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Specific Adducts Fo...
Specific Adducts Formed through a Radical Reaction between Peptides and Contact Allergenic Hydroperoxides
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- Redeby, Theres, 1973 (author)
- Gothenburg University,Göteborgs universitet,Stockholms universitet,Institutionen för analytisk kemi,Institutionen för kemi,Department of Chemistry
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- Nilsson, Ulrika (author)
- Stockholms universitet,Institutionen för analytisk kemi
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- Altamore, Timothy A. (author)
- Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry
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- Ilag, Leopold (author)
- Stockholms universitet,Institutionen för analytisk kemi
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- Ambrosi, Annalisa (author)
- Stockholms universitet,Institutionen för analytisk kemi
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- Broo, Kerstin, 1970 (author)
- Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry
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- Börje, Anna, 1961 (author)
- Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry
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- Karlberg, Ann-Therese, 1947 (author)
- Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry
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(creator_code:org_t)
- 2009-11-23
- 2010
- English.
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In: Chemical Research in Toxicology. - : American Chemical Society (ACS). - 0893-228X .- 1520-5010. ; 23:1, s. 203-210
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
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- The first step in the development of contact allergy (allergic contact dermatitis) includes the penetration of an allergy-causing chemical (hapten) into the skin, where it binds to macromolecules such as proteins. The protein-hapten adduct is then recognized by the immune system as foreign to the body. For hydroperoxides, no relevant hapten target proteins or protein-hapten adducts have so far been identified. In this work, bovine insulin and human angiotensin I were used as model peptides to investigate the haptenation mechanism of three hydroperoxide haptens: (5R)-5-isopropenyl-2-methyl-2-cyclohexene-1-hydroperoxide (Lim-2-OOH), cumene hydroperoxide (CumOOH), and 1-(1-hydroperoxy-1-methylethyl) cyclohexene (CycHexOOH). These hydroperoxides are expected to react via a radical mechanism, for which 5,10,15,20-tetraphenyl-21H,23H-porphine iron(III) chloride (Fe(III)TPPCl) was used as a radical initiator. The reactions were carried out in 1:1 ethanol/10 mM amonium acetate buffer pH 7.4, for 3 h at 37 T, and the reaction products were either enzymatically digested or analyzed directly by MALDI/TOF-MS, HPLC/MS/MS, and 2D gel electrophoresis. Both hydroperoxide-specific and unspecific reaction products were detected, but only it) the presence of the iron catalyst. In the absence of catalyst, the hydroperoxides remained unreacted. This suggests that the hydroperoxides call enter into the skin and remain inert until activated. Through the detection of a Lim-2-OOH adduct bound at the first histidine (of two) of angiotensin I, it was confirmed that hydroperoxides have the potential to form specific antigens in contact allergy.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
Keyword
- NATURAL SCIENCES
- NATURVETENSKAP
Publication and Content Type
- ref (subject category)
- art (subject category)
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- By the author/editor
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Redeby, Theres, ...
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Nilsson, Ulrika
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Altamore, Timoth ...
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Ilag, Leopold
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Ambrosi, Annalis ...
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Broo, Kerstin, 1 ...
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Börje, Anna, 196 ...
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Karlberg, Ann-Th ...
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- NATURAL SCIENCES
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NATURAL SCIENCES
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and Chemical Science ...
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Chemical Researc ...
- By the university
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Stockholm University
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University of Gothenburg