Studies on the Nucleotide Arrangement in Deoxyribonucleic Acids. XI. Selective Removal of Cytosine as a Tool for the Study of the Nucleotide Arrangement in Deoxyribonucleic Acid<sup>*</sup>

Shapiro, Herman S.; Chargaff, Erwin

doi:10.1021/bi00873a034

Cited by 34 publications

(3 citation statements)

References 25 publications

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“…Deamination products of cytosine and adenine may be repaired (29,30), but the extreme instability of xanthine in DNA (31) leads to its rapid depurination (32). The rate of deamination of guanine may normally be so slow, and the half-life of xanthine may be so short that no excision repair system evolved.…”

Section: Resultsmentioning

confidence: 99%

DNA damage and mutation in human cells exposed to nitric oxide in vitro.

Nguyen

Brunson²,

Crespi³

et al. 1992

Proc. Natl. Acad. Sci. U.S.A.

880

426

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Nitric oxide (NO') is a physiological messenger formed by several cell types. Reaction with 02 forms oxides that nitrosate amines at pH values near 7. We now report experiments in which NO' was added to intact human cells and to aerobic solutions of DNA, RNA, guanine, or adenine. TK6 human lymphoblastoid cells were mutated 15-to 18-fold above background levels at both the HPRT and TK gene loci. Xan-

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Section: Resultsmentioning

confidence: 99%

DNA damage and mutation in human cells exposed to nitric oxide in vitro.

Nguyen

Brunson²,

Crespi³

et al. 1992

Proc. Natl. Acad. Sci. U.S.A.

880

426

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“…For this reason, it is not possible to determine the rate of adenine deamination in double-stranded DNA by prolonged incubation of DNA solutions at temperatures below the fm, because significant depurination with accompanying chain breakage and generation of single-stranded sequences would occur before detectable amounts of hypoxanthine were formed. Since a hypoxanthine-deoxyribose bond is slightly weaker than an adenine-deoxyribose bond in DNA (Shapiro & Chargaff, 1966), some of the deaminated adenine residues were released from the DNA by depurination during the longest incubations. In the standard procedure, the whole DNA solution was analyzed for the presence of hypoxanthine after heat treatment.…”

Section: Resultsmentioning

confidence: 99%

Hypoxanthine in deoxyribonucleic acid: generation by heat-induced hydrolysis of adenine residues and release in free form by a deoxyribonucleic acid glycosylase from calf thymus

Karran¹,

Lindahl²

1980

Biochemistry

168

110

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A slow conversion of adenine residues to hypoxanthine occurs in single-stranded DNA when heated in neutral aqueous buffers. The rate of this reaction at pH 7.6 and 110 degrees C is k = 4 x 10(-8) s-1, as determined by base analysis of heat-treated DNA that contains radioactively labeled adenine residues. It is proposed that adenine deamination is one of several forms of hydrolytic damage that may occur as spontaneous premutagenic lesions in DNA in vivo. Cell extracts from calf thymus and human fibroblasts contain a DNA glycosylase activity with specifically catalyzes the release of free hypoxanthine from DNA or polydeoxyribonucleotides that contain dIMP residues. Several properties of the purified enzyme from calf thymus are described: It has an approximate molecular weight of 31 000. No cofactors are required for activity. The enzymatic release of hypoxanthine occurs readily from double-stranded polydeoxyribonucleotides that have either thymine or cytosine residues in the complementary strand. Single-stranded polymers are 10-20-fold more slowly attacked, and there is no detectable cleavage of monomeric dIMP. Hypoxanthine is liberated from DNA directly as a free base. Thus, when poly(dI) x poly(dC) containing both [3H]-dIMP and [32P]dIMP residues was employed as the substrate, 3H-labeled hypoxanthine but no 32P-labeled material was released in ethanol-soluble form. The hypoxanthine-DNA glycosylase presumably acts in DNA repair by preventing deaminated adenine residues from being expressed as mu.

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“…Deoxyinosine can be generated in DNA from deoxyadenosine by deamination either spontaneously or in the presence of nitrous acid. 5) Point mutations are thought to be induced in many cases by modification of a base in DNA by a mutagen and subsequent misincorporation of an incorrect deoxynucleoside triphosphate at the site opposite to the modified base catalyzed by DNA polymerase. The base pairing properties of hypoxanthine had been studied, and results had shown that hypoxanthine in oligonucleotides forms a stable base pair with an adenine or cytosine residue in the opposite strand.…”

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confidence: 99%

Non-canonical hydrogen bonds in genetic information flow

Ohtsuka

2005

Proceedings of the Japan Academy. Ser. B: Physical and Biologic

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Non-Watson-Crick-type hydrogen bonds involving minor nucleosides such as inosine in anticodon loops of transfer RNA are found in nucleic acids. Inosine contains hypoxanthine as a nucleobase and can form base pairs with various bases in the genetic decoding process. This property was applied to cloning complementary DNA by using oligodeoxyribonucleotide primers which contain deoxyinosine residues. Hypoxanthine is generated by deamination of adenine, one of the major nucleobases in DNA and RNA. Formation of unusual hydrogen bonds derived from damaged nucleobases in nucleic acids is thought to be main cause of disorders in genetic information flow. Mutagenesis and carcinogenesis of damaged bases, including hypoxanthine, 7, 8-dihydro-8-oxoguanine (8-oxoguanine) and pyrimidine photo-dimers in c-Haras genes, were investigated by using synthetic genes containing modified nucleotides. The mode of recognition of unusual base pairing between a thymine photo-dimer and adenine by a repair enzyme was studied by X-ray analysis.

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Studies on the Nucleotide Arrangement in Deoxyribonucleic Acids. XI. Selective Removal of Cytosine as a Tool for the Study of the Nucleotide Arrangement in Deoxyribonucleic Acid^*

Abstract: When calf thymus deoxyribonucleic acid (DNA) is treated with nitrous acid at pH 3.35, com-

Cited by 34 publications

References 25 publications

DNA damage and mutation in human cells exposed to nitric oxide in vitro.

DNA damage and mutation in human cells exposed to nitric oxide in vitro.

Hypoxanthine in deoxyribonucleic acid: generation by heat-induced hydrolysis of adenine residues and release in free form by a deoxyribonucleic acid glycosylase from calf thymus

Non-canonical hydrogen bonds in genetic information flow

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Studies on the Nucleotide Arrangement in Deoxyribonucleic Acids. XI. Selective Removal of Cytosine as a Tool for the Study of the Nucleotide Arrangement in Deoxyribonucleic Acid*

Abstract: When calf thymus deoxyribonucleic acid (DNA) is treated with nitrous acid at pH 3.35, com-

Cited by 34 publications

References 25 publications

DNA damage and mutation in human cells exposed to nitric oxide in vitro.

DNA damage and mutation in human cells exposed to nitric oxide in vitro.

Hypoxanthine in deoxyribonucleic acid: generation by heat-induced hydrolysis of adenine residues and release in free form by a deoxyribonucleic acid glycosylase from calf thymus

Non-canonical hydrogen bonds in genetic information flow

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About

Studies on the Nucleotide Arrangement in Deoxyribonucleic Acids. XI. Selective Removal of Cytosine as a Tool for the Study of the Nucleotide Arrangement in Deoxyribonucleic Acid^*