Zwitterionic N2O2-Type Protonated Dipyrrin Bearing a Phosphate Anionic Moiety as a pH-Responsive Fluorescence Indicator

作者:Yamamura Masaki; Takizawa Hiroyuki; Nabeshima Tatsuya*
来源:Organic Letters, 2015, 17(12): 3114-3117.
DOI:10.1021/acs.orglett.5b01414

摘要

Zwitterionic protonated-dipyrrin 1 bearing a phosphate unit was synthesized from the N2O2-type tetradentate dipyrrin ligand. Compound 1 is in equilibrium with the deprotonated form 1' with a pK(a) value of 5.8. Compound 1 exhibited a pH-responsive fluorescence under physiological conditions; the fluorescence intensity increased in aqueous media as the pH increased. In living cells, 1 also exhibited emission responsive to pH. Thus, 1 should be applicable as a pH probe for detecting tumor cells.

  • 出版日期2015-6-19