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
Aug 1, 1992·Carcinogenesis·P FerrantiA Malorni
Mar 1, 1994·Chemical Research in Toxicology·J P Lepoittevin, A T Karlberg
Apr 11, 2001·The Journal of Biological Chemistry·C Giulivi, K J Davies
Jun 21, 2001·Contact Dermatitis·A M NilssonA T Karlberg
Oct 31, 2001·Contact Dermatitis·S C RastogiD A Basketter
Jun 27, 2002·Contact Dermatitis·Maria SköldAnn-Therese Karlberg
Oct 26, 2002·Journal of the American Academy of Dermatology·Mihály MaturaAnn-Therese Karlberg
Nov 20, 2002·Chemical Research in Toxicology·A A ShvedovaM R Gunther
Dec 9, 2003·Amino Acids·C GiuliviK J A Davies
Dec 21, 2004·Chemical Research in Toxicology·Maria SköldAnn-Therese Karlberg
Jun 4, 2005·Contact Dermatitis·Mihaly MaturaAnn-Therese Karlberg
Sep 30, 2005·Contact Dermatitis·Maja DivkovicDavid A Basketter
Sep 9, 2006·Contact Dermatitis·Johanna Bråred ChristenssonAnn-Therese Karlberg
Jan 20, 2007·Carcinogenesis·A R MurrayA A Shvedova
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
Jul 4, 2008·Chemical Research in Toxicology·Staffan JohanssonAnna Börje
Dec 17, 2008·Contact Dermatitis·Johanna Bråred ChristenssonAnn-Therese Karlberg
Sep 4, 2009·Chemical Research in Toxicology·Staffan JohanssonAnna Börje
Citations
Oct 27, 2015·Chemical Research in Toxicology·Ann-Therese KarlbergLina Hagvall
Jun 3, 2016·Contact Dermatitis·Niels Højsager BennikeJeanne D Johansen
Jan 18, 2017·Contact Dermatitis·Ann-Therese Karlberg
Jun 29, 2016·Journal of Cellular Biochemistry·Li Xiao, Nobuhiko Miwa
Feb 19, 2010·Chemical Research in Toxicology·Staffan G H JohanssonAnna Börje
Mar 5, 2011·Chemical Research in Toxicology·Ida B NiklassonAnn-Therese Karlberg
Jun 9, 2011·The Journal of Organic Chemistry·Dany KaoElena Giménez-Arnau
Sep 10, 2014·Chemical Research in Toxicology·Tamara DelaineAnn-Therese Karlberg
Aug 10, 2011·Chemical Research in Toxicology·Lina HagvallAnna Börje
Dec 22, 2012·Chemical Research in Toxicology·Karim ElbayedJean-Pierre Lepoittevin