PMID- 20059493
OWN - NLM
STAT- MEDLINE
DCOM- 20100518
LR  - 20161125
IS  - 1600-0536 (Electronic)
IS  - 0105-1873 (Linking)
VI  - 61
IP  - 6
DP  - 2009 Dec
TI  - Does the extreme skin sensitization potency of benzoquinone result from special 
      chemistry?
PG  - 332-6
LID - 10.1111/j.1600-0536.2009.01646.x [doi]
AB  - BACKGROUND: Benzoquinone is known to be an extreme skin sensitizer. Until now 
      there has been no consideration of whether it owes its extreme skin sensitization 
      potency to unique aspects of its chemistry or simply to its high reactivity as a 
      Michael acceptor. OBJECTIVES: To answer these questions, we have applied two 
      mechanistic approaches to estimate a theoretical potency value for benzoquinone. 
      PATIENTS/METHODS: A mechanistic read-across (MRA) approach, using known potency 
      data for moderate sensitizers in the Michael acceptor domain, and a published 
      quantitative mechanistic model (QMM) for skin sensitization potency of Michael 
      acceptors, all in the moderate and weak range, were used. RESULTS: The 
      read-across approach gives a theoretical local lymph node assay (LLNA) EC3 value 
      of 0.04%, and the QMM approach gives a theoretical value of 0.013%, compared with 
      an experimental value of 0.010%. CONCLUSIONS: The good agreement between the 
      theoretical and experimental EC3 values supports the strength of the MRA and QMM 
      approaches, and provides strong evidence that the extreme sensitization potency 
      of benzoquinone can be attributed solely to its high reactivity as a Michael 
      acceptor.
FAU - Roberts, David W
AU  - Roberts DW
AD  - School of Pharmacy & Biomolecular Sciences, Liverpool John Moores University, 
      Liverpool, L3 3AF UK. d.w.roberts@ljmu.ac.uk
FAU - Aptula, Aynur O
AU  - Aptula AO
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PL  - England
TA  - Contact Dermatitis
JT  - Contact dermatitis
JID - 7604950
RN  - 0 (Allergens)
RN  - 0 (Benzoquinones)
RN  - 3T006GV98U (quinone)
SB  - IM
MH  - Allergens/*chemistry
MH  - Benzoquinones/*chemistry
MH  - Databases, Factual
MH  - Dermatitis, Allergic Contact/*etiology
MH  - Local Lymph Node Assay
MH  - Models, Theoretical
MH  - Molecular Structure
MH  - Predictive Value of Tests
MH  - Quantitative Structure-Activity Relationship
MH  - Skin/*drug effects
MH  - Toxicity Tests
EDAT- 2010/01/12 06:00
MHDA- 2010/05/19 06:00
CRDT- 2010/01/12 06:00
PHST- 2010/01/12 06:00 [entrez]
PHST- 2010/01/12 06:00 [pubmed]
PHST- 2010/05/19 06:00 [medline]
AID - COD1646 [pii]
AID - 10.1111/j.1600-0536.2009.01646.x [doi]
PST - ppublish
SO  - Contact Dermatitis. 2009 Dec;61(6):332-6. doi: 10.1111/j.1600-0536.2009.01646.x.