Synthesis of a BODIPY Library and Its Application to the Development of Live Cell Glucagon Imaging Probe

被引:193
作者
Lee, Jun-Seok [1 ,2 ]
Kang, Nam-young [1 ]
Kim, Yun Kyung [1 ,2 ]
Samanta, Animesh [1 ]
Feng, Suihan [1 ,3 ]
Kim, Hyeong Kyu [1 ]
Vendrell, Marc [4 ]
Park, Jung Hwan [4 ]
Chang, Young-Tae [1 ,3 ,4 ]
机构
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
[2] NYU, Dept Chem, New York, NY 10003 USA
[3] Natl Univ Singapore, Inst Life Sci, MedChem Program, Singapore 117543, Singapore
[4] ASTAR, Singapore Bioimaging Consortium, Lab Bioimaging Probe Dev, Singapore 138667, Singapore
关键词
HUMAN SERUM-ALBUMIN; IN-VIVO; SPECTROSCOPIC PROPERTIES; COMBINATORIAL SYNTHESIS; FLUORESCENT SENSORS; ROSAMINE LIBRARY; ZINC IONS; DYES; CHEMOSENSORS; BIOLOGY;
D O I
10.1021/ja9011657
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first BODIPY library (BD) was synthesized, and a highly selective glucagon sensor, Glucagon Yellow (BD-105), was discovered by fluorescence image-based screening method. BD library was synthesized via a Knoevenagel-type condensation reaction with 160 benzaldehydes and the 1,3 dimethyl-BODIPY scaffold. Using BD compounds, a fluorescence image-based screening was performed against three cell lines including AlphaTC1 and BetaTC6 cells which secret glucagon and insulin, respectively, and HeLa as control cells. Out of the 160 candidate probes, one compound, Glucagon Yellow, exhibited selective staining only in AlphaTC1 cells. The selectivity of Glucagon Yellow toward glucagon was confirmed in vitro by comparison of its fluorescence intensity change against 19 biologically relevant analytes. Subsequent immunostaining experiments revealed that Glucagon Yellow and the glucagon antibody colocalized in pancreas tissue, showing a high quantitative correlation analysis by the Pearson's coefficient constant (R-r = 0.950). These results demonstrated the potential application of Glucagon Yellow as a glucagon imaging agent in live cells and tissues.
引用
收藏
页码:10077 / 10082
页数:6
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