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1 2007

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Identification of Adducts Formed in the Reaction of the Bacterial Mutagen 3-Chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone with Cytidine

Pluskota-Karwatka D., Munter T., Le Curieux F., Sjöholm R., Koroniak H., Kronberg L.

Polish Journal of Chemistry

2007

Vol. 81, nr 5-6

1145-1157

3-Chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone (CMCF), a strong bacterial mutagen reacts with cytidine in buffered aqueous solutions. The reaction products were separated by preparative HPLC C18 column chromatography and were structurally characterized by UV absorbance, 1H NMR and 13C NMR spectroscopy, and mass spectrometry. The main products were identified as 7-(-D-ribofuranosyl)-4-carboxy-6- oxo-6,7-dihydro-4H-pyrimido[1,6-alfa]pyrimidine-3-carbaldehyde (cM1FA-Cyd), and 7-(beta-D-ribofuranosyl)-6-oxo-6,7-dihydro-4H-pyrimido[1,6-alfa]pyrimidine-3-carbaldehyde (M1FA-Cyd). The highest yields of cM1FA-Cyd andM1FA-Cyd, being 12 and 1mol%respectively, were obtained in the reaction performed at pH 4.6 and 37 graduateC for 7 days. M1FA-Cyd and cM1FA-Cyd are structurally related to pfA-dR, the adduct previously identified in the reaction of 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone (MX) or 3-chloro-4-(chloromethyl)-5-hydroxy-2(5H)-furanone (CMCF) with 2'-deoxyadenosine.