vinyl chloride metabolites


OTHER NAMES:
vinyl chloride
toxic metabolites of vinyl chloride


DESCRIPTION: Vinyl chloride is mainly transformed in the liver.

Vinyl chloride is first metabolised to chloroethylene oxide. This unstable epoxide is then transformed into chloroacetaldehyde which is further converted to chloroethanol or monochloroacetic acid. Chloroethylene oxide, chloroacetaldehyde and monochloroacetic acid are the main toxic metabolites of vinyl chloride.


Vinyl chloride is a flammable and colorless gas with a mildly sweet odor. It can be formed when other substances such as trichloroethane and trichloroethylene are broken down. It is used to make polyvinyl chloride (PVC) plastic and vinyl products. Exposure to vinyl chloride occurs mainly in the workplace. 
Acute exposure to high levels of vinyl chloride in air has resulted in central nervous system effects in humans. Chronic exposure to vinyl chloride through inhalation and oral exposure in humans has resulted in liver damage. Vinyl chloride exposure has been shown to increase the risk of a rare form of liver cancer in humans.

Vinyl chloride is mainly transformed in the liver via the mixed function oxidase system. The alcohol dehydrogenase system and the catalase system may also be involved. Vinyl chloride is first metabolised to chloroethylene oxide, then it is transformed into chloroacetaldehyde, which is further converted to chloroethanol or monochloroacetic acid. Chloroethylene oxide, chloroacetaldehyde and monochloroacetic acid are the main toxic metabolites of vinyl chloride.

Chronis exposure of humans via inhalation and oral exposure may cause liver damage. Central nervous system effects (such as dizziness, drowsiness, fatigue, headache, memory loss) and peripheral nervous system effects (such as peripheral neuropathy, tingling, numbness, weakness and pain in fingers) have been reported by humans exposed to vinyl chloride in the workplace.

DNA DAMAGES:
1,N6-etheno-A in (1εA) dsDNA
3,N4-ethano-C (EC)
1,N2-etheno-G (1,2εG) in dsDNA
3,N4-etheno-C (εC) in dsDNA
1,N6-etheno-A (1εA)
1,N6-alpha-hydroxyethano-A (HEA)
Fapy-7meG from Fapy-7meG:C
1,N2-etheno-G (εG) in ssDNA
1,N6-etheno-A (1εA) in ssDNA
N2,3-etheno-G (N2,3-εG)
OEG
FapyG from FapyG:C
3,N4-ethenoC (εC) in ssDNA


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NAME STRUCTURE PROTEINS DNA DAMAGE EFFECT(S) PATHWAY(S) RELATED
1,N6-etheno-A in (1εA) dsDNA AlkA
Fpg (MutM)
ANPG (MPG)
AlkB
mutagenesis
point mutation
substitution
transition
transversion
base excision repair (BER)
direct reversal (DR)
3,N4-ethano-C (EC) AlkA mutagenesis
point mutation
substitution
base excision repair (BER)
1,N2-etheno-G (1,2εG) in dsDNA Mug
ANPG (MPG)
Mug
-1 frameshift
deletion
G→C transversion
G→T transversion
mutagenesis
point mutation
stalled replication fork
transversion
base excision repair (BER)
3,N4-etheno-C (εC) in dsDNA Mug
TDG
AlkB
SMUG1
C→A transversion
mutagenesis
point mutation
substitution
transversion
base excision repair (BER)
direct reversal (DR)
1,N6-etheno-A (1εA) AlkA
Fpg (MutM)
ANPG (MPG)
AlkB
ALKBH2
A→T transversion
mutagenesis
point mutation
transversion
base excision repair (BER)
direct reversal (DR)
1,N6-alpha-hydroxyethano-A (HEA) cell cycle arrest
DNA backbone distortion
mutagenesis
stalled replication fork
Fapy-7meG from Fapy-7meG:C hOGG1 mutagenesis
point mutation
stalled replication fork
substitution
base excision repair (BER)
1,N2-etheno-G (εG) in ssDNA ALKBH2 deletion
G→C transversion
G→T transversion
mutagenesis
point mutation
stalled replication fork
substitution
transversion
direct reversal (DR)
1,N6-etheno-A (1εA) in ssDNA ALKBH2 mutagenesis
point mutation
transition
transversion
direct reversal (DR)
N2,3-etheno-G (N2,3-εG) AlkA G→A transition
mutagenesis
point mutation
substitution
transition
base excision repair (BER)
OEG UvrC
UvrB
no mutagenesis nucleotide excision repair (NER)
prokaryotic (SOS) response
FapyG from FapyG:C hOGG1 mutagenesis
point mutation
stalled replication fork
substitution
base excision repair (BER)
3,N4-ethenoC (εC) in ssDNA ALKBH2 C→A transversion
mutagenesis
point mutation
substitution
transversion
direct reversal (DR)

Last modification date: Aug. 13, 2011