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Identification of adducts formed in the reactions of 2′-deoxyguanosine and calf thymus DNA with glutaraldehyde

Glutaraldehyde (1,5‐pentanedial) is a widely used industrial chemical that has been found to be mutagenic in bacteria and mammalian cells. It has been claimed that glutaraldehyde forms adducts with 2′‐deoxyguanosine, 2′‐deoxyadenosine and 2′‐deoxycytidine, but until recently none of the adducts had been identified. In a very recent contribution from our laboratories, the structures were determined of three glutaraldehyde adducts formed in the reaction with 2′‐deoxyadenosine, and it was shown that one of the adducts is formed in calf thymus DNA. In the current work, we have studied the reaction of glutaraldehyde with 2′‐deoxyguanosine and calf thymus DNA in aqueous buffered solutions. Among the numerous adducts formed in the reaction with 2′‐deoxyguanosine, six compounds were found to be stable and could be isolated by semi‐preparative liquid chromatography and identified by UV absorbance and 1H and 13C NMR spectroscopic and mass spectrometric studies. Adduct dG350b, comprising two diastereomers, was found to be derived from one unit of glutaraldehyde which has been transformed to a tetrahydropyran ring so that C‐2 and C‐6 of the ring are attached to N‐1 and N2 of the purine unit resulting in a bridged structure. The adducts dG349a and b are analogous to dG350b, but the oxygen atom...

Olsen, Raymond; Backman, J; Molander, Pål; Klika, KD; Kronberg, L
European Journal of Organic Chemistry Wiley - VCH Verlag GmbH, European Journal of Organic Chemistry 2007(24): 4011–4018
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