title: β-Galactosidase fluorescence probe with improved cellular accumulation based on a spirocyclized rhodol scaffold.
abstract: We identified a rhodol bearing a hydroxymethyl group (HMDER) as a suitable scaffold for designing fluorescence probes for various hydrolases. HMDER shows strong fluorescence at physiological pH, but phenolic O-alkylation of HMDER results in a strong preference for the spirocyclic form, which has weak fluorescence. As a proof of concept, we utilized this finding to develop a new fluorescence probe for β-galactosidase. This probe has favorable characteristics for imaging in biological samples: it has good cellular permeability, and its hydrolysis product is well-retained intracellularly. It could rapidly and clearly visualize β-galactosidase activity in cultured cells and in Drosophila melanogaster tissue, which has rarely been achieved with previously reported fluorescence probes.
authors.affiliation: Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
authors.forename: Mako
authors.initials: M
authors.lastname: Kamiya
authors.forename: Daisuke
authors.initials: D
authors.lastname: Asanuma
authors.forename: Erina
authors.initials: E
authors.lastname: Kuranaga
authors.forename: Asuka
authors.initials: A
authors.lastname: Takeishi
authors.forename: Masayo
authors.initials: M
authors.lastname: Sakabe
authors.forename: Masayuki
authors.initials: M
authors.lastname: Miura
authors.forename: Tetsuo
authors.initials: T
authors.lastname: Nagano
authors.forename: Yasuteru
authors.initials: Y
authors.lastname: Urano
mesh_terms: D000818:Animals; D002463:Cell Membrane Permeability; D002478:Cells, Cultured; D003500:Cyclization; D004331:Drosophila melanogaster; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry* / Q000493:pharmacokinetics; D013141:Spiro Compounds / Q000737:chemistry; D001616:beta-Galactosidase / Q000032:analysis*
chemical_list: D005456:Fluorescent Dyes; D013141:Spiro Compounds; D001616:beta-Galactosidase