Formation of lipid adducts by carbon tetrachloride

S. G. Britt, Ghulam Ansari

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Toxicity of carbon tetrachloride (CCl4) is mediated by the formation of a trichloromethyl radical (·CCl3) through one electron reduction by cytochrome P-450. The ·CCl3 radical thus formed may undergo further transformation to reactive metabolites or may modify biomolecules. To elucidate the mechanism by which CCl4 reacts with lipids, a benzoyl peroxide initiated free radical addition of CCl4 to methyl oleate was studied. Methyl oleate adducts of CCl4 were separated by high performance liquid chromatography into these fractions. Ammonia chemical ionization mass spectrometry and the 20 eV electron impact mass spectra of all three fractions indicated molecular weight of 448 and the presence of four chlorine atoms. Proton magnetic resonance spectroscopy indicated that fraction 1 is a mixture while fractions 2 and 3 are isomeric products from the addition of chlorine and trichloromethyl across the double bond of methyl oleate. This study demonstrates the structural complexity of lipids covalently modified by CCl4. Formation of such adducts may alter membrane structure and function, and thus contriubte to the observed toxicity of CCl4.

Original languageEnglish (US)
Pages (from-to)305-311
Number of pages7
JournalClinical Chemistry and Enzymology Communications
Volume1
Issue number5-6
StatePublished - 1989

Fingerprint

Carbon Tetrachloride
Chlorine
Lipids
Toxicity
Benzoyl Peroxide
Electrons
Magnetic resonance spectroscopy
Membrane structures
High performance liquid chromatography
Biomolecules
Metabolites
Ammonia
Cytochrome P-450 Enzyme System
Free Radicals
Ionization
Mass spectrometry
Mass Spectrometry
Molecular Weight
Molecular weight
High Pressure Liquid Chromatography

ASJC Scopus subject areas

  • Clinical Biochemistry

Cite this

Formation of lipid adducts by carbon tetrachloride. / Britt, S. G.; Ansari, Ghulam.

In: Clinical Chemistry and Enzymology Communications, Vol. 1, No. 5-6, 1989, p. 305-311.

Research output: Contribution to journalArticle

@article{f1064a5647c84ae8aef4f3119772f463,
title = "Formation of lipid adducts by carbon tetrachloride",
abstract = "Toxicity of carbon tetrachloride (CCl4) is mediated by the formation of a trichloromethyl radical (·CCl3) through one electron reduction by cytochrome P-450. The ·CCl3 radical thus formed may undergo further transformation to reactive metabolites or may modify biomolecules. To elucidate the mechanism by which CCl4 reacts with lipids, a benzoyl peroxide initiated free radical addition of CCl4 to methyl oleate was studied. Methyl oleate adducts of CCl4 were separated by high performance liquid chromatography into these fractions. Ammonia chemical ionization mass spectrometry and the 20 eV electron impact mass spectra of all three fractions indicated molecular weight of 448 and the presence of four chlorine atoms. Proton magnetic resonance spectroscopy indicated that fraction 1 is a mixture while fractions 2 and 3 are isomeric products from the addition of chlorine and trichloromethyl across the double bond of methyl oleate. This study demonstrates the structural complexity of lipids covalently modified by CCl4. Formation of such adducts may alter membrane structure and function, and thus contriubte to the observed toxicity of CCl4.",
author = "Britt, {S. G.} and Ghulam Ansari",
year = "1989",
language = "English (US)",
volume = "1",
pages = "305--311",
journal = "Clinical Chemistry and Enzymology Communications",
issn = "0892-2187",
publisher = "Harwood Academic Publishers",
number = "5-6",

}

TY - JOUR

T1 - Formation of lipid adducts by carbon tetrachloride

AU - Britt, S. G.

AU - Ansari, Ghulam

PY - 1989

Y1 - 1989

N2 - Toxicity of carbon tetrachloride (CCl4) is mediated by the formation of a trichloromethyl radical (·CCl3) through one electron reduction by cytochrome P-450. The ·CCl3 radical thus formed may undergo further transformation to reactive metabolites or may modify biomolecules. To elucidate the mechanism by which CCl4 reacts with lipids, a benzoyl peroxide initiated free radical addition of CCl4 to methyl oleate was studied. Methyl oleate adducts of CCl4 were separated by high performance liquid chromatography into these fractions. Ammonia chemical ionization mass spectrometry and the 20 eV electron impact mass spectra of all three fractions indicated molecular weight of 448 and the presence of four chlorine atoms. Proton magnetic resonance spectroscopy indicated that fraction 1 is a mixture while fractions 2 and 3 are isomeric products from the addition of chlorine and trichloromethyl across the double bond of methyl oleate. This study demonstrates the structural complexity of lipids covalently modified by CCl4. Formation of such adducts may alter membrane structure and function, and thus contriubte to the observed toxicity of CCl4.

AB - Toxicity of carbon tetrachloride (CCl4) is mediated by the formation of a trichloromethyl radical (·CCl3) through one electron reduction by cytochrome P-450. The ·CCl3 radical thus formed may undergo further transformation to reactive metabolites or may modify biomolecules. To elucidate the mechanism by which CCl4 reacts with lipids, a benzoyl peroxide initiated free radical addition of CCl4 to methyl oleate was studied. Methyl oleate adducts of CCl4 were separated by high performance liquid chromatography into these fractions. Ammonia chemical ionization mass spectrometry and the 20 eV electron impact mass spectra of all three fractions indicated molecular weight of 448 and the presence of four chlorine atoms. Proton magnetic resonance spectroscopy indicated that fraction 1 is a mixture while fractions 2 and 3 are isomeric products from the addition of chlorine and trichloromethyl across the double bond of methyl oleate. This study demonstrates the structural complexity of lipids covalently modified by CCl4. Formation of such adducts may alter membrane structure and function, and thus contriubte to the observed toxicity of CCl4.

UR - http://www.scopus.com/inward/record.url?scp=0024416366&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0024416366&partnerID=8YFLogxK

M3 - Article

VL - 1

SP - 305

EP - 311

JO - Clinical Chemistry and Enzymology Communications

JF - Clinical Chemistry and Enzymology Communications

SN - 0892-2187

IS - 5-6

ER -