PMID- 12488139
OWN - NLM
STAT- MEDLINE
DCOM- 20040128
LR  - 20190826
IS  - 0891-5849 (Print)
IS  - 0891-5849 (Linking)
VI  - 33
IP  - 12
DP  - 2002 Dec 15
TI  - Catalysis of catechol oxidation by metal-dithiocarbamate complexes in pesticides.
PG  - 1714-23
AB  - Dithiocarbamate (DTC)-based pesticides have been implicated in Parkinson's 
      disease (PD) through epidemiological links to increased risk of PD, clinical 
      reports of parkinsonism following occupational exposure to the DTC-based 
      pesticide maneb, and experimental studies showing dopaminergic neurodegeneration 
      with combined exposure of rats to maneb and paraquat. We hypothesize that the 
      manganese-ethylene-bis-dithiocarbamate (MnEBDC) complex in maneb may produce 
      oxidative stress by catalyzing catechol oxidation. We tested this hypothesis by 
      performing a structure-function analysis of metal-EBDC and 
      metal-diethyldithiocarbamate (DEDC) complexes of Mn2+, Zn2+, and Cu2+ to catalyze 
      oxidation of N-acetyldopamine (NA-DA) and 3,4-dihydroxyphenylacetic acid (DP) in 
      the presence and absence of N-acetylcysteine (NAC), a model of glutathione. Both 
      Mn-DTCs retained the capacity of the parent ion to catalyze one-electron 
      oxidation of NA-DA, but lost the ability to catalyze DP oxidation. Strikingly, 
      while Zn2+ did not catalyze catechol oxidation, both Zn-DTCs catalyzed 
      one-electron oxidation of NA-DA but not DP. While Cu2+ catalyzed oxidation of 
      both catechols, Cu-DTCs were inert. Similar results were obtained with MnEBDC and 
      dopamine or norepinephrine; however, zinc-ethylene-bis-dithiocarbamate was less 
      efficient at catalyzing oxidation of these catechols. Our results point to the 
      potential for manganese- and zinc-containing EBDC pesticides to promote oxidative 
      stress in catecholaminergic regions of the brain.
FAU - Fitsanakis, Vanessa A
AU  - Fitsanakis VA
AD  - Departments of Pathology and Pharmacology and Centers for Molecular Toxicology 
      and Molecular Neurosciences, Vanderbilt University Medical Center, Nashville, TN, 
      USA. tmontine@u.washington.edu
FAU - Amarnath, Venkataraman
AU  - Amarnath V
FAU - Moore, Joshua T
AU  - Moore JT
FAU - Montine, Kathleen S
AU  - Montine KS
FAU - Zhang, Jing
AU  - Zhang J
FAU - Montine, Thomas J
AU  - Montine TJ
LA  - eng
GR  - ES00267/ES/NIEHS NIH HHS/United States
GR  - ES07028/ES/NIEHS NIH HHS/United States
GR  - ES10196/ES/NIEHS NIH HHS/United States
PT  - Journal Article
PT  - Research Support, U.S. Gov't, P.H.S.
PL  - United States
TA  - Free Radic Biol Med
JT  - Free radical biology & medicine
JID - 8709159
RN  - 0 (Carbamates)
RN  - 0 (Catechols)
RN  - 0 (Oxidants)
RN  - 0 (Pesticides)
RN  - 0 (Reactive Oxygen Species)
RN  - LF3AJ089DQ (catechol)
RN  - S88TT14065 (Oxygen)
SB  - IM
MH  - Carbamates/*chemistry
MH  - Catalysis
MH  - Catechols/*chemistry
MH  - Oxidants/chemistry
MH  - Oxidation-Reduction
MH  - Oxidative Stress
MH  - Oxygen/chemistry
MH  - Pesticides/*chemistry
MH  - Reactive Oxygen Species/analysis/chemistry
MH  - Spectrophotometry, Ultraviolet
MH  - Structure-Activity Relationship
MH  - X-Ray Diffraction
EDAT- 2002/12/19 04:00
MHDA- 2004/01/30 05:00
CRDT- 2002/12/19 04:00
PHST- 2002/12/19 04:00 [pubmed]
PHST- 2004/01/30 05:00 [medline]
PHST- 2002/12/19 04:00 [entrez]
AID - S0891584902011693 [pii]
AID - 10.1016/s0891-5849(02)01169-3 [doi]
PST - ppublish
SO  - Free Radic Biol Med. 2002 Dec 15;33(12):1714-23. doi: 
      10.1016/s0891-5849(02)01169-3.