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Redox Transformations of the OX063 Radical in Biological Media: Oxidative Decay of Initial Trityl with Further Formation of Structurally‐Modified TAM. / Ovcherenko, Sergey S.; Raizvich, Arthur E.; Rogozhnikova, Olga Yu. et al.

In: Chemistry - A European Journal, Vol. 30, No. 52, e202400718, 16.09.2024.

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

Harvard

Ovcherenko, SS, Raizvich, AE, Rogozhnikova, OY, Tormyshev, VM, Trukhin, DV, Koval, VV, Salnikov, GE, Genaev, AM, Shernyukov, AV & Bagryanskaya, EG 2024, 'Redox Transformations of the OX063 Radical in Biological Media: Oxidative Decay of Initial Trityl with Further Formation of Structurally‐Modified TAM', Chemistry - A European Journal, vol. 30, no. 52, e202400718. https://doi.org/10.1002/chem.202400718

APA

Ovcherenko, S. S., Raizvich, A. E., Rogozhnikova, O. Y., Tormyshev, V. M., Trukhin, D. V., Koval, V. V., Salnikov, G. E., Genaev, A. M., Shernyukov, A. V., & Bagryanskaya, E. G. (2024). Redox Transformations of the OX063 Radical in Biological Media: Oxidative Decay of Initial Trityl with Further Formation of Structurally‐Modified TAM. Chemistry - A European Journal, 30(52), [e202400718]. https://doi.org/10.1002/chem.202400718

Vancouver

Ovcherenko SS, Raizvich AE, Rogozhnikova OY, Tormyshev VM, Trukhin DV, Koval VV et al. Redox Transformations of the OX063 Radical in Biological Media: Oxidative Decay of Initial Trityl with Further Formation of Structurally‐Modified TAM. Chemistry - A European Journal. 2024 Sept 16;30(52):e202400718. doi: 10.1002/chem.202400718

Author

Ovcherenko, Sergey S. ; Raizvich, Arthur E. ; Rogozhnikova, Olga Yu. et al. / Redox Transformations of the OX063 Radical in Biological Media: Oxidative Decay of Initial Trityl with Further Formation of Structurally‐Modified TAM. In: Chemistry - A European Journal. 2024 ; Vol. 30, No. 52.

BibTeX

@article{258cfbca46ff4181b0dddfc0d93c4c13,
title = "Redox Transformations of the OX063 Radical in Biological Media: Oxidative Decay of Initial Trityl with Further Formation of Structurally‐Modified TAM",
abstract = "Being a low-toxic and hydrophilic representative of TAM, OX063 has shown its suitability for in-vivo and in-cell EPR experiments and design of spin labels. Using 13C labeling, we investigated the course of oxidative degradation of OX063 into quinone-methide (QM) under the influence of superoxide as well as further thiol-promoted reduction of QM into TAM radical, which formally corresponds to substitution of a carboxyl function by a hydroxyl group. We found these transformations being quantitative in model reactions mimicking specific features of biological media and confirmed the presence of these reactions in the blood and liver homogenate of mice in vitro. The emergence of the trityl with the hydroxyl group can be masked by an initial TAM in EPR spectra and may introduce distortions into EPR-derived oximetry data if they have been obtained for objects under hypoxia. 13C labeling allows one to detect its presence, considering its different hyperfine splitting constant on 13C1 (2.04 mT) as compared to OX063 (2.30 mT). The potential involvement of these reactions should be considered when using TAM in spin-labeling of biopolymers intended for subsequent EPR experiments, as well as in the successful application of TAM in experiments in vivo and in cell. ",
keywords = "Oxidation-Reduction, Animals, Mice, Electron Spin Resonance Spectroscopy, Triphenylmethyl Compounds/chemistry, Spin Labels, Carbon Isotopes/chemistry, Free Radicals/chemistry, Liver/metabolism",
author = "Ovcherenko, {Sergey S.} and Raizvich, {Arthur E.} and Rogozhnikova, {Olga Yu.} and Tormyshev, {Victor M.} and Trukhin, {Dmitry V.} and Koval, {Vladimir V.} and Salnikov, {Georgii E.} and Genaev, {Alexander M.} and Shernyukov, {Andrey V.} and Bagryanskaya, {Elena G.}",
note = "This work was supported by grants from the Russian ScienceFoundation (RSF 24-23-00454, to A.E.R., O.Y.R., and V.M.T.; RSF 21-14-00219, to S.S.O. and E.G.B.). We thank Dr. S.V. An{\textquoteright}kov forproviding and preparing the samples of blood and liverhomogenates of mice. We thank the personnel of the Multi-Access Center of SB RAS for recording the IR, UV, NMR, andHRMS spectra and for the elemental analyses.",
year = "2024",
month = sep,
day = "16",
doi = "10.1002/chem.202400718",
language = "English",
volume = "30",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "52",

}

RIS

TY - JOUR

T1 - Redox Transformations of the OX063 Radical in Biological Media: Oxidative Decay of Initial Trityl with Further Formation of Structurally‐Modified TAM

AU - Ovcherenko, Sergey S.

