Ozonation of methyl oleate in hexane, in a thin film, in SDS micelles, and in distearoylphosphatidylcholine liposomes: yields and properties of the Criegee ozonide

Pryor, William A.; Wu, Manhong

doi:10.1021/tx00028a008

Cited by 32 publications

(7 citation statements)

References 46 publications

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“…The CID spectrum of the [M+H] + ion of m/z 808 had product ions at m/z 184, 621, 650 and 666, which correlated to the 1,2,4-trioxolane structure (Criegee ozonide) being present at the 9-carbon at a 18-carbon chain (addition of three oxygen atoms (48 u) to PC 16:0_18:1, m/z 760) (Figure 3). The two HPLC peaks had no apparent differences in product ion spectra suggesting presence of cis and trans structures as observed previously [27]. …”

Section: Resultssupporting

confidence: 74%

Identification of oxidized phospholipids in bronchoalveolar lavage exposed to low ozone levels using multivariate analysis

Almstrand

Voelker

Murphy

2015

Analytical Biochemistry

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Chemical reactions with unsaturated phospholipids in the respiratory tract lining fluid have been identified as one of the first important steps in the mechanisms mediating environmental ozone toxicity. As a consequence of these reactions, complex mixtures of oxidized lipids are generated in the presence of mixtures of non-oxidized naturally occurring phospholipid molecular species, which challenge methods of analysis. Untargeted mass spectrometry and statistical methods were employed to approach these complex spectra. Human bronchoalveolar lavage (BAL) was exposed to low levels of ozone and samples, with and without derivatization of aldehydes, were analyzed by liquid chromatography electrospray ionization tandem mass spectrometry. Data processing was carried out using principal component analysis (PCA). Resulting PCA score plots indicated an ozone dose-dependent increase, with apparent separation between BAL samples exposed to 60 ppb ozone and non-exposed BAL samples, and a clear separation between ozonized samples before and after derivatization. Corresponding loadings plots revealed that more than 30 phosphatidylcholine (PC) species decreased due to ozonation. A total of 13 PC and 6 phosphatidylglycerol oxidation products were identified with the majority being structurally characterized as chain-shortened aldehyde products. This method exemplifies an approach for comprehensive detection of low abundance, yet important, components in complex lipid samples.

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Section: Resultssupporting

confidence: 74%

Identification of oxidized phospholipids in bronchoalveolar lavage exposed to low ozone levels using multivariate analysis

Almstrand

Voelker

Murphy

2015

Analytical Biochemistry

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“…The fact that SOZ is still observable at 1.4 Â 10 17 molecules H 2 O cm À3 (20% RH) shows that the CI is not completely trapped by water, and some CI can still recombine with the aldehyde. Similar observations were made for the ozonolysis of POPC liposomes in aqueous solution 94 and methyl oleate in aqueous micelles of sodium dodecyl sulfate 95 where the yields of SOZ were 11%, compared to 89% for the methyl oleate reaction in hexane. SOZ production was also observed in the reaction of O 3 with 1-palmitoyl-2-oleoyl-sn-phosphatidylglycerol surfactant on a 1 : 1 water-methanol solution.…”

Section: Kineticssupporting

confidence: 75%

“…94 and methyl oleate in aqueous micelles of sodium dodecyl sulfate 95 where the yields of SOZ were 11%, compared to 89% for the methyl oleate reaction in hexane. SOZ production was also observed in the reaction of O 3 with 1-palmitoyl-2-oleoyl-sn-phosphatidylglycerol surfactant on a 1 : 1 water-methanol solution.…”

Section: Kineticsmentioning

confidence: 95%

Heterogeneous oxidation of a phosphocholine on synthetic sea salt by ozone at room temperature

Dilbeck

Finlayson-Pitts

2013

Phys. Chem. Chem. Phys.

