PMID- 18759874
OWN - NLM
STAT- MEDLINE
DCOM- 20081210
LR  - 20131121
IS  - 1600-0536 (Electronic)
IS  - 0105-1873 (Linking)
VI  - 59
IP  - 2
DP  - 2008 Aug
TI  - Zinc diethyldithiocarbamate allergenicity: potential haptenation mechanisms.
PG  - 79-89
LID - 10.1111/j.1600-0536.2008.01399.x [doi]
AB  - BACKGROUND: Zinc diethyldithiocarbamate (ZDEC) and its disulfide, 
      tetraethylthiuram disulfide (TETD), are rubber accelerators and contact allergens 
      that cross-react in some individuals. OBJECTIVE: This study explored potential 
      protein haptenation mechanisms of ZDEC and its oxidation products. METHODS: ZDEC 
      oxidation/reduction products and sites of protein binding were assessed using 
      high-performance liquid chromatography and mass spectrometry. The murine local 
      lymph node assay (LLNA) was employed to probe haptenation mechanisms of ZDEC by 
      examining its allergenicity along with its oxidation products and through 
      elimination of oxidation and chelation mechanisms by substituting cobalt for zinc 
      [cobalt (II) dithiocarbamate, CoDEC]. RESULTS: Oxidation of ZDEC by hypochlorous 
      acid (bleach, HOCl), iodine, or hydrogen peroxide resulted in production of TETD, 
      tetraethylthiocarbamoyl disulfide, and tetraethyldicarbamoyl disulfide (TEDCD). 
      Albumin thiols reduced TETD with subsequent mixed disulfide 
      formation/haptenation. ZDEC directly chelated the copper ion on the active site 
      of the superoxide dismutase, whereas CoDEC did not bind to Cu proteins or form 
      mixed disulfides with free thiols. ZDEC, sodium diethyldithiocarbamate, TEDCD, 
      and TETD were all positive in the LLNA except CoDEC, which was non-allergenic. 
      CONCLUSION: The thiol is the critical functional group in ZDEC's allergenicity, 
      and haptenation is predominantly through chelation of metalloproteins and 
      formation of mixed disulfides.
FAU - Chipinda, Itai
AU  - Chipinda I
AD  - Allergy and Clinical Immunology Branch, Health Effects Laboratory Division, 
      National Institute for Occupational Safety and Health, Morgantown, WV 26505-2888, 
      USA. ichipinda@cdc.gov
FAU - Hettick, Justin M
AU  - Hettick JM
FAU - Simoyi, Reuben H
AU  - Simoyi RH
FAU - Siegel, Paul D
AU  - Siegel PD
LA  - eng
GR  - Y1-ES0001-06/ES/NIEHS NIH HHS/United States
PT  - Journal Article
PT  - Research Support, N.I.H., Extramural
PT  - Research Support, U.S. Gov't, Non-P.H.S.
PL  - England
TA  - Contact Dermatitis
JT  - Contact dermatitis
JID - 7604950
RN  - 0 (Allergens)
RN  - 0 (Haptens)
RN  - 99Z2744345 (Ditiocarb)
RN  - TR3MLJ1UAI (Disulfiram)
SB  - IM
MH  - Allergens/*chemistry
MH  - Animals
MH  - Chromatography, High Pressure Liquid
MH  - Cross-Sectional Studies
MH  - Dermatitis, Allergic Contact/*etiology/pathology
MH  - Disulfiram/*chemistry
MH  - Ditiocarb/*adverse effects/*chemistry
MH  - Female
MH  - Haptens/*chemistry
MH  - Mice
MH  - Mice, Inbred BALB C
MH  - Oxidation-Reduction
EDAT- 2008/09/02 09:00
MHDA- 2008/12/17 09:00
CRDT- 2008/09/02 09:00
PHST- 2008/09/02 09:00 [pubmed]
PHST- 2008/12/17 09:00 [medline]
PHST- 2008/09/02 09:00 [entrez]
AID - COD1399 [pii]
AID - 10.1111/j.1600-0536.2008.01399.x [doi]
PST - ppublish
SO  - Contact Dermatitis. 2008 Aug;59(2):79-89. doi: 10.1111/j.1600-0536.2008.01399.x.