Disease relevance of Oxirane-carboxaldehyde

• Novel activity of Escherichia coli mismatch uracil-DNA glycosylase (Mug) excising 8-(hydroxymethyl)-3,N4-ethenocytosine, a potential product resulting from glycidaldehyde reaction [1].
• 2-Chloroethanol and glycidaldehyde were negative in mouse lymphoma cells [2].
• Comparison of the mutagenic potency of 2-chloroethanol, 2-bromoethanol, 1,2-epoxybutane, epichlorohydrin and glycidaldehyde in Klebsiella pneumoniae, Drosophila melanogaster and L5178Y mouse lymphoma cells [2].

High impact information on Oxirane-carboxaldehyde

• Glycidaldehyde, a bifunctional carcinogenic alkylating agent, has been found to react with calf thymus DNA in vitro under alkaline conditions [3].
• At pH 10, however, this was a relatively minor product and the major adduct was 5,9-dihydro-7-(hydroxymethyl)-9- oxo-3-beta-D-deoxyribofuranosyl-3H-imidazo[1,2-a]purine-3'- monophosphate formed by the initial reaction of glycidaldehyde with deoxyguanosine residues [4].
• The alkylation frequency was 0.1-0.8 and 166 adducts/10(6) normal nucleotides for the treatment with bisphenol A diglycidylether and glycidaldehyde respectively [5].
• At low doses, however, the epoxide groups are hydrolysed before glycidaldehyde can be formed, unless the epoxide hydrolase is inhibited [6].
• The previously unreported glycidaldehyde adduct, 8-(hydroxymethyl)-3, N(4)-etheno-2'-deoxycytidine (8-HM-epsilondC), has been synthesized for the first time by reaction of 2'-deoxycytidine with bromoacetaldehyde at pH 4.5, followed by reduction with sodium borohydride [7].

Associations of Oxirane-carboxaldehyde with other chemical compounds

• The candidate mutagens methylglyoxal and glycidaldehyde are not detected as breakdown products of 3-chloro-2-hydroxypropanal at pH 7.4 and also have low mutagenic activity in TA100 [8].
• 3. The high activity of epoxide hydratase towards DGEBPA suggests that glyceraldehyde and not glycidaldehyde is formed in vivo [9].

Gene context of Oxirane-carboxaldehyde

• Alkylpurine-DNA-N-glycosylase excision of 7-(hydroxymethyl)-1,N6-ethenoadenine, a glycidaldehyde-derived DNA adduct [10].

Analytical, diagnostic and therapeutic context of Oxirane-carboxaldehyde

• The formation of DNA adducts in the skin of male C3H mice treated cutaneously with glycidaldehyde (2 or 10 mg/animal) in acetone has been investigated by HPLC coupled with fluorescence detection and 32P-postlabelling analysis [4].

References