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The ozonolysis of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) adsorbed on salt mixtures as models for sea-salt particles was studied in real time using diffuse reflection infrared Fourier transform spectrometry (DRIFTS) at room temperature with and without added water vapor. The salt substrates were a mixture of MgCl 2 Á6H 2 O with NaCl or a commercially available synthetic sea salt. Ozone concentrations ranged from (0.25 to 3.9) Â 10 13 molecules cm À3 (0.1-1.6 ppm). The major products identified by FTIR and confirmed using matrix-assisted laser desorption/ionization (MALDI) mass spectrometry were the secondary ozonide (SOZ) and a phospholipid aldehyde and carboxylic acid formed by scission of the double bond. The reaction probabilities for the two substrates were similar, g = (6-7) Â 10 À7 , with an estimated overall uncertainty of a factor of two. The presence of water vapor decreased the yield of SOZ relative to the products formed by CQC scission, but also increased the availability of the double bond for reaction, particularly on the less hygroscopic commercial sea-salt substrate. Thus, water not only affects the mechanisms and products, but also the structure of the phospholipid on the salt in a manner that affects its reactivity. The results of these studies suggest that the reactivity and products of oxidation of unsaturated phospholipids on sea-salt particles in air will be very sensitive to the nature and phase of the substrate, the amount of water present, and whether there is phase separation between the organics and the inorganic salt mixture.

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“…Only a small number of studies have investigated the effectiveness of ozone therapy on periodontal parameters. The approach was expected to significantly improve the glycated hemoglobin (HbA1C) level [ 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 ]. Our results showed that both treatments resulted in significant improvements in all clinical and biochemical parameters, showing no significant difference between the conventional periodontal treatment and the treatment with a conjunction of gaseous ozone after 12 months.…”

Section: Discussionmentioning

confidence: 99%

The Effect of Gaseous Ozone Therapy in Conjunction with Periodontal Treatment on Glycated Hemoglobin Level in Subjects with Type 2 Diabetes Mellitus: An Unmasked Randomized Controlled Trial

Rapone

Ferrara

Corsalini

et al. 2020

IJERPH

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Background: It is established that inflammation is involved in the pathogenesis of Type 2 Diabetes Mellitus (T2DM) by promoting insulin resistance and impaired beta cell function in the pancreas. Among the hypothesized independent risk factors implicated in the pathogenetic basis of disease, periodontal infection has been proposed to promote an amplification of the magnitude of the advanced glycation end product (AGE)-mediated upregulation of cytokine synthesis and secretion. These findings suggest an interrelationship between periodontal disease and type 2 diabetes, describing poor metabolic control in subjects with periodontitis as compared to nondiabetic subjects and more severe periodontitis in subjects with T2DM as compared to a healthy population, with a significant positive correlation between periodontal inflammatory parameters and glycated hemoglobin level. Results from clinical trials show that periodontal treatment is able to improve glycemic control in subjects with diabetes. Many therapeutic strategies have been developed to improve periodontal conditions in conjunction with conventional treatment, among which ozone (O3) is of specific concern. The principal aim of this trial was to compare the clinical effectiveness of an intensive periodontal intervention consisting of conventional periodontal treatment in conjunction with ozone gas therapy in reducing glycated hemoglobin level in type 2 diabetic patients and standard periodontal treatment. Methods: This study was a 12-month unmasked randomized trial and included 100 patients aged 40–74 years older, with type 2 diabetes mellitus diagnosed. All the patients received conventional periodontal treatment, or periodontal treatment in conjunction with ozone gas therapy in a randomly assigned order (1:1). The primary outcome was a clinical measure of glycated hemoglobin level at 3, 6, 9 and 12 months from randomization. Secondary outcomes were changes in periodontal inflammatory parameters. Results: At 12 months, the periodontal treatment in conjunction with ozone gas therapy did not show significant differences than standard therapy in decreasing glycated hemoglobin (HbA1C) level and the lack of significant differences in balance is evident. Conclusions: Although the change was not significant, periodontal treatment in conjunction with the gaseous ozone therapy tended to reduce the levels of glycated hemoglobin. The study shows a benefit with ozone therapy as compared to traditional periodontal treatment.

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Ozonation of methyl oleate in hexane, in a thin film, in SDS micelles, and in distearoylphosphatidylcholine liposomes: yields and properties of the Criegee ozonide

Cited by 32 publications

References 46 publications

Identification of oxidized phospholipids in bronchoalveolar lavage exposed to low ozone levels using multivariate analysis

Identification of oxidized phospholipids in bronchoalveolar lavage exposed to low ozone levels using multivariate analysis

Heterogeneous oxidation of a phosphocholine on synthetic sea salt by ozone at room temperature

The Effect of Gaseous Ozone Therapy in Conjunction with Periodontal Treatment on Glycated Hemoglobin Level in Subjects with Type 2 Diabetes Mellitus: An Unmasked Randomized Controlled Trial

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