Development of ratiometric carbohydrate sensor based on boron dipyrromethene (BODIPY) scaffold

Nusaiba Madappuram Cheruthu, Toru Komatsu, Tasuku Ueno, Kenjiro Hanaoka, Yasuteru Urano

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

We designed a ratiometric carbohydrate sensor consisting of the boron dipyrromethene fluorophore substituted with boronic acid at the 2-position, based upon the strong substituent dependency of the absorbance/fluorescence wavelengths of BODIPY. The substituent is in equilibrium between the boronic acid B(OH)2 and boronate (B(OH)3 ) forms, which have different absorbance/fluorescence wavelengths in the visible region. Reaction of the boronic acid moiety with hydroxy groups of carbohydrate affords a cyclic ester and shifts the equilibrium in favor of the boronate (B(OR)3 ) form, resulting in a carbohydrate-concentration-dependent change of the fluorescence ratio. Thus, the sensor, BA-BODIPY, can ratiometrically detect carbohydrate at a pH near the pKa of cyclic ester formation.

Original languageEnglish
Article number126684
JournalBioorganic and Medicinal Chemistry Letters
Volume29
Issue number22
DOIs
Publication statusPublished - 2019 Nov 15
Externally publishedYes

Keywords

  • Boron dipyrromethene (BODIPY)
  • Carbohydrates
  • Chemical biology
  • Fluorescent sensor

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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