Evidence in Escherichia coli that N3-methyladenine lesions induced by a minor groove binding methyl sulfonate ester can be processed by both base and nucleotide excision repair

Biochemistry
D ShahB Gold

Abstract

It has been previously reported that a neutral DNA equilibrium binding agent based on an N-methylpyrrolecarboxamide dipeptide (lex) and modified with an O-methyl sulfonate ester functionality (MeOSO(2)-lex) selectively affords N3-methyladenine lesions. To study the interaction of the neutral lex dipeptide with calf thymus DNA, we have prepared stable, nonmethylating sulfone analogues of MeOSO(2)-lex that are neutral and cationic. Thermodynamic studies show that both the neutral and monocationic sulfone compounds bind to DNA with K(b)'s of 10(5) in primarily entropy-driven reactions. To determine how the cytotoxic N3-methyladenine adduct generated from MeOSO(2)-lex is repaired in E. coli, MeOSO(2)-lex was tested for toxicity in wild-type E. coli and in mutant strains defective in base excision repair (tag and/or alkA glycosylases or apn endonuclease), nucleotide excision repair (uvrA), and both base and nucleotide excision repair (tag/alkA/uvrA). The results clearly demonstrate the cellular toxicity of the N3-methyladenine lesion, and the protective role of base excision glycosylase proteins. A novel finding is that in the absence of functional base excision glycosylases, nucleotide excision repair can also protect cells from th...Continue Reading

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Citations

Dec 14, 2012·Chemical Research in Toxicology·Prema IyerBarry Gold
Oct 31, 2009·Carcinogenesis·Nidhi ShrivastavJohn M Essigmann
May 26, 2015·Journal of Ophthalmic & Vision Research·Mohammad Mehdi SadoughiSepehr Feizi
Jan 27, 2004·Journal of Cellular Biochemistry·Gilberto Fronza, Barry Gold
Nov 13, 2010·Toxicological Sciences : an Official Journal of the Society of Toxicology·Zoulikha M ZaïrGeorge E Johnson
Mar 26, 2004·Nature Reviews. Molecular Cell Biology·Barbara Sedgwick
Oct 12, 2010·Journal of Nucleic Acids·Samuel SettlesBarry Gold
Aug 21, 2021·Journal of Medicinal Chemistry·Leah L LowderSridhar Varadarajan
Oct 31, 2009·Mutation Research·Paola MontiGilberto Fronza

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