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Hydrophilic Reduction-Resistant Spin Labels of Pyrrolidine and Pyrroline Series from 3,4-Bis-hydroxymethyl-2,2,5,5-tetraethylpyrrolidine-1-oxyl. / Usatov, Mikhail S.; Dobrynin, Sergey A.; Polienko, Yuliya F. et al.

In: International Journal of Molecular Sciences, Vol. 25, No. 3, 1550, 02.2024.

Research output: Contribution to journalArticlepeer-review

Harvard

Usatov, MS, Dobrynin, SA, Polienko, YF, Morozov, DA, Glazachev, YI, An’kov, SV, Tolstikova, TG, Gatilov, YV, Bagryanskaya, IY, Raizvikh, AE, Bagryanskaya, EG & Kirilyuk, IA 2024, 'Hydrophilic Reduction-Resistant Spin Labels of Pyrrolidine and Pyrroline Series from 3,4-Bis-hydroxymethyl-2,2,5,5-tetraethylpyrrolidine-1-oxyl', International Journal of Molecular Sciences, vol. 25, no. 3, 1550. https://doi.org/10.3390/ijms25031550

APA

Usatov, M. S., Dobrynin, S. A., Polienko, Y. F., Morozov, D. A., Glazachev, Y. I., An’kov, S. V., Tolstikova, T. G., Gatilov, Y. V., Bagryanskaya, I. Y., Raizvikh, A. E., Bagryanskaya, E. G., & Kirilyuk, I. A. (2024). Hydrophilic Reduction-Resistant Spin Labels of Pyrrolidine and Pyrroline Series from 3,4-Bis-hydroxymethyl-2,2,5,5-tetraethylpyrrolidine-1-oxyl. International Journal of Molecular Sciences, 25(3), [1550]. https://doi.org/10.3390/ijms25031550

Vancouver

Usatov MS, Dobrynin SA, Polienko YF, Morozov DA, Glazachev YI, An’kov SV et al. Hydrophilic Reduction-Resistant Spin Labels of Pyrrolidine and Pyrroline Series from 3,4-Bis-hydroxymethyl-2,2,5,5-tetraethylpyrrolidine-1-oxyl. International Journal of Molecular Sciences. 2024 Feb;25(3):1550. doi: 10.3390/ijms25031550

Author

Usatov, Mikhail S. ; Dobrynin, Sergey A. ; Polienko, Yuliya F. et al. / Hydrophilic Reduction-Resistant Spin Labels of Pyrrolidine and Pyrroline Series from 3,4-Bis-hydroxymethyl-2,2,5,5-tetraethylpyrrolidine-1-oxyl. In: International Journal of Molecular Sciences. 2024 ; Vol. 25, No. 3.

BibTeX

@article{70d80536c6ff4245b5b4b12f4d8b7df9,
title = "Hydrophilic Reduction-Resistant Spin Labels of Pyrrolidine and Pyrroline Series from 3,4-Bis-hydroxymethyl-2,2,5,5-tetraethylpyrrolidine-1-oxyl",
abstract = "Highly resistant to reduction nitroxides open new opportunities for structural studies of biological macromolecules in their native environment inside living cells and for functional imaging of pH and thiols, enzymatic activity and redox status in living animals. 3,4-Disubstituted nitroxides of 2,2,5,5-tetraethylpyrrolidine and pyrroline series with a functional group for binding to biomolecules and a polar moiety for higher solubility in water and for more rigid attachment via additional coordination to polar sites were designed and synthesized. The EPR spectra, lipophilicities, kinetics of the reduction in ascorbate-containing systems and the decay rates in liver homogenates were measured. The EPR spectra of all 3,4-disubstituted pyrrolidine nitroxides showed additional large splitting on methylene hydrogens of the ethyl groups, while the spectra of similar pyrroline nitroxides were represented with a simple triplet with narrow lines and hyperfine structure of the nitrogen manifolds resolved in oxygen-free conditions. Both pyrrolidine and pyrroline nitroxides demonstrated low rates of reduction with ascorbate, pyrrolidines being a bit more stable than similar pyrrolines. The decay of positively charged nitroxides in the rat liver homogenate was faster than that of neutral and negatively charged radicals, with lipophilicity, rate of reduction with ascorbate and the ring type playing minor role. The EPR spectra of N,N-dimethyl-3,4-bis-(aminomethyl)-2,2,5,5-tetraethylpyrrolidine-1-oxyl showed dependence on pH with pKa = 3, ΔaN = 0.055 mT and ΔaH = 0.075 mT.",
keywords = "EPR, hyperfine coupling, reduction-resistant nitroxide, spin label, spin probe",
author = "Usatov, {Mikhail S.} and Dobrynin, {Sergey A.} and Polienko, {Yuliya F.} and Morozov, {Denis A.} and Glazachev, {Yurii I.} and An{\textquoteright}kov, {Sergey V.} and Tolstikova, {Tatiana G.} and Gatilov, {Yuri V.} and Bagryanskaya, {Irina Yu} and Raizvikh, {Arthur E.} and Bagryanskaya, {Elena G.} and Kirilyuk, {Igor A.}",
note = "This work has been supported by the grants the Russian Science Foundation, RSF 23-13-00178.",
year = "2024",
month = feb,
doi = "10.3390/ijms25031550",
language = "English",
volume = "25",
journal = "International Journal of Molecular Sciences",
issn = "1661-6596",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "3",

}

RIS

TY - JOUR

T1 - Hydrophilic Reduction-Resistant Spin Labels of Pyrrolidine and Pyrroline Series from 3,4-Bis-hydroxymethyl-2,2,5,5-tetraethylpyrrolidine-1-oxyl

AU - Usatov, Mikhail S.

