Specific adducts formed through a radical reaction between peptides and contact allergenic hydroperoxides

Chemical Research in Toxicology
Theres RedebyAnn-Therese Karlberg

Abstract

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 ammonium acetate buffer pH 7.4, for 3 h at 37 degrees C, 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 onl...Continue Reading

References

Mar 1, 1994·Chemical Research in Toxicology·J P Lepoittevin, A T Karlberg
Oct 31, 2001·Contact Dermatitis·S C RastogiD A Basketter
Oct 26, 2002·Journal of the American Academy of Dermatology·Mihály MaturaAnn-Therese Karlberg
Dec 9, 2003·Amino Acids·C GiuliviK J A Davies
Jun 4, 2005·Contact Dermatitis·Mihaly MaturaAnn-Therese Karlberg
Sep 9, 2006·Contact Dermatitis·Johanna Bråred ChristenssonAnn-Therese Karlberg
May 25, 2007·Journal of Molecular Biology·Stefan GrudzielanekRoland Winter
Oct 17, 2007·Contact Dermatitis·Jacob Pontoppidan ThyssenJeanne Duus Johansen
Dec 7, 2007·Chemical Research in Toxicology·Ann-Therese KarlbergJ Lars G Nilsson
Dec 17, 2008·Contact Dermatitis·Johanna Bråred ChristenssonAnn-Therese Karlberg

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Citations

Oct 27, 2015·Chemical Research in Toxicology·Ann-Therese KarlbergLina Hagvall
Jan 18, 2017·Contact Dermatitis·Ann-Therese Karlberg
Sep 10, 2014·Chemical Research in Toxicology·Tamara DelaineAnn-Therese Karlberg

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