Improved Synthesis of the Triazacryptand (TAC) and its Application in the Construction of a Fluorescent TAC-BODIPY Conjugate for K+ Sensing in Live Cells

In this report, a vastly improved method for the synthesis of [2.2.3]‐triazacryptand (TAC), an excellent K+‐selective cryptand, is disclosed, which provides a shorter synthetic route with > fivefold higher overall yield. On the basis of the improved synthesis, a TAC‐BODIPY conjugate was developed...

Full description

Saved in:
Bibliographic Details
Published in:European journal of organic chemistry 2015-02, Vol.2015 (6), p.1189-1192
Main Authors: Sui, Binglin, Yue, Xiling, Tichy, Michael G., Liu, Taihong, Belfield, Kevin D.
Format: Article
Language:English
Subjects:
Cell imaging
Cryptands
Fluorescence
Potassium
Sensors
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:In this report, a vastly improved method for the synthesis of [2.2.3]‐triazacryptand (TAC), an excellent K+‐selective cryptand, is disclosed, which provides a shorter synthetic route with > fivefold higher overall yield. On the basis of the improved synthesis, a TAC‐BODIPY conjugate was developed for K+ sensing. TAC‐BODIPY is a fluorescence turn‐on K+ sensor exhibiting high selectivity toward K+ over other biologically relevant metal cations. Cell imaging studies are presented and demonstrate that TAC‐BODIPY is suitable for dynamic K+ sensing in live cells. The dye, TAC‐BODIPY, emits very weak fluorescence at 512 nm. Upon binding with K+, it becomes highly fluorescent, emitting very strong fluorescence. TAC‐BODIPY exhibits excellent selectivity toward K+ over Na+ and desirable sensitivity for K+ sensing. This fluorescent K+ sensor is capable of efficiently sensing the K+ levels in living cells through cell imaging with fluorescence microscopy.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201403600