Copper(ii) complexes for cysteine detection using 19F magnetic resonance

José S. Enriquez; Meng Yu; Bailey S. Bouley; Da Xie; Emily L. Que

doi:10.1039/c8dt03780a

Copper(ii) complexes for cysteine detection using ¹⁹F magnetic resonance

José S. Enriquez, Meng Yu, Bailey S. Bouley, Da Xie, Emily L. Que^*

^*Corresponding author for this work

Department of Chemistry, University of Texas at Austin

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

27 Citations (Scopus)

Abstract

Cysteine plays an essential role in maintaining cellular redox homeostasis and perturbations in cysteine concentration are associated with cardiovascular disease, liver disease, and cancer. ¹⁹F MRI is a promising modality for detecting cysteine in biology due to its high tissue penetration and negligible biological background signal. Herein we report fluorinated macrocyclic copper complexes that display a ¹⁹F NMR/MRI turn-on response following reduction of the Cu(ii) complexes by cysteine. The reactivity with cysteine was studied by monitoring the appearance of a robust diamagnetic ¹⁹F signal following addition of cysteine in conjunction with UV-vis and EPR spectroscopies. Importantly, complexes with-CH₂CF₃ tags display good water solubility. Studies with this complex in HeLa cells demonstrate the applicability of these probes to detect cysteine in complex biological environments.

Original language	English
Pages (from-to)	15024-15030
Number of pages	7
Journal	Dalton Transactions
Volume	47
Issue number	42
DOIs	https://doi.org/10.1039/c8dt03780a
Publication status	Published - 2018
Externally published	Yes

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abstract = "Cysteine plays an essential role in maintaining cellular redox homeostasis and perturbations in cysteine concentration are associated with cardiovascular disease, liver disease, and cancer. 19F MRI is a promising modality for detecting cysteine in biology due to its high tissue penetration and negligible biological background signal. Herein we report fluorinated macrocyclic copper complexes that display a 19F NMR/MRI turn-on response following reduction of the Cu(ii) complexes by cysteine. The reactivity with cysteine was studied by monitoring the appearance of a robust diamagnetic 19F signal following addition of cysteine in conjunction with UV-vis and EPR spectroscopies. Importantly, complexes with-CH2CF3 tags display good water solubility. Studies with this complex in HeLa cells demonstrate the applicability of these probes to detect cysteine in complex biological environments.",

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T1 - Copper(ii) complexes for cysteine detection using 19F magnetic resonance

AU - Enriquez, José S.

AU - Yu, Meng

AU - Bouley, Bailey S.

AU - Xie, Da

AU - Que, Emily L.

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

PY - 2018

Y1 - 2018

N2 - Cysteine plays an essential role in maintaining cellular redox homeostasis and perturbations in cysteine concentration are associated with cardiovascular disease, liver disease, and cancer. 19F MRI is a promising modality for detecting cysteine in biology due to its high tissue penetration and negligible biological background signal. Herein we report fluorinated macrocyclic copper complexes that display a 19F NMR/MRI turn-on response following reduction of the Cu(ii) complexes by cysteine. The reactivity with cysteine was studied by monitoring the appearance of a robust diamagnetic 19F signal following addition of cysteine in conjunction with UV-vis and EPR spectroscopies. Importantly, complexes with-CH2CF3 tags display good water solubility. Studies with this complex in HeLa cells demonstrate the applicability of these probes to detect cysteine in complex biological environments.

AB - Cysteine plays an essential role in maintaining cellular redox homeostasis and perturbations in cysteine concentration are associated with cardiovascular disease, liver disease, and cancer. 19F MRI is a promising modality for detecting cysteine in biology due to its high tissue penetration and negligible biological background signal. Herein we report fluorinated macrocyclic copper complexes that display a 19F NMR/MRI turn-on response following reduction of the Cu(ii) complexes by cysteine. The reactivity with cysteine was studied by monitoring the appearance of a robust diamagnetic 19F signal following addition of cysteine in conjunction with UV-vis and EPR spectroscopies. Importantly, complexes with-CH2CF3 tags display good water solubility. Studies with this complex in HeLa cells demonstrate the applicability of these probes to detect cysteine in complex biological environments.

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JO - Dalton Transactions

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Copper(ii) complexes for cysteine detection using ¹⁹F magnetic resonance

Abstract

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