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Review
. 2024 Jan 24;25(3):1446.
doi: 10.3390/ijms25031446.

The Cellular and Organismal Effects of Nitroxides and Nitroxide-Containing Nanoparticles

Izabela Sadowska-Bartosz  1 , Grzegorz Bartosz  1
Affiliations
Review

The Cellular and Organismal Effects of Nitroxides and Nitroxide-Containing Nanoparticles

Izabela Sadowska-Bartosz et al. Int J Mol Sci. .

Abstract

Nitroxides are stable free radicals that have antioxidant properties. They react with many types of radicals, including alkyl and peroxyl radicals. They act as mimics of superoxide dismutase and stimulate the catalase activity of hemoproteins. In some situations, they may exhibit pro-oxidant activity, mainly due to the formation of oxoammonium cations as products of their oxidation. In this review, the cellular effects of nitroxides and their effects in animal experiments and clinical trials are discussed, including the beneficial effects in various pathological situations involving oxidative stress, protective effects against UV and ionizing radiation, and prolongation of the life span of cancer-prone mice. Nitroxides were used as active components of various types of nanoparticles. The application of these nanoparticles in cellular and animal experiments is also discussed.

Keywords: TEMPAMINE; TEMPO; TEMPOL; nitroxides; redox nanoparticles.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structures of various nitroxides. 1: 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO); 2: 4-hydroxy-TEMPO (TEMPOL); 3: 4-amino-TEMPO (TEMPAMINE); 4: TEMPONE; 5: 4-methoxy-TEMPO; 6: 4-acetamido-TEMPO; 7: TEMP: TEMP2, R = CH3CH2; TEMP8, R = (CH2)7CH3; 8: TINO; 9: TEEPONE; 10: 3-carboxy-PROXYL (3-CP); 11: 4-amino-2,2,5,5-tetramethyl-3-imidazoline-1-oxyl (ATI); 12: 3-carbamoyl-proxyl (3-CP); 13: 2,2,5,5-tetramethyl-4-nitromethylene-3-imidazolidine-N-oxyl (NTI); 14: 3,4-dimethyl-2,2,5,5-tetraethylperhydroimidazol-1-oxyl); 15: 4-methyl-2,2,5,5-tetraethyl-2,5-dihydro-1H-imidazol-1-oxyl; 16: OXANO; 17: CHD; 18: 1,2-dihydro-2-methyl-2-phenyl-3H-indole-3-phenylimino-1-oxyl (X = NPh or = CH2CH3); 19: L-N-p-nitrobenzoylpyrrolidinyl(4,5-dihydro-4,4,5,5-tetramethyl-3-oxido-1H-imidazol-3-ium-1-oxyl-2-yl) (L-NNNBP); 20: (2,4-dimetoxyphenyl)-4,4,5,5-tetra-methylimidazoline-1-oxyl-3-oxide (NNR); 21: NNR-arginine conjugate; 22: OT-551; 23: 2-(2,2,6,6-tetramethylpiperidin-1-oxyl-4-ylamino)-2-oxoethyl)triphenylphosphonium (Mito-TEMPO); 24: 5-doxylstearic acid; 25: 16-doxylstearic acid; 26: lecithin labeled with 12-doxylstearic acid; 27: 3-doxylcholestane.
Figure 1
Figure 1
Structures of various nitroxides. 1: 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO); 2: 4-hydroxy-TEMPO (TEMPOL); 3: 4-amino-TEMPO (TEMPAMINE); 4: TEMPONE; 5: 4-methoxy-TEMPO; 6: 4-acetamido-TEMPO; 7: TEMP: TEMP2, R = CH3CH2; TEMP8, R = (CH2)7CH3; 8: TINO; 9: TEEPONE; 10: 3-carboxy-PROXYL (3-CP); 11: 4-amino-2,2,5,5-tetramethyl-3-imidazoline-1-oxyl (ATI); 12: 3-carbamoyl-proxyl (3-CP); 13: 2,2,5,5-tetramethyl-4-nitromethylene-3-imidazolidine-N-oxyl (NTI); 14: 3,4-dimethyl-2,2,5,5-tetraethylperhydroimidazol-1-oxyl); 15: 4-methyl-2,2,5,5-tetraethyl-2,5-dihydro-1H-imidazol-1-oxyl; 16: OXANO; 17: CHD; 18: 1,2-dihydro-2-methyl-2-phenyl-3H-indole-3-phenylimino-1-oxyl (X = NPh or = CH2CH3); 19: L-N-p-nitrobenzoylpyrrolidinyl(4,5-dihydro-4,4,5,5-tetramethyl-3-oxido-1H-imidazol-3-ium-1-oxyl-2-yl) (L-NNNBP); 20: (2,4-dimetoxyphenyl)-4,4,5,5-tetra-methylimidazoline-1-oxyl-3-oxide (NNR); 21: NNR-arginine conjugate; 22: OT-551; 23: 2-(2,2,6,6-tetramethylpiperidin-1-oxyl-4-ylamino)-2-oxoethyl)triphenylphosphonium (Mito-TEMPO); 24: 5-doxylstearic acid; 25: 16-doxylstearic acid; 26: lecithin labeled with 12-doxylstearic acid; 27: 3-doxylcholestane.
Figure 1
Figure 1
Structures of various nitroxides. 1: 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO); 2: 4-hydroxy-TEMPO (TEMPOL); 3: 4-amino-TEMPO (TEMPAMINE); 4: TEMPONE; 5: 4-methoxy-TEMPO; 6: 4-acetamido-TEMPO; 7: TEMP: TEMP2, R = CH3CH2; TEMP8, R = (CH2)7CH3; 8: TINO; 9: TEEPONE; 10: 3-carboxy-PROXYL (3-CP); 11: 4-amino-2,2,5,5-tetramethyl-3-imidazoline-1-oxyl (ATI); 12: 3-carbamoyl-proxyl (3-CP); 13: 2,2,5,5-tetramethyl-4-nitromethylene-3-imidazolidine-N-oxyl (NTI); 14: 3,4-dimethyl-2,2,5,5-tetraethylperhydroimidazol-1-oxyl); 15: 4-methyl-2,2,5,5-tetraethyl-2,5-dihydro-1H-imidazol-1-oxyl; 16: OXANO; 17: CHD; 18: 1,2-dihydro-2-methyl-2-phenyl-3H-indole-3-phenylimino-1-oxyl (X = NPh or = CH2CH3); 19: L-N-p-nitrobenzoylpyrrolidinyl(4,5-dihydro-4,4,5,5-tetramethyl-3-oxido-1H-imidazol-3-ium-1-oxyl-2-yl) (L-NNNBP); 20: (2,4-dimetoxyphenyl)-4,4,5,5-tetra-methylimidazoline-1-oxyl-3-oxide (NNR); 21: NNR-arginine conjugate; 22: OT-551; 23: 2-(2,2,6,6-tetramethylpiperidin-1-oxyl-4-ylamino)-2-oxoethyl)triphenylphosphonium (Mito-TEMPO); 24: 5-doxylstearic acid; 25: 16-doxylstearic acid; 26: lecithin labeled with 12-doxylstearic acid; 27: 3-doxylcholestane.
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