Richard D Carpenter1, Alan S Verkman. 1. Departments of Medicine and Physiology, University of California, San Francisco, Health Sciences East, Room 1246, Box 0521, 513 Parnassus Ave., San Francisco, CA 94143-0521, USA ; Department of Biomedical Engineering, University of California, Davis, Genome and Biomedical Sciences Facility, 451 Health Sciences Dr., Davis, CA 95616, USA.
Abstract
Triazacryptand (TAC)-based fluorescent K+ sensors have broad biomedical utility, yet their advancement has been hindered because of their challenging synthesis. Herein, an efficient synthesis is reported that delivers a didesmethyl tri-azacryptand (ddTAC) K+ sensor in twofold fewer steps and ninefold higher overall yield than the original TAC synthesis. Our synthesis utilizes a C-O dianionic oxidative macrocyclization and reports new examples of aminoarylations and a microwave route to xanthythilium chromophores. The K+ sensitivity and selectivity of the ddTAC-based sensor are comparable to the TAC-based sensor.
Triazacryptand (n class="Chemical">TAC)-based fluorescent K+ sensors have broad biomedical utility, yet their advancement has been hindered because of their challenging synthesis. Herein, an efficient synthesis is reported that delivers a didesmethyl tri-azacryptand (ddTAC) K+ sensor in twofold fewer steps and ninefold higher overall yield than the original TAC synthesis. Our synthesis utilizes a C-O dianionic oxidative macrocyclization and reports new examples of aminoarylations and a microwave route to xanthythilium chromophores. The K+ sensitivity and selectivity of the ddTAC-based sensor are comparable to the TAC-based sensor.
Authors: Wan Namkung; Yuanlin Song; Aaron D Mills; Prashant Padmawar; Walter E Finkbeiner; A S Verkman Journal: J Biol Chem Date: 2009-04-13 Impact factor: 5.157