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Rational Design of Latent Fluorophores from Water‐Soluble Hydroxyphenyltriazine Dyes Suitable for Lipase Sensing
Author(s) -
Jacquemet Alicia,
Rihn Sandra,
Ulrich Gilles,
Renard PierreYves,
Romieu Anthony,
Ziessel Raymond
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500047
Subject(s) - chemistry , fluorescence , moiety , intramolecular force , lipase , residue (chemistry) , phenol , stokes shift , phosphate buffered saline , photochemistry , combinatorial chemistry , organic chemistry , enzyme , chromatography , physics , quantum mechanics
Abstract 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 (Δ SS > 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.