Rational Design of Latent Fluorophores from Water‐Soluble Hydroxyphenyltriazine Dyes Suitable for Lipase Sensing. Issue 8 (3rd February 2015)

• Record Type: Journal Article
• Authors: Jacquemet, Alicia; Rihn, Sandra; Ulrich, Gilles; Renard, Pierre‐Yves; Romieu, Anthony; Ziessel, Raymond
• Is Part Of: European journal of organic chemistry. Issue 8(2015)
• Page Start: 1664
• Page End: 1669
• Publication Date: 2015-02-03
• Subjects: Dyes/pigments -- Proton transfer -- Fluorophores -- Enzymes -- Protecting groups; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500047
• Languages: English
• ISSNs: 1434-193X

Abstract

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 (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. Abstract : 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.