Activatable fluorescent probes for hydrolase enzymes based on coumarin-hemicyanine hybrid fluorophores with large Stokes shifts

Hiroyoshi Fujioka; Shin-Nosuke Uno; Mako Kamiya; Ryosuke Kojima; Kai Johnsson; Yasuteru Urano

doi:10.1039/d0cc00559b

Activatable fluorescent probes for hydrolase enzymes based on coumarin-hemicyanine hybrid fluorophores with large Stokes shifts

Chem Commun (Camb). 2020 May 27;56(42):5617-5620. doi: 10.1039/d0cc00559b.

Authors

Hiroyoshi Fujioka¹, Shin-Nosuke Uno², Mako Kamiya³, Ryosuke Kojima³, Kai Johnsson⁴, Yasuteru Urano⁵

Affiliations

¹ Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. [email protected].
² Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. [email protected] and Institute of Chemical Sciences and Engineering (ISIC), École Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, Switzerland.
³ Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
⁴ Institute of Chemical Sciences and Engineering (ISIC), École Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne, Switzerland and Department of Chemical Biology, Max Planck Institute for Medical Research, Jahnstrasse 29, 69120 Heidelberg, Germany. [email protected].
⁵ Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. [email protected] and Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan and CREST (Japan) Agency for Medical Research and Development (AMED), 1-7-1 Otemachi, Chiyoda-ku, Tokyo 100-0004, Japan.

PMID: 32297612
DOI: 10.1039/d0cc00559b

Abstract

We show that the equilibrium of intramolecular spirocyclization of coumarin-hemicyanine hybrid fluorophores can be finely tuned by means of chemical modifications. We used this scaffold to develop activatable fluorescent probes with large Stokes shifts for γ-glutamyltranspeptidase and esterase.

MeSH terms

A549 Cells
Coumarins / chemistry*
Coumarins / metabolism
Esterases / analysis*
Esterases / metabolism
Esters / chemistry*
Esters / metabolism
Fluorescent Dyes / chemistry*
Fluorescent Dyes / metabolism
Humans
Hydrolysis
Indoles / chemistry*
Indoles / metabolism
Spectrometry, Fluorescence / methods

Substances

Coumarins
Esters
Fluorescent Dyes
Indoles
Esterases