PMID- 21370839
OWN - NLM
STAT- MEDLINE
DCOM- 20110923
LR  - 20151119
IS  - 1520-5010 (Electronic)
IS  - 0893-228X (Linking)
VI  - 24
IP  - 4
DP  - 2011 Apr 18
TI  - Impact of a heteroatom in a structure-activity relationship study on analogues of 
      phenyl glycidyl ether (PGE) from epoxy resin systems.
PG  - 542-8
LID - 10.1021/tx100417r [doi]
AB  - Epoxy resins are among the most common causes of occupational contact dermatitis. 
      They are normally used in so-called epoxy resin systems (ERS). These commercial 
      products are combinations of epoxy resins, curing agents, modifiers, and reactive 
      diluents. The most frequently used resins are diglycidyl ethers based on 
      bisphenol A (DGEBA) and bisphenol F (DGEBF). In this study, we have investigated 
      the contact allergenic properties of a series of analogues to the reactive 
      diluent phenyl glycidyl ether (PGE), all with similar basic structures but with 
      varying heteroatoms or with no heteroatom present. 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 ca. 60% depletion when using either PGE, phenyl 2,3-epoxypropyl 
      sulfide (2), or N-(2,3-epoxypropyl)aniline (3), and only 15% when using 
      1,2-epoxy-4-phenylbutane (4) at the same time point. 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 all 
      investigated compounds containing a heteroatom in the alpha-position to the epoxide 
      were strong sensitizers, congruent with the reactivity data, indicating that the 
      impact of a heteroatom is crucial for the sensitizing capacity for this type of 
      epoxides.
FAU - Niklasson, Ida B
AU  - Niklasson IB
AD  - Department of Chemistry, Dermatochemistry and Skin Allergy, University of 
      Gothenburg, Gothenburg, Sweden.
FAU - Delaine, Tamara
AU  - Delaine T
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
DEP - 20110329
PL  - United States
TA  - Chem Res Toxicol
JT  - Chemical research in toxicology
JID - 8807448
RN  - 0 (Aniline 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  - 0 (Sulfides)
RN  - 44KJQ1655I (phenylglycidyl ether)
SB  - IM
MH  - Aniline Compounds/chemical synthesis/*chemistry/toxicity
MH  - Animals
MH  - Epoxy Compounds/chemical synthesis/*chemistry/toxicity
MH  - Epoxy Resins/*chemistry
MH  - Female
MH  - Lymph Nodes/drug effects
MH  - Mice
MH  - Mice, Inbred CBA
MH  - Oligopeptides/chemistry
MH  - Phenyl Ethers/*chemistry/toxicity
MH  - Structure-Activity Relationship
MH  - Sulfides/chemical synthesis/*chemistry/toxicity
EDAT- 2011/03/05 06:00
MHDA- 2011/09/29 06:00
CRDT- 2011/03/05 06:00
PHST- 2011/03/05 06:00 [entrez]
PHST- 2011/03/05 06:00 [pubmed]
PHST- 2011/09/29 06:00 [medline]
AID - 10.1021/tx100417r [doi]
PST - ppublish
SO  - Chem Res Toxicol. 2011 Apr 18;24(4):542-8. doi: 10.1021/tx100417r. Epub 2011 Mar 
      29.