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Chemical Compound Review:

CHEMBL393474 N-(7H-purin-6-yl)hydroxylamine

Synonyms: CCRIS 2558, BIH6064, NSC-516286, KB-45842, LS-15073, ...

Kozmin, S.G. et al., Abdul-Masih, M.T. et al., Tsutsui, T. et al., Pavlov, Y.I. et al., Stepchenkova, E.I. et al., et al.

Stepchenkova, Kozmin, Alenin, Pavlov,

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Disease relevance of NSC 516286

We have shown previously that Escherichia coli and Salmonella enterica serovar Typhimurium strains carrying a deletion of the uvrB-bio region are hypersensitive to the mutagenic and toxic action of 6-hydroxylaminopurine (HAP) and related base analogs [1].

High impact information on NSC 516286

These results are consistent with (but do not prove) the hypothesis that the mechanism of 6-N-hydroxylaminopurine mutagenesis seen in both eucaryotic and procaryotic organisms is due to its conversion, in vivo, to a deoxynucleoside triphosphate which is incorporated ambiguously for dATP and dGTP during DNA replication [2].
Hypersensitivity of Escherichia coli Delta(uvrB-bio) mutants to 6-hydroxylaminopurine and other base analogs is due to a defect in molybdenum cofactor biosynthesis [1].
Mutagenic specificity of the base analog 6-N-hydroxylaminopurine in the LYS2 gene of yeast Saccharomyces cerevisiae [3].
The base analog 6-N-hydroxylaminopurine (HAP) mutagenesis is dependent on the integrity of the uvsE, uvsF and uvsB genes in Aspergillus nidulans [4].
HAM1, the gene controlling 6-N-hydroxylaminopurine sensitivity and mutagenesis in the yeast Saccharomyces cerevisiae [5].

Chemical compound and disease context of NSC 516286

The genetic activity of 2-amino-N6-hydroxyadenine or 2-amino-N-hydroxylaminopurine (AHA) and N6-hydroxyadenine or 6-N-hydroxylaminopurine (HAP) was studied in S. typhimurium, E. coli and Saccharomyces cerevisiae strains [6].

Biological context of NSC 516286

Genetic control of mutagenesis by the base analog 6-N-hydroxylaminopurine (HAP) was studied in a set of isogenic yeast strains carrying null or point mutations in DNA repair and replication genes [7].
6-N-hydroxylaminopurine (HAP)-induced accumulation of variability in haploid and diploid strains of Aspergillus nidulans [8].
BACKGROUND: N-hydroxylated base analogs, such as 6-hydroxylaminopurine (HAP) and 2-amino-6-hydroxylaