Interaction of carnosine with superoxide radicals in aqueous solutions

Ar, Pavlov; Ревина, А. А.; Дупин, А. М.; Aa, Boldyrev; Ai, Iaropolov

doi:10.1007/bf00842290

Cited by 6 publications

(4 citation statements)

References 5 publications

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“…The UV-Vis absorbance spectra of ruthenium-carnosine complexes were obtained in distilled water (pH 6.9) at 25 °C. Figure 3 shows the electronic absorption spectrum (nm) of 0.88 mM L -carnosine (insert), with absorbance bands observed at 264.5 ( a’ ), 214 ( b’ ), and 209 ( b’ ) which can be assigned to n-π*, π-π*, and π-π* respectively [ 24 , 25 , 36 ]. At low concentrations (0.07 mM) the peak at 265 nm of carnosine virtually disappears leaving only the broad band around 214 nm.…”

Section: Resultsmentioning

confidence: 99%

“…The amide nitrogen N9 undergoes a modest RCIS (4.2%), but this was accompanied by a larger H9 value (−6.6%). This shielding/deshielding response of different nuclei at the same position is thought to be due to conformational effects of H-bonding or interaction with OH-radicals rather than participation at the metal center [ 36 ]. Larger conformational changes in the histidine segment than in the central (amide region) of the carnosine molecule are implied during complex formation.…”

Section: Resultsmentioning

confidence: 99%

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Preparation, Spectrochemical, and Computational Analysis of L-Carnosine (2-[(3-Aminopropanoyl)amino]-3-(1H-imidazol-5-yl)propanoic Acid) and Its Ruthenium (II) Coordination Complexes in Aqueous Solution

et al. 2011

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This study reports the synthesis and characterization of novel ruthenium (II) complexes with the polydentate dipeptide, L-carnosine (2-[(3-aminopropanoyl)amino]-3-(1H-imidazol-5-yl)propanoic acid). Mixed-ligand complexes with the general composition [MLp(Cl)q(H2O)r]·xH2O (M = Ru(II); L = L-carnosine; p = 3 − q; r = 0–1; and x = 1–3) were prepared by refluxing aqueous solutions of the ligand with equimolar amounts of ruthenium chloride (black-alpha form) at 60 °C for 36 h. Physical properties of the complexes were characterized by elemental analysis, DSC/TGA, and cyclic voltammetry. The molecular structures of the complexes were elucidated using UV-Vis, ATR-IR, and heteronuclear NMR spectroscopy, then confirmed by density function theory (DFT) calculations at the B3LYP/LANL2DZ level. Two-dimensional NMR experiments (1H COSY, 13C gHMBC, and 15N gHMBC) were also conducted for the assignment of chemical shifts and calculation of relative coordination-induced shifts (RCIS) by the complex formed. According to our results, the most probable coordination geometries of ruthenium in these compounds involve nitrogen (N1) from the imidazole ring and an oxygen atom from the carboxylic acid group of the ligand as donor atoms. Additional thermogravimetric and electrochemical data suggest that while the tetrahedral-monomer or octahedral-dimer are both possible structures of the formed complexes, the metal in either structure occurs in the (2+) oxidation state. Resulting RCIS values indicate that the amide-carbonyl, and the amino-terminus of the dipeptide are not involved in chelation and these observations correlate well with theoretical shift predictions by DFT.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Preparation, Spectrochemical, and Computational Analysis of L-Carnosine (2-[(3-Aminopropanoyl)amino]-3-(1H-imidazol-5-yl)propanoic Acid) and Its Ruthenium (II) Coordination Complexes in Aqueous Solution

et al. 2011

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“…The hydroxyl radical scabengers included allopurinol (Moorehouse et ui. 1987), azelaic acid (Passi et al 1991), caffeine (Shi et al 1991), carnosine (Pavlov et al 1991;Salim-Hanna et al 1991), cimetidine (Uchida and Kawakishi 1990), dimethylsulphoxide (DMSO ; Cederbaum et al 1977;Repine et al 1981), dimethyl thiourea (Repine et al 1981) and thiourea (Cederbaum et al 1979). The hydrogen peroxide scavengers were bovine liver catalase (Martin et al 1976) and sodium pyruvate (Thompson et al 1951).…”

Section: Reactive Oxygen Intermediate Scavengersmentioning

confidence: 99%

Oxygen tolerance estimates in Campylobacter species depend on the testing medium

Hodge

Krieg

1994

Journal of Applied Bacteriology

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Oxygen tolerance of the microaerophile Campylobacter jejuni subsp. jejuni varied with different brands of complex media which were used for plating the dilute cell suspensions. The tryptone component was one factor. With some tryptones growth occurred at 21% oxygen whereas with others there was no growth at oxygen levels of 15% or higher. A chemically-defined, agar-solidified plating medium was used to estimate the oxygen tolerance of Camp. jejuni subsp. jejuni, Camp. coli and Camp. fetus subsp. fetus, and also to assess the effect of added scavengers of reactive oxygen intermediates on the oxygen tolerance. Some scavengers such as allopurinol, azelaic acid, caffeine, cimetidine, TEMPOL and pyruvate enhanced oxygen tolerance markedly whereas others such as carnosine, dimethyl thiourea, spermidine and superoxide dismutase had little effect.

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“…The amount of contaminating compound(s) is increased after boiling the alcohol-water carnosine solution in an oxygencontaining atmosphere (this does not happen in a nitrogen atmosphere). Careful anal-lysis allows us to suggest the nature of this compound and its participation in the biological action of carnosine (Pavlov et al, 1990).…”

Section: Introductionmentioning

confidence: 99%

Natural histidine-containing dipeptide Carnosine as a potent hydrophilic antioxidant with membrane stabilizing function

Boldyrev

Koldobski

Kurella

et al. 1993

Molecular and Chemical Neuropathology

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A review on the distribution and biological effects of carnosine and a hypothesis for its biological mechanisms of action are presented. Carnosine and its structural and functional relative, anserine, were found in skeletal muscles at the beginning of the century. Their effects on muscle-working capacity, on the stability of membrane-bound enzymes, as well as their potent immunomodulating property, could not be explained by their pH-buffering capacity or formation of the secondary metabolites histidine and beta-alanine alone. This article suggests that the basis for the biological activities of carnosine and relative compounds is their potent antioxidant and membrane-protecting activity. The plausible chemical mechanism of this activity is discussed, and data regarding the usage of carnosine as a drug for treatment of immunodeficiency are summarized.

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Interaction of carnosine with superoxide radicals in aqueous solutions

Cited by 6 publications

References 5 publications

Preparation, Spectrochemical, and Computational Analysis of L-Carnosine (2-[(3-Aminopropanoyl)amino]-3-(1H-imidazol-5-yl)propanoic Acid) and Its Ruthenium (II) Coordination Complexes in Aqueous Solution

Preparation, Spectrochemical, and Computational Analysis of L-Carnosine (2-[(3-Aminopropanoyl)amino]-3-(1H-imidazol-5-yl)propanoic Acid) and Its Ruthenium (II) Coordination Complexes in Aqueous Solution

Oxygen tolerance estimates in Campylobacter species depend on the testing medium

Natural histidine-containing dipeptide Carnosine as a potent hydrophilic antioxidant with membrane stabilizing function

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