AU - Raizvich, Arthur E.

AU - Rogozhnikova, Olga Yu.

AU - Tormyshev, Victor M.

AU - Trukhin, Dmitry V.

AU - Koval, Vladimir V.

AU - Salnikov, Georgii E.

AU - Genaev, Alexander M.

AU - Shernyukov, Andrey V.

AU - Bagryanskaya, Elena G.

N1 - This work was supported by grants from the Russian ScienceFoundation (RSF 24-23-00454, to A.E.R., O.Y.R., and V.M.T.; RSF 21-14-00219, to S.S.O. and E.G.B.). We thank Dr. S.V. An’kov forproviding and preparing the samples of blood and liverhomogenates of mice. We thank the personnel of the Multi-Access Center of SB RAS for recording the IR, UV, NMR, andHRMS spectra and for the elemental analyses.

PY - 2024/9/16

Y1 - 2024/9/16

N2 - Being a low-toxic and hydrophilic representative of TAM, OX063 has shown its suitability for in-vivo and in-cell EPR experiments and design of spin labels. Using 13C labeling, we investigated the course of oxidative degradation of OX063 into quinone-methide (QM) under the influence of superoxide as well as further thiol-promoted reduction of QM into TAM radical, which formally corresponds to substitution of a carboxyl function by a hydroxyl group. We found these transformations being quantitative in model reactions mimicking specific features of biological media and confirmed the presence of these reactions in the blood and liver homogenate of mice in vitro. The emergence of the trityl with the hydroxyl group can be masked by an initial TAM in EPR spectra and may introduce distortions into EPR-derived oximetry data if they have been obtained for objects under hypoxia. 13C labeling allows one to detect its presence, considering its different hyperfine splitting constant on 13C1 (2.04 mT) as compared to OX063 (2.30 mT). The potential involvement of these reactions should be considered when using TAM in spin-labeling of biopolymers intended for subsequent EPR experiments, as well as in the successful application of TAM in experiments in vivo and in cell.

AB - Being a low-toxic and hydrophilic representative of TAM, OX063 has shown its suitability for in-vivo and in-cell EPR experiments and design of spin labels. Using 13C labeling, we investigated the course of oxidative degradation of OX063 into quinone-methide (QM) under the influence of superoxide as well as further thiol-promoted reduction of QM into TAM radical, which formally corresponds to substitution of a carboxyl function by a hydroxyl group. We found these transformations being quantitative in model reactions mimicking specific features of biological media and confirmed the presence of these reactions in the blood and liver homogenate of mice in vitro. The emergence of the trityl with the hydroxyl group can be masked by an initial TAM in EPR spectra and may introduce distortions into EPR-derived oximetry data if they have been obtained for objects under hypoxia. 13C labeling allows one to detect its presence, considering its different hyperfine splitting constant on 13C1 (2.04 mT) as compared to OX063 (2.30 mT). The potential involvement of these reactions should be considered when using TAM in spin-labeling of biopolymers intended for subsequent EPR experiments, as well as in the successful application of TAM in experiments in vivo and in cell.

KW - Oxidation-Reduction

KW - Animals

KW - Mice

KW - Electron Spin Resonance Spectroscopy

KW - Triphenylmethyl Compounds/chemistry

KW - Spin Labels

KW - Carbon Isotopes/chemistry

KW - Free Radicals/chemistry

KW - Liver/metabolism

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85205342299&origin=inward&txGid=3b608cc0901cd0e78949718bceb926e9

UR - https://www.elibrary.ru/item.asp?id=68837841

UR - https://www.mendeley.com/catalogue/151da4dd-c465-3682-9a41-36a08864ea1d/

U2 - 10.1002/chem.202400718

DO - 10.1002/chem.202400718

M3 - Article

C2 - 39003595

VL - 30

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 52

M1 - e202400718

ER -

ID: 60814151