Two quinidine-functionalized coumarin molecular probes have been synthesized and have been found to bind metal cations (Cd2+, Co2+, Cu2+, Fe2+, Hg2+, Ni2+, and Zn2+) with high affinity in organic-aqueous media (DMSO-HEPES). The chemodosimeters coordinate to the Zn2+ ions in a two-to-one ratio (molecular probe:Zn2+) with a log β of 10.0 M-2. Upon the addition of the closed-shell metal ions studied, a fluorescence turn-on via an excimer formation is seen at 542 nm due to the quinaldine moiety adopting a syn arrangement when coordinated to the metal Zn2+ ions. Confocal microscopy monitored free Zn2+ ions in the Human Embryonic Kidney cell line HEK293 by coordinating with the chemodosimeter.
Bibliographical noteFunding Information:
K. J. W. would like to thank the Department of the Army US Army Engineer Research and Development Centre ERDC (Contract W912HZ-19-2-0044). A. F. would like to thank NSF award 1757220, CBET MRI 2019023 and the Mississippi INBRE P20GM103476 and H. B. J. thanks the Ministry of Higher Education and Scientific Research of Tunisia for the financial support to the LR11ES39 laboratory.
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- Organic Chemistry
- Physical and Theoretical Chemistry