chloroacetaldehyde (CAA)


OTHER NAMES:
toxic metabolites of vinyl chloride


ABBREVIATIONS:
CAA


DESCRIPTION: 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.

Chloroacetaldehyde reacts with unpaired cytosine and adenine nucleobases in DNA producing 3,N4-ethenocytosine (εC) and 1,N6-ethenoadenine (εA), respectively (Fig.1).

DNA DAMAGES:
1,N6-etheno-A in (1εA) dsDNA
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)
1,N2-etheno-G (εG) in ssDNA
1,N6-etheno-A (1εA) in ssDNA
N2,3-etheno-G (N2,3-εG)
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)
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
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)
3,N4-ethenoC (εC) in ssDNA ALKBH2 C→A transversion
mutagenesis
point mutation
substitution
transversion
direct reversal (DR)

References:

  • Chemical mapping of cytosines enzymatically flipped out of the DNA helix.
    Daujotyte D., Liutkeviciūte Z., Tamulaitis G., Klimasauskas S.
    Nucleic Acids Res., 2008 Jun, 36:e57 [PUBMED]

Last modification date: Aug. 20, 2011