PMID: 3768334Sep 9, 1986Paper

Synthesis and properties of oligodeoxyribonucleotides containing an ethylated internucleotide phosphate

Biochemistry
M Weinfeld, D C Livingston

Abstract

Internucleotide phosphotriesters comprise an important class of DNA lesions produced by carcinogenic alkylating agents. To avoid confusion resulting from the presence of other DNA lesions, synthetically prepared oligonucleotides containing ethylated internucleotide phosphates as the sole form of damage were employed to investigate several chemical and biochemical properties of DNA alkyl phosphotriesters. A total of four oligonucleotides were synthesised for this study, the dimers Tp(Et)T and pTp(Et)T and the decamer d-TpTpTp(Et)TpCpTpApTpTpT together with its unmodified analogue. The dimers were characterized by UV and phosphorus NMR spectroscopy and the decamers by two-dimensional homochromatography, alkali hydrolysis, and variable-temperature circular dichroism (CD). Alkali hydrolysis of the ethylated decamer produced strand breaks in approximately 75% of the molecules. This is in close agreement with data previously obtained for dinucleoside ethyl phosphotriesters and triesters in alkylated cellular DNA. Results from the CD study suggest that the ethyl substituent does not disrupt base stacking within the oligomer. The interactions of two enzymes with the alkylated oligonucleotides were examined. First, it was found that eth...Continue Reading

References

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Citations

Nov 19, 2009·Mutagenesis·George D D JonesPeter B Farmer
Sep 18, 2008·Nucleic Acids Research·Alexandre V LebedevGerald Zon
Sep 12, 2009·Current Protocols in Nucleic Acid Chemistry·Alexandre Lebedev

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