A molecular chemodosimeter to probe “closed shell” ions in kidney cells

Amine Assel; Meagan M. Stanley; Rashid Mia; Besma Boulila; Peter J. Cragg; Iyanuoluwani Owolabie; Meredith Hetrick; Alex Flynt; Karl J. Wallace; Hichem Ben Jannet

doi:10.1039/D3OB01408H

A molecular chemodosimeter to probe “closed shell” ions in kidney cells†

Amine Assel,

^a Meagan M. Stanley,^b Rashid Mia,

^bc Besma Boulila,^a Peter J. Cragg,

^d Iyanuoluwani Owolabie,

^e Meredith Hetrick,

^e Alex Flynt,

^e Karl J. Wallace

*^b and Hichem Ben Jannet

^a

Author affiliations

* Corresponding authors

^a Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity (LR11ES39), Team: Medicinal Chemistry and Natural Products, Faculty of Science of Monastir, University of Monastir, Avenue of Environment, 5019 Monastir, Tunisia

^b Department of Chemistry and Biochemistry, School of Mathematics and Natural Science, The University of Southern Mississippi, 118 College Drive, Hattiesburg, MS 39406, USA
E-mail: karl.wallace@usm.edu

^c Department of Chemistry and Biochemistry, Stephen F Austin State University, P.O. Box 13006 SFA Station, Nacogdoches, TX 75962, USA

^d School of Applied Chemical Sciences, University of Brighton, Brighton, UK

^e Department of Cellular and Molecular Biology, The University of Southern Mississippi, 118 College Drive, Hattiesburg, MS 39406, USA

Abstract

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 with 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 chemodosimter.

Organic & Biomolecular Chemistry

A molecular chemodosimeter to probe “closed shell” ions in kidney cells†

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A molecular chemodosimeter to probe “closed shell” ions in kidney cells

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