyes. Derivatives of 2‐(2′‐hydroxy‐5′‐dimethylaminobenzyl)‐4,6‐dimethylamino‐1,3,5‐triazine were synthesized by an original multistep protocol that afforded, after quaternization of the N,N‐dimethylaminobenzyl moiety, water‐soluble fluorescent dyes. These fluorophores exhibited excited‐state intramolecular proton transfer and large Stokes shifts (ΔSS > 10000 cm–1). The phenol residue was masked by an enzyme‐labile protecting group based on self‐immolative para‐hydroxybenzyl alcohol. Lipases were used to unveil the fluorescence under physiological conditions (phosphate‐buffered saline, pH 7.2) without aggregation or precipitation of the fluorescent dyes.