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Reactions of dinitrogen pentoxide and nitrogen dioxide with 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine

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Lipids

Abstract

The reactions of gaseous dinitrogen pentoxide (N2O5) and nitrogen dioxide (NO2) with 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) coated on the inside surface of a glass reaction cell were studied at 298 K. Unsaturated phosphatidylcholines are significant components of pulmonary surfactant in the alveolar region of the lung and hence serve as a simple model to examine reactions of pulmonary surfactant with these oxidant air pollutants. Using high-performance liquid chromatography (HPLC), Fourier transform infrared and fast atom bombardment mass spectroscopy, the major products of reactions of POPC with N2O5 and NO2 were separated and identified. In the POPC-N2O5 reaction using either air or helium as a buffer gas, the nitronitrate, vinyl nitro and allylic nitro derivatives, as well as a small amount of thetrans-isomer of the starting material, were obtained. The nature of the products obtained from the POPC-NO2 reaction depends on the concentration of NO2 as well as whether air is present. At low NO2 concentrations (PNO 2/N 2O4≤3.8 Torr) in air or in helium, thetrans-isomer of POPC was formed almost exclusively. At higher NO2 concentrations (PNO 2/N2O4≥20 Torr) in helium, the dinitro, vinyl nitro and nitro alcohol derivatives were formed. In the presence of air (or 24%18O2 in helium), a nitronitrate and a dinitronitrate were additional products. Mechanisms for the formation of the observed products and implications for the inhalation of oxides of nitrogen are discussed.

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Abbreviations

ATR:

attenuated total reflectance

DOPC:

1,2-dioleoyl-sn-glycero-3-phosphocholine

FAB-MS:

fast atom bombardment mass spectrometry

FTIR:

Fourier transform infrared

GC:

gas chromatography

HPLC:

high performance liquid chromatography

KHP:

potassium hydrogen phthalate

NOx :

oxides of nitrogen

PEPC:

1-palmitoyl-2-elaidoyl-sn-glycero-3-phosphocholine

POPOC:

1-palmitoyl-2-oleoyl-sn-glycero-phosphocholine

PS:

pulmonary surfactant.

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  1. Department of Chemistry and Biochemistry, California State University, 92634, Fullerton, California

    C. C. Lai & B. J. Finlayson-Pitts

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  1. C. C. Lai
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Lai, C.C., Finlayson-Pitts, B.J. Reactions of dinitrogen pentoxide and nitrogen dioxide with 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine. Lipids 26, 306–314 (1991). https://doi.org/10.1007/BF02537142

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  • DOI: https://doi.org/10.1007/BF02537142

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