PMID- 30543284
OWN - NLM
STAT- MEDLINE
DCOM- 20191219
LR  - 20191219
IS  - 1520-5010 (Electronic)
IS  - 0893-228X (Linking)
VI  - 32
IP  - 1
DP  - 2019 Jan 22
TI  - Development of New Epoxy Resin Monomers - A Delicate Balance between Skin Allergy 
      and Polymerization Properties.
PG  - 57-66
LID - 10.1021/acs.chemrestox.8b00169 [doi]
AB  - Epoxy resin monomers (ERMs) are used as building blocks for thermosetting 
      polymers in applications where strong, flexible, and lightweight materials are 
      required. Most epoxy resins are polymers of diglycidyl ether of bisphenol A 
      (DGEBA). It is highly allergenic and causes occupational allergic contact 
      dermatitis and contact allergy in the general population. Thus, measures to 
      prevent exposure by protective clothing and education are not enough. This work 
      describes a continuation of our research aiming at reducing the skin-sensitizing 
      potency of ERMs while maintaining the ability to form polymers. Alternative ERMs 
      were designed and synthesized whereafter the sensitizing potency was determined 
      using the murine local lymph node assay (LLNA). The reactivity of the diepoxides 
      toward a nucleophilic peptide was investigated, and the differences in reactivity 
      explained using computational studies. The diepoxides were reacted with 
      triethylenetetramine, and the formed polymers were tested for technical 
      applicability using thermogravimetric analysis. We had previously shown that the 
      absence of an oxygen atom in the side chains or removal of aromaticity reduced 
      the sensitizing potency compared to that of DGEBA. Thus, a cycloaliphatic 
      analogue 1 of DGEBA without ether oxygen in the side chains was considered 
      promising and was synthesized. As predicted, the sensitizing potency was 
      considerably reduced (10 times) compared to that of DGEBA. However, the technical 
      properties of the polymer of this compound were not considered sufficient. More 
      polar aromatic analogues were investigated, but they could not compete with our 
      previously described ERMs regarding polymerization properties and with 1 
      regarding low skin sensitization properties. Development of alternative epoxy 
      materials is a delicate balance between allergenic activity and polymerization 
      properties. Tuning of structural properties together with investigation of 
      polymerization conditions combined with skin sensitization studies should be used 
      in industrial research and development. ERM 1 could be used as a lead compound 
      for further studies of aliphatic ERMs.
FAU - Ponting, David J
AU  - Ponting DJ
AD  - Department of Chemistry and Molecular Biology, Dermatochemistry , University of 
      Gothenburg , SE-412 96 Gothenburg , Sweden.
FAU - Ortega, Miguel A
AU  - Ortega MA
AD  - Department of Chemistry and Molecular Biology, Dermatochemistry , University of 
      Gothenburg , SE-412 96 Gothenburg , Sweden.
FAU - Niklasson, Ida B
AU  - Niklasson IB
AD  - Department of Chemistry and Molecular Biology, Dermatochemistry , University of 
      Gothenburg , SE-412 96 Gothenburg , Sweden.
FAU - Karlsson, Isabella
AU  - Karlsson I
AD  - Department of Chemistry and Molecular Biology, Dermatochemistry , University of 
      Gothenburg , SE-412 96 Gothenburg , Sweden.
FAU - Seifert, Tina
AU  - Seifert T
AD  - Department of Chemistry and Molecular Biology, Medicinal Chemistry , University 
      of Gothenburg , SE-412 96 Gothenburg , Sweden.
FAU - Steen, Johanna
AU  - Steen J
AD  - Department of Chemistry and Molecular Biology, Dermatochemistry , University of 
      Gothenburg , SE-412 96 Gothenburg , Sweden.
FAU - Luthman, Kristina
AU  - Luthman K
AD  - Department of Chemistry and Molecular Biology, Medicinal Chemistry , University 
      of Gothenburg , SE-412 96 Gothenburg , Sweden.
FAU - Karlberg, Ann-Therese
AU  - Karlberg AT
AUID- ORCID: 0000-0003-2691-3644
AD  - Department of Chemistry and Molecular Biology, Dermatochemistry , University of 
      Gothenburg , SE-412 96 Gothenburg , Sweden.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20181231
PL  - United States
TA  - Chem Res Toxicol
JT  - Chemical research in toxicology
JID - 8807448
RN  - 0 (Benzhydryl Compounds)
RN  - 0 (Epoxy Compounds)
RN  - F3XRM1NX4H (2,2-bis(4-glycidyloxyphenyl)propane)
SB  - IM
MH  - Animals
MH  - Benzhydryl Compounds/chemical synthesis/chemistry/*pharmacology
MH  - Density Functional Theory
MH  - *Drug Hypersensitivity
MH  - Epoxy Compounds/chemical synthesis/chemistry/*pharmacology
MH  - Female
MH  - Mice
MH  - Mice, Inbred CBA
MH  - Molecular Structure
MH  - Polymerization/*drug effects
MH  - Skin/*drug effects
EDAT- 2018/12/14 06:00
MHDA- 2019/12/20 06:00
CRDT- 2018/12/14 06:00
PHST- 2018/12/14 06:00 [pubmed]
PHST- 2019/12/20 06:00 [medline]
PHST- 2018/12/14 06:00 [entrez]
AID - 10.1021/acs.chemrestox.8b00169 [doi]
PST - ppublish
SO  - Chem Res Toxicol. 2019 Jan 22;32(1):57-66. doi: 10.1021/acs.chemrestox.8b00169. 
      Epub 2018 Dec 31.