Comparison of antioxidant properties of nifedipine and illuminated nifedipine with nitroso spin traps in low density lipoproteins and phosphatidylcholine liposomes

Ondriaš, Karol; Mišı́k, Vladimı́r; Staško, Andrej; Gergeĺ, D; Hromadová, M

doi:10.1016/0005-2760(94)90145-7

Cited by 16 publications

(6 citation statements)

References 23 publications

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“…Even though low concentrations of radicals were detected, the presence of PBN led to a remarkable inhibiting effect on lipid oxidation as assessed by PV, TBA, and tocopherol depletion. These results are in agreement with the numerous reports attributing to the spin trap PBN an important role in protecting biological systems from lipid peroxidation (23)(24)(25)(26)(27)(28)(29)(30)(31). Barclay and Vinqvist (20) reported, however, that PBN does not really act as a chain-breaking antioxidant, but it acts as a weak retarder of lipid oxidation.…”

Section: Discussionsupporting

confidence: 92%

Electron Spin Resonance Spin Trapping for Analysis of Lipid Oxidation in Oils: Inhibiting Effect of the Spin Trap α-Phenyl-N-tert-butylnitrone on Lipid Oxidation

Velasco¹,

Andersen²,

Skibsted³

2005

J. Agric. Food Chem.

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The electron spin resonance (ESR) spin trapping technique was investigated as an analytical approach to follow lipid oxidation of rapeseed oil, sunflower oil, and fish oil during storage at 40 degrees C. Unlike previous investigations, alpha-phenyl-N-tert-butylnitrone (PBN), used as spin trap, was added to the fresh oils and formation of radicals was monitored during storage. Results were compared with the development in peroxide value (PV) and the thiobarbituric acid index (TBA). Increasing radical development was detected during the initial stages of oxidation, during which no significant changes in PV and TBA were observed. Evidence of spin adduct depletion was found during prolonged storage, suggesting that although spin trapping of radicals may be used to follow early events in lipid oxidation, it is not a suitable parameter for long periods of time. Addition of the spin trap after sequential samplings is recommended for getting an insight of oxidative changes during storage. Further, the influence of the spin trap (PBN) on lipid oxidation was studied in detail by application of PV and TBA and by following the depletion of naturally occurring tocopherol. PBN was found to possess a profound inhibiting effect on lipid oxidation. Such an effect was found to be dependent on the nature of the oil, and it was observed that the lower the oxidative stability, the larger the effect of PBN on lipid oxidation. This effect was interpreted in terms of the capability of PBN to react with peroxyl radicals, which in turn depends on the initial tocopherol content of the oils.

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Section: Discussionsupporting

confidence: 92%

Electron Spin Resonance Spin Trapping for Analysis of Lipid Oxidation in Oils: Inhibiting Effect of the Spin Trap α-Phenyl-N-tert-butylnitrone on Lipid Oxidation

Velasco¹,

Andersen²,

Skibsted³

2005

J. Agric. Food Chem.

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“…1,[6][7][8][9][10][11][37][38][39][40][41] However, it is not clear how nifedipine exerts these pleiotropic effects because its antioxidative activity, which is responsible for the cardiovascular protective effect, 13,14,42) is weak in comparison to other DHPs. [43][44][45][46] Incidentally, nifedipine is light-sensitive, and is converted completely to its nitroso analog, 2,6-di-methyl-4-(2-nitrosophenyl)-3,5-pyridine-carboxylic acid dimethyl ester (NO-NIF, Fig. 1) without further photochemical degradation under ordinary light in 24 h. 23) In addition, it has been reported that NO-NIF was enzymatically generated from nifedipine.…”

Section: Discussionmentioning

confidence: 99%

Antioxidant Effects of Photodegradation Product of Nifedipine

Horinouchi

Tsuchiya

Taoka

et al. 2011

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Stobadine (Figure 1), a novel drug of a pyridoindole structure, has been described to exhibit cardioprotective effects and to decrease functional damage to isolated rat hearts subjected to a period of ischemia followed by reperfusion (1,2). Experiments to detect peroxidative damage to lipids suggested that these pharmacological effects arise from antioxidant properties of stobadine (3)(4)(5)(6).…”

Section: Introductionmentioning

confidence: 99%

Antioxidant activity of the pyridoindole stobadine. Pulse radiolytic characterization of one-electron-oxidized stobadine and quenching of singlet molecular oxygen

Steenken

Sundquist²,

Jovanović³

et al. 1992

Chem. Res. Toxicol.

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Antioxidant properties of stobadine, a pyridoindole derivative described to exhibit cardioprotective properties, were characterized. The radical scavenging potential of stobadine was evaluated using pulse radiolysis with optical detection, by which it is shown that one-electron oxidation of stobadine with radicals such as C6H5O., CCl3O2., Br2.-, and HO. (reaction rate constants approximately 5 x 10(8)-10(10) M-1 s-1) leads to the radical cation (absorbance maxima at 280 and 445 nm) which deprotonates from the indolic nitrogen (pKa = 5.0) to give a nitrogen-centered radical (absorbance maxima at 275, 335, and 410 nm), probably bearing a positive charge at the pyrido nitrogen. The radical of stobadine reacts with Trolox (i.e., 6-hydroxy-2,5,7,8-tetramethyl-chromane-2-carboxylic acid) with a rate constant of 1.2 x 10(7) M-1 s-1 at pH 7.0 by one-electron oxidation to yield the phenoxyl-type radical of Trolox. This reaction is reversible (k = 2 x 10(5) M-1 s-1). The redox potential of stobadine at pH 7 is 0.58 V/NHE. Stobadine is also a quencher of singlet molecular oxygen (1O2) with an overall quenching rate constant of 1.3 x 10(8) M-1 s-1, determined with the endoperoxide of 3,3'-(1,4-naphthylene)dipropionate (NDPO2) as 1O2 source and by monitoring 1O2 photoemission with a germanium diode.

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Comparison of antioxidant properties of nifedipine and illuminated nifedipine with nitroso spin traps in low density lipoproteins and phosphatidylcholine liposomes

Cited by 16 publications

References 23 publications

Electron Spin Resonance Spin Trapping for Analysis of Lipid Oxidation in Oils: Inhibiting Effect of the Spin Trap α-Phenyl-N-tert-butylnitrone on Lipid Oxidation

Electron Spin Resonance Spin Trapping for Analysis of Lipid Oxidation in Oils: Inhibiting Effect of the Spin Trap α-Phenyl-N-tert-butylnitrone on Lipid Oxidation

Antioxidant Effects of Photodegradation Product of Nifedipine

Antioxidant activity of the pyridoindole stobadine. Pulse radiolytic characterization of one-electron-oxidized stobadine and quenching of singlet molecular oxygen

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