Synthesis and Allergenic Potential of a 15-Hydroperoxyabietic Acid-like Model: Trapping of Radical Intermediates
1
Laboratoire de Dermatochimie associé au CNRS, Clinique Dermatologique, Université Louis Pasteur, CHU, F-67091 Strasbourg Cedex, France, and Dermatology Division, National Institute for Working Life, S-11279 Stockholm, Sweden
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Publication type: Journal Article
Publication date: 2000-09-21
scimago Q1
wos Q2
SJR: 0.957
CiteScore: 7.5
Impact factor: 3.8
ISSN: 0893228X, 15205010
General Medicine
Toxicology
Abstract
To better understand the skin sensitization mechanism of 15-hydroperoxyabietic acid-like compounds, 2-(1‘-hydroperoxy-1‘-methylethyl)-4a-methyl-3,4,4a,5,6,7-hexahydronaphthalene 7 was synthesized. The allergenic activity of this compound was tested on mice using the local lymph node assay, and further evaluated on guinea pigs using the Freund's complete adjuvant test. Using these methods, hydroperoxide 7 was found to be a strong sensitizer. Radical-trapping experiments were carried out on this compound in the presence of the spin-trapping agent, 1,1,3,3-tetramethylisoindolin-2-yloxyl 17, using light to induce radicals. The formation of carbon-centered radicals derived from compound 7 by intramolecular cyclization of an oxygen-centered radical was observed. The reaction of these intermediates with 17 gave various adducts in a very low yield, but a 1/1 mixture of diastereomers 18a and 18b (0.1% yield) was isolated and characterized, together with compound 19 (0.03% yield). The results suggest that carbon-ce...
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Total citations:
21
Citations from 2024:
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(4.76%)
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Mutterer V. et al. Synthesis and Allergenic Potential of a 15-Hydroperoxyabietic Acid-like Model: Trapping of Radical Intermediates // Chemical Research in Toxicology. 2000. Vol. 13. No. 10. pp. 1028-1036.
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Mutterer V., Arnau E. G., Karlberg A. T., Lepoittevin J. P. Synthesis and Allergenic Potential of a 15-Hydroperoxyabietic Acid-like Model: Trapping of Radical Intermediates // Chemical Research in Toxicology. 2000. Vol. 13. No. 10. pp. 1028-1036.
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RIS
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TY - JOUR
DO - 10.1021/tx9901433
UR - https://doi.org/10.1021/tx9901433
TI - Synthesis and Allergenic Potential of a 15-Hydroperoxyabietic Acid-like Model: Trapping of Radical Intermediates
T2 - Chemical Research in Toxicology
AU - Mutterer, Vincent
AU - Arnau, Elena Giménez
AU - Karlberg, Ann Therese
AU - Lepoittevin, Jean Pierre
PY - 2000
DA - 2000/09/21
PB - American Chemical Society (ACS)
SP - 1028-1036
IS - 10
VL - 13
SN - 0893-228X
SN - 1520-5010
ER -
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BibTex (up to 50 authors)
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@article{2000_Mutterer,
author = {Vincent Mutterer and Elena Giménez Arnau and Ann Therese Karlberg and Jean Pierre Lepoittevin},
title = {Synthesis and Allergenic Potential of a 15-Hydroperoxyabietic Acid-like Model: Trapping of Radical Intermediates},
journal = {Chemical Research in Toxicology},
year = {2000},
volume = {13},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/tx9901433},
number = {10},
pages = {1028--1036},
doi = {10.1021/tx9901433}
}
Cite this
MLA
Copy
Mutterer, Vincent, et al. “Synthesis and Allergenic Potential of a 15-Hydroperoxyabietic Acid-like Model: Trapping of Radical Intermediates.” Chemical Research in Toxicology, vol. 13, no. 10, Sep. 2000, pp. 1028-1036. https://doi.org/10.1021/tx9901433.