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

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

研究成果: Article査読

4 被引用数 (Scopus)

抄録

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.

本文言語English
論文番号126684
ジャーナルBioorganic and Medicinal Chemistry Letters
29
22
DOI
出版ステータスPublished - 2019 11 15
外部発表はい

ASJC Scopus subject areas

  • 生化学
  • 分子医療
  • 分子生物学
  • 薬科学
  • 創薬
  • 臨床生化学
  • 有機化学

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