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

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

doi:10.1039/D3OB01408H

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

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

School of Applied Sciences

Research output: Contribution to journal › Article › peer-review

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 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.

Original language	English
Pages (from-to)	9379-9391
Number of pages	13
Journal	Organic & Biomolecular Chemistry
Volume	21
Issue number	47
DOIs	https://doi.org/10.1039/D3OB01408H
Publication status	Published - 13 Nov 2023

Bibliographical note

Funding 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.

Publisher Copyright:
© 2023 The Royal Society of Chemistry

Keywords

Biochemistry
Organic Chemistry
Physical and Theoretical Chemistry

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10.1039/D3OB01408H

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title = "A molecular chemodosimeter to probe “closed shell” ions in kidney cells",

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 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. ",

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author = "Amine Assel and Meagan Stanley and Rashid Mia and Besma Boulila and Peter Cragg and Iyanuoluwani Owolabie and Meredith Hetrick and Alex Flynt and Karl Wallace and {Ben Jannet}, Hichem",

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AU - Cragg, Peter

AU - Owolabie, Iyanuoluwani

AU - Hetrick, Meredith

AU - Flynt, Alex

AU - Wallace, Karl

AU - Ben Jannet, Hichem

N1 - Funding 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. Publisher Copyright: © 2023 The Royal Society of Chemistry

PY - 2023/11/13

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N2 - 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.

AB - 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.

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KW - Physical and Theoretical Chemistry

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

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