Production of the Criegee ozonide during the ozonation of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine liposomes

Journal Article · Tue Dec 01 04:00:00 EST 1992 · Lipids; (United States)

DOI:https://doi.org/10.1007/BF02535571· OSTI ID:6750558

Squadrito, G L; Uppu, R M; Cueto, R; Pryor, W A ^[1]

---

1. Louisiana State Univ., Baton Rouge (United States)

It is likely that Criegee ozonides are formed in small amounts in the lungs of animals breathing ozone-containing air. This makes these compounds potential candidates to act as secondary toxins which relay the toxic effects of ozone deeper into lung tissue than ozone itself could penetrate. Therefore, we have determined the yields of Criegee ozonides from unsaturated lipids in liposomal systems as a model of the types of yields of Criegee ozonides that might be expected both in the lung lining fluid layer and in biological membranes. Ozonation of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine liposomes produced both cis- and trans-Criegee ozonides. These ozonides have been isolated by solid phase extraction and high-performance liquid chromatography of the ozonized lipid, and the products have been identified by two-dimensional 1H nuclear magnetic resonance. The combined yield of the cis- and trans-Criegee ozonides is 10.7 +/- 2.8% (avg. +/- SD, n = 7) with small unilamellar liposomes and 10.6 +/- 2.7% (n = 3) with large multilamellar liposomes. We had previously reported that ozonation of methyl oleate in sodium dodecylsulfate micelles also produces an 11% yield of the Criegee ozonides. Thus, ozonation in a variety of models gives about 11% of the Criegee ozonide, suggesting that these products also would be formed in small but significant amounts in the lungs of animals breathing polluted air. Further research on the pharmacokinetics and possible toxicity of the Criegee ozonides of fatty acids is suggested.

• OSTI ID: 6750558
• Journal Information: Lipids; (United States), Journal Name: Lipids; (United States) Vol. 27:12; ISSN 0024-4201; ISSN LPDSAP
• Country of Publication: United States
• Language: English

Related Subjects

550200 -- Biochemistry
560300* -- Chemicals Metabolism & Toxicology
59 BASIC BIOLOGICAL SCIENCES
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ANTIGENS
BIOCHEMICAL REACTION KINETICS
BIOLOGICAL MODELS
BODY
CHROMATOGRAPHY
ENVIRONMENTAL EXPOSURE PATHWAY
ESTERS
EXTRACTION
HAZARDOUS MATERIALS
KINETICS
LIPIDS
LIPOSOMES
LIQUID COLUMN CHROMATOGRAPHY
LUNGS
MAGNETIC RESONANCE
MATERIALS
NUCLEAR MAGNETIC RESONANCE
ORGANIC COMPOUNDS
ORGANIC PHOSPHORUS COMPOUNDS
ORGANS
OZONE
PHOSPHOLIPIDS
REACTION KINETICS
RESONANCE
RESPIRATORY SYSTEM
SEPARATION PROCESSES
TOXIC MATERIALS
TOXICITY
TOXINS