AU - Dobrynin, Sergey A.

AU - Polienko, Yuliya F.

AU - Morozov, Denis A.

AU - Glazachev, Yurii I.

AU - An’kov, Sergey V.

AU - Tolstikova, Tatiana G.

AU - Gatilov, Yuri V.

AU - Bagryanskaya, Irina Yu

AU - Raizvikh, Arthur E.

AU - Bagryanskaya, Elena G.

AU - Kirilyuk, Igor A.

N1 - This work has been supported by the grants the Russian Science Foundation, RSF 23-13-00178.

PY - 2024/2

Y1 - 2024/2

N2 - Highly resistant to reduction nitroxides open new opportunities for structural studies of biological macromolecules in their native environment inside living cells and for functional imaging of pH and thiols, enzymatic activity and redox status in living animals. 3,4-Disubstituted nitroxides of 2,2,5,5-tetraethylpyrrolidine and pyrroline series with a functional group for binding to biomolecules and a polar moiety for higher solubility in water and for more rigid attachment via additional coordination to polar sites were designed and synthesized. The EPR spectra, lipophilicities, kinetics of the reduction in ascorbate-containing systems and the decay rates in liver homogenates were measured. The EPR spectra of all 3,4-disubstituted pyrrolidine nitroxides showed additional large splitting on methylene hydrogens of the ethyl groups, while the spectra of similar pyrroline nitroxides were represented with a simple triplet with narrow lines and hyperfine structure of the nitrogen manifolds resolved in oxygen-free conditions. Both pyrrolidine and pyrroline nitroxides demonstrated low rates of reduction with ascorbate, pyrrolidines being a bit more stable than similar pyrrolines. The decay of positively charged nitroxides in the rat liver homogenate was faster than that of neutral and negatively charged radicals, with lipophilicity, rate of reduction with ascorbate and the ring type playing minor role. The EPR spectra of N,N-dimethyl-3,4-bis-(aminomethyl)-2,2,5,5-tetraethylpyrrolidine-1-oxyl showed dependence on pH with pKa = 3, ΔaN = 0.055 mT and ΔaH = 0.075 mT.

AB - Highly resistant to reduction nitroxides open new opportunities for structural studies of biological macromolecules in their native environment inside living cells and for functional imaging of pH and thiols, enzymatic activity and redox status in living animals. 3,4-Disubstituted nitroxides of 2,2,5,5-tetraethylpyrrolidine and pyrroline series with a functional group for binding to biomolecules and a polar moiety for higher solubility in water and for more rigid attachment via additional coordination to polar sites were designed and synthesized. The EPR spectra, lipophilicities, kinetics of the reduction in ascorbate-containing systems and the decay rates in liver homogenates were measured. The EPR spectra of all 3,4-disubstituted pyrrolidine nitroxides showed additional large splitting on methylene hydrogens of the ethyl groups, while the spectra of similar pyrroline nitroxides were represented with a simple triplet with narrow lines and hyperfine structure of the nitrogen manifolds resolved in oxygen-free conditions. Both pyrrolidine and pyrroline nitroxides demonstrated low rates of reduction with ascorbate, pyrrolidines being a bit more stable than similar pyrrolines. The decay of positively charged nitroxides in the rat liver homogenate was faster than that of neutral and negatively charged radicals, with lipophilicity, rate of reduction with ascorbate and the ring type playing minor role. The EPR spectra of N,N-dimethyl-3,4-bis-(aminomethyl)-2,2,5,5-tetraethylpyrrolidine-1-oxyl showed dependence on pH with pKa = 3, ΔaN = 0.055 mT and ΔaH = 0.075 mT.

KW - EPR

KW - hyperfine coupling

KW - reduction-resistant nitroxide

KW - spin label

KW - spin probe

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85184677319&origin=inward&txGid=4dbc89ea373d9f9bfc61dc9804f286de

UR - https://www.webofscience.com/wos/woscc/full-record/WOS:001160339200001

UR - https://www.mendeley.com/catalogue/7c696cc5-4968-3cd6-9929-149ee6aac6cd/

U2 - 10.3390/ijms25031550

DO - 10.3390/ijms25031550

M3 - Article

C2 - 38338825

VL - 25

JO - International Journal of Molecular Sciences

JF - International Journal of Molecular Sciences

SN - 1661-6596

IS - 3

M1 - 1550

ER -

ID: 61201448