PMID- 18704111
OWN - NLM
STAT- MEDLINE
DCOM- 20090106
LR  - 20131121
IS  - 1523-1747 (Electronic)
IS  - 0022-202X (Linking)
VI  - 129
IP  - 1
DP  - 2009 Jan
TI  - Skin sensitization to p-phenylenediamine: the diverging roles of oxidation and 
      N-acetylation for dendritic cell activation and the immune response.
PG  - 99-109
LID - 10.1038/jid.2008.209 [doi]
AB  - Skin is a target of allergic reactions to aromatic amine hair dye precursors, 
      such as p-phenylenediamine (PPD). As conversion of PPD on or in the skin is 
      expected to be required for the induction of allergic contact dermatitis, we 
      analyzed the role of oxidation and N-acetylation as major transformation steps. 
      PPD and its oxidative and N-acetylated derivatives were tested for their 
      sensitizing potential in vitro using a dendritic cell (DC) activation assay and 
      in vivo using the local lymph node assay (LLNA). PPD did not induce relevant DC 
      activation but induced a positive LLNA response. In contrast, DC activation was 
      obtained when PPD was chemically pre-oxidized or after air oxygen exposure. Under 
      both conditions, the potent sensitizing PPD oxidation product Bandrowski's base 
      was identified along with other di- and trimeric species, indicating that PPD 
      oxidation products provide an effective immune stimulation (danger signal). In 
      contrast mono- and diacetylated PPD did not induce DC activation or a positive 
      LLNA response. We conclude that dermal N-acetylation of PPD competes with the 
      formation of oxidized PPD whereas skin exposure conditions allowing 
      auto-oxidation, as in the LLNA, provide an effective danger signal necessary to 
      induce skin sensitization to PPD.
FAU - Aeby, Pierre
AU  - Aeby P
AD  - Procter and Gamble Co., Wella-Cosmital, Marly, Switzerland.
FAU - Sieber, Thomas
AU  - Sieber T
FAU - Beck, Heinz
AU  - Beck H
FAU - Gerberick, G Frank
AU  - Gerberick GF
FAU - Goebel, Carsten
AU  - Goebel C
LA  - eng
PT  - Journal Article
DEP - 20080814
PL  - United States
TA  - J Invest Dermatol
JT  - The Journal of investigative dermatology
JID - 0426720
RN  - 0 (Coloring Agents)
RN  - 0 (Culture Media)
RN  - 0 (Phenylenediamines)
RN  - S88TT14065 (Oxygen)
RN  - U770QIT64J (4-phenylenediamine)
SB  - IM
MH  - Acetylation
MH  - Air
MH  - Animals
MH  - Coloring Agents/pharmacology
MH  - Culture Media/metabolism
MH  - Dendritic Cells/*cytology
MH  - Humans
MH  - Immune System
MH  - Lymph Nodes/pathology
MH  - Mice
MH  - Models, Biological
MH  - Monocytes/metabolism
MH  - Oxygen/metabolism
MH  - Phenylenediamines/*pharmacology
MH  - Signal Transduction
EDAT- 2008/08/16 09:00
MHDA- 2009/01/07 09:00
CRDT- 2008/08/16 09:00
PHST- 2008/08/16 09:00 [entrez]
PHST- 2008/08/16 09:00 [pubmed]
PHST- 2009/01/07 09:00 [medline]
AID - S0022-202X(15)34067-7 [pii]
AID - 10.1038/jid.2008.209 [doi]
PST - ppublish
SO  - J Invest Dermatol. 2009 Jan;129(1):99-109. doi: 10.1038/jid.2008.209. Epub 2008 
      Aug 14.