Discriminative Detection of Biothiols by Electron Paramagnetic Resonance Spectroscopy using a Methanethiosulfonate Trityl Probe

Tan, Xiaoli; Ji, Kaiyun; Wang, Xing; Yao, Ru; Han, Guifang; Villamena, Frederick A.; Zweíer, Jay L.; Song, Yuguang; Rockenbauer, Antal; Liu, Yangping

doi:10.1002/ange.201912832

Cited by 9 publications

(4 citation statements)

References 56 publications

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“…Initially, trityl radicals with a single narrow EPR line and high stability in living subjects were proposed as advanced oximetric probes [ 22 , 46 , 47 ] for in vivo tissue oxygen mapping. In the last decade, the trityl probes and labels with extended functional sensitivity [ 48 , 49 , 50 , 51 , 52 , 53 ] were synthesized. Multifunctional trityl probes were used for in vivo concurrent spectroscopy and imaging of tissue p O 2 , pH and interstitial inorganic phosphate, Pi [ 28 , 29 ].…”

Section: Discussionmentioning

confidence: 99%

Biological Applications of Electron Paramagnetic Resonance Viscometry Using a 13C-Labeled Trityl Spin Probe

et al. 2021

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Alterations in viscosity of biological fluids and tissues play an important role in health and diseases. It has been demonstrated that the electron paramagnetic resonance (EPR) spectrum of a 13C-labeled trityl spin probe (13C-dFT) is highly sensitive to the local viscosity of its microenvironment. In the present study, we demonstrate that X-band (9.5 GHz) EPR viscometry using 13C-dFT provides a simple tool to accurately measure the microviscosity of human blood in microliter volumes obtained from healthy volunteers. An application of low-field L-band (1.2 GHz) EPR with a penetration depth of 1–2 cm allowed for microviscosity measurements using 13C-dFT in the living tissues from isolated organs and in vivo in anesthetized mice. In summary, this study demonstrates that EPR viscometry using a 13C-dFT probe can be used to noninvasively and rapidly measure the microviscosity of blood and interstitial fluids in living tissues and potentially to evaluate this biophysical marker of microenvironment under various physiological and pathological conditions in preclinical and clinical settings.

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Section: Discussionmentioning

confidence: 99%

Biological Applications of Electron Paramagnetic Resonance Viscometry Using a 13C-Labeled Trityl Spin Probe

et al. 2021

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“…Composed of glutamic acid, cysteine, and glycine, GSH possesses remarkable antioxidative properties, safeguarding the sulfhydryl groups in proteins and enzymes, thereby preserving their redox state. , With varying concentrations ranging from 0.5 to 15 mM depending on cell type, GSH levels exhibit significant differences between healthy and cancerous tissues . Aberrant GSH concentrations have been linked to a spectrum of ailments, including liver damage, Alzheimer’s, Parkinson’s, coronary heart disease, edema, slowed growth, clinical stroke, lung damage, and asthma. , The critical role of GSH in maintaining physiological homeostasis underscores the need for sensitive and selective detection methods. , Among these approaches, fluorescence-based sensing methods utilizing small molecule probes have emerged as frontrunners due to their simplicity, noninvasive nature, high sensitivity, and excellent reproducibility in biological settings. − Moreover, copper and GSH have a strong interaction within water. The GSH, a vital biological molecule, can be affected by copper through oxidation.…”

Section: Introductionmentioning

confidence: 99%

“… 27 , 28 Among these approaches, fluorescence-based sensing methods utilizing small molecule probes have emerged as frontrunners due to their simplicity, noninvasive nature, high sensitivity, and excellent reproducibility in biological settings. 29 − 31 Moreover, copper and GSH have a strong interaction within water. The GSH, a vital biological molecule, can be affected by copper through oxidation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Phenol-Hydrazide-Appended Tetraphenylethenes as Novel On–Off–On Cascade Sensors of Copper and Glutathione

Bayindir,

Akar

2024

ACS Omega

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This study reports the synthesis of novel fluorescent probes, phenol-hydrazide-appended tetraphenylethenes (TPEs I and II), and explores their photochemical properties. The probes exhibit aggregation-induced emission (AIE) in increasing water content, as observed using fluorescence spectroscopy. Further investigation with UV−vis and fluorescence techniques revealed their potential as ion sensors. Both TPE I and TPE II act as "turnoff" sensors for Cu 2+ ions, showing decreased fluorescence intensity in their presence. Their limit of detection (LOD) and association constant (K a ) for Cu 2+ were found to be comparable at 747 nM/597 nM, and 2.46 × 10 5 M −1/2 /1.78 × 10 5 M −1/2 , respectively. Moreover, the quantum yields of TPE I and TPE II were also calculated and found to be 0.651 and 0.325, respectively. Interestingly, these probes also function as "turn-on" sensors for glutathione (GSH) in the presence of copper. This means their fluorescence can be reversibly switched off and on by alternating CuCl 2 and GSH additions. Moreover, the LOD values for GSH with TPE II−Cu 2+ were calculated to be 544 nM. In addition, the investigation also employed visual analysis to assess the color alterations of TPEs on filter paper and in real water samples. Overall, this research introduces promising new probes with potential applications in copper ion detection and biomolecule glutathione sensing in real water samples.

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“…One of the simplest entities showing propensity to residual stereoisomerism, namely, the triphenylmethyl group (CPh 3 , Tr, trityl), is currently used in organic synthesis as protecting devices, catalysts, 4 , 5 construction of molecular machines, 6 medical chemistry, 7 and bioimaging. 8 …”

Section: Introductionmentioning

confidence: 99%

Chiral Triphenylacetic Acid Esters: Residual Stereoisomerism and Solid-State Variability of Molecular Architectures

2021

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We have proven the usability and versatility of chiral triphenylacetic acid esters, compounds of high structural diversity, as chirality-sensing stereodynamic probes and as molecular tectons in crystal engineering. The low energy barrier to stereoisomer interconversion has been exploited to sense the chirality of an alkyl substituent in the esters. The structural information are cascaded from the permanently chiral alcohol (inducer) to the stereodynamic chromophoric probe through cooperative interactions. The ECD spectra of triphenylacetic acid esters are highly sensitive to very small structural differences in the inducer core. The tendencies to maximize the C–H···O hydrogen bonds, van der Waals interactions, and London dispersion forces determine the way of packing molecules in the crystal lattice. The phenyl embraces of trityl groups allowed, to some extent, the control of molecular organization in the crystal. However, the spectrum of possible molecular arrangements is very broad and depends on the type of substituent, the optical purity of the sample, and the presence of a second trityl group in the proximity. Racemates crystallize as the solid solution of enantiomers, where the trityl group acts as a protecting group for the stereogenic center. Therefore, the absolute configuration of the inducer is irrelevant to the packing mode of molecules in the crystal.

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Discriminative Detection of Biothiols by Electron Paramagnetic Resonance Spectroscopy using a Methanethiosulfonate Trityl Probe

Cited by 9 publications

References 56 publications

Biological Applications of Electron Paramagnetic Resonance Viscometry Using a 13C-Labeled Trityl Spin Probe

Biological Applications of Electron Paramagnetic Resonance Viscometry Using a 13C-Labeled Trityl Spin Probe

Synthesis of Phenol-Hydrazide-Appended Tetraphenylethenes as Novel On–Off–On Cascade Sensors of Copper and Glutathione

Chiral Triphenylacetic Acid Esters: Residual Stereoisomerism and Solid-State Variability of Molecular Architectures

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