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Mechanism of the an...
Mechanism of the antigen formation of carvone and related alpha, beta-unsaturated ketones
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Nilsson, Anna-Malin (författare)
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Gafvert, Elisabeth (författare)
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Salvador, Lourdes (författare)
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Luthman, Kristina (författare)
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- Bruze, Magnus (författare)
- Lund University,Lunds universitet,Yrkes- och miljödermatologi,Forskargrupper vid Lunds universitet,Occupational and Environmental Dermatology,Lund University Research Groups
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- Gruvberger, Birgitta (författare)
- Lund University,Lunds universitet,Institutionen för kliniska vetenskaper, Malmö,Medicinska fakulteten,Department of Clinical Sciences, Malmö,Faculty of Medicine
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Nilsson, J. Lars G. (författare)
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Karlberg, Ann-Therese (författare)
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(creator_code:org_t)
- Wiley, 2001
- 2001
- Engelska.
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Ingår i: Contact Dermatitis. - : Wiley. - 0105-1873 .- 1600-0536. ; 44:6, s. 347-356
- Relaterad länk:
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http://dx.doi.org/10...
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https://lup.lub.lu.s...
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https://doi.org/10.1...
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http://kipublication...
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Abstract
Ämnesord
Stäng
- In the present study, the mechanism for the antigen formation of alpha, beta-unsaturated ketones was investigated. A series of analogues of carvone ((5R)-5-isopropenyl-2-methyl-2-cyclohexenone) with altered chemical reactivity and with retained overall structure or with retained reactivity and altered three-dimensional structure were synthesized. These analogues were tested for cross-reactivity in carvone-sensitized animals. Cross-reactivity was observed for analogue 3 ((5R)-5-isopropyl-2-methyl-2-cyclohexen-1-one). No cross-reactions were observed for analogues 1 ((2R,5R)-5-isopropenyl-2-methyl cyclohexanone) and 4 ((5R)-2,3-dimethyl-5-isopropenyl-2-cyclohexene-1-one). Both those compounds also failed to induce sensitization. These findings demonstrate that alpha, beta-unsaturated ketones form antigens after a nucleophilic attack at the beta-carbon with soft nucleophiles such as thiol in cysteine and not with the formation of a Schiff's base after a nucleophilic attack at the carbonyl carbon with nitrogen nucleophiles. Furthermore, no cross-reactivity was observed between R- and S-carvone indicating the importance of the 3-dimensional structure of haptens (and antigens) in T-cell recognition. The analogues were also tested for cross-reactivity on patients allergic to carvone. The results from the animal study were confirmed.
Ämnesord
- MEDICIN OCH HÄLSOVETENSKAP -- Klinisk medicin -- Dermatologi och venereologi (hsv//swe)
- MEDICAL AND HEALTH SCIENCES -- Clinical Medicine -- Dermatology and Venereal Diseases (hsv//eng)
Nyckelord
- allergic contact dermatitis
- carvone
- enantiospecificity
- Michael addition
- Schiff's base
- structure-activity relationship
- α
- β-unsaturated ketones
Publikations- och innehållstyp
- art (ämneskategori)
- ref (ämneskategori)
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