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

Jun-Seok Lee, Nam-young Kang, Yun Kyung Kim, Animesh Samanta, Suihan Feng, Hyeong Kyu Kim, Marc Vendrell, Jung Hwan Park, Young-Tae Chang

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)10077-10082
Number of pages6
JournalJournal of the American Chemical Society
Volume131
Issue number29
DOIs
Publication statusPublished - 29 Jul 2009

Keywords

  • HUMAN SERUM-ALBUMIN
  • IN-VIVO
  • SPECTROSCOPIC PROPERTIES
  • COMBINATORIAL SYNTHESIS
  • FLUORESCENT SENSORS
  • ROSAMINE LIBRARY
  • ZINC IONS
  • DYES
  • CHEMOSENSORS
  • BIOLOGY

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