β-galactosidase fluorescence probe with improved cellular accumulation based on a spirocyclized rhodol scaffold

Mako Kamiya, Daisuke Asanuma, Erina Kuranaga, Asuka Takeishi, Masayo Sakabe, Masayuki Miura, Tetsuo Nagano, Yasuteru Urano

Research output: Contribution to journalArticlepeer-review

145 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)12960-12963
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number33
DOIs
Publication statusPublished - 2011 Aug 24
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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