PMID- 19725531
OWN - NLM
STAT- MEDLINE
DCOM- 20100222
LR  - 20181231
IS  - 1520-5010 (Electronic)
IS  - 0893-228X (Linking)
VI  - 22
IP  - 11
DP  - 2009 Nov
TI  - Reduced sensitizing capacity of epoxy resin systems: a structure-activity 
      relationship study.
PG  - 1787-94
LID - 10.1021/tx900193s [doi]
AB  - Epoxy resins can be prepared from numerous chemical compositions. Until recently, 
      alternatives to epoxy resins based on diglycidyl ethers of bisphenol A (DGEBA) or 
      bisphenol F (DGEBF) monomers have not received commercial interest, but are 
      presently doing so, as epoxy resins with various properties are desired. Epoxy 
      resin systems are known to cause allergic contact dermatitis because of contents 
      of uncured monomers, reactive diluents, and hardeners. Reactive diluents, for 
      example, glycidyl ethers, which also contain epoxide moieties, are added to 
      reduce viscosity and improve polymerization. We have investigated the contact 
      allergenic properties of a series of six analogues to phenyl glycidyl ether 
      (PGE), all with similar basic structures but with varying carbon chain lengths 
      and degrees of saturation. The chemical reactivity of the compounds in the test 
      series toward the hexapeptide H-Pro-His-Cys-Lys-Arg-Met-OH was investigated. All 
      epoxides were shown to bind covalently to both cysteine and proline residues. The 
      percent depletion of nonreacted peptide was also studied resulting in 88% 
      depletion when using PGE and 46% when using butyl glycidyl ether (5) at the same 
      time point, thus revealing a large difference between the fastest and the slowest 
      reacting epoxide. The skin sensitization potencies of the epoxides using the 
      murine local lymph node assay (LLNA) were evaluated in relation to the observed 
      physicochemical and reactivity properties. To enable determination of statistical 
      significance between structurally closely related compounds, a nonpooled LLNA was 
      performed. It was found that the compounds investigated ranged from strong to 
      weak sensitizers, congruent with the reactivity data, indicating that even small 
      changes in chemical structure result in significant differences in sensitizing 
      capacity.
FAU - Niklasson, Ida B
AU  - Niklasson IB
AD  - Department of Chemistry, Dermatochemistry and Skin Allergy, University of 
      Gothenburg, SE-412 96 Gothenburg, Sweden.
FAU - Broo, Kerstin
AU  - Broo K
FAU - Jonsson, Charlotte
AU  - Jonsson C
FAU - Luthman, Kristina
AU  - Luthman K
FAU - Karlberg, Ann-Therese
AU  - Karlberg AT
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - United States
TA  - Chem Res Toxicol
JT  - Chemical research in toxicology
JID - 8807448
RN  - 0 (Benzhydryl Compounds)
RN  - 0 (Epoxy Compounds)
RN  - 0 (Epoxy Resins)
RN  - 0 (H-Pro-His-Cys-Lys-Arg-Met-OH)
RN  - 0 (Oligopeptides)
RN  - 0 (Phenyl Ethers)
RN  - 44KJQ1655I (phenylglycidyl ether)
RN  - F3XRM1NX4H (2,2-bis(4-glycidyloxyphenyl)propane)
RN  - V3625OQU1K (bisphenol F diglycidyl ether)
SB  - IM
MH  - Animals
MH  - Benzhydryl Compounds
MH  - Chromatography, High Pressure Liquid
MH  - Dermatitis, Allergic Contact/etiology
MH  - Epoxy Compounds/chemistry/toxicity
MH  - Epoxy Resins/*chemistry/toxicity
MH  - Female
MH  - Local Lymph Node Assay
MH  - Mice
MH  - Oligopeptides/chemistry
MH  - Phenyl Ethers/chemistry/toxicity
MH  - Spectrometry, Mass, Electrospray Ionization
MH  - Structure-Activity Relationship
EDAT- 2009/09/04 06:00
MHDA- 2010/02/23 06:00
CRDT- 2009/09/04 06:00
PHST- 2009/09/04 06:00 [entrez]
PHST- 2009/09/04 06:00 [pubmed]
PHST- 2010/02/23 06:00 [medline]
AID - 10.1021/tx900193s [doi]
PST - ppublish
SO  - Chem Res Toxicol. 2009 Nov;22(11):1787-94. doi: 10.1021/tx900193s.