TY - JOUR
T1 - Development of ratiometric carbohydrate sensor based on boron dipyrromethene (BODIPY) scaffold
AU - Cheruthu, Nusaiba Madappuram
AU - Komatsu, Toru
AU - Ueno, Tasuku
AU - Hanaoka, Kenjiro
AU - Urano, Yasuteru
N1 - Funding Information:
This work was financially supported by MEXT ( 24655147 , 15H05371 , 15K14937 , 17K19477 , 18H04538 , and 19H02846 to T.K., and 16H05099 and 16H04609 to K.H.), ImPACT (Y.U.), JST (T.K. and K.H.), AMED (Y.U.), and JSPS (Core-to-Core Program, A. Advanced Research Networks). T.K. was supported by Naito Foundation , Mochida Memorial Foundation for Medical and Pharmaceutical Research , and The Tokyo Biochemical Research Foundation .
Publisher Copyright:
© 2019 Elsevier Ltd
PY - 2019/11/15
Y1 - 2019/11/15
N2 - 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.
AB - 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.
KW - Boron dipyrromethene (BODIPY)
KW - Carbohydrates
KW - Chemical biology
KW - Fluorescent sensor
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U2 - 10.1016/j.bmcl.2019.126684
DO - 10.1016/j.bmcl.2019.126684
M3 - Article
C2 - 31606347
AN - SCOPUS:85073034216
VL - 29
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
SN - 0960-894X
IS - 22
M1 - 126684
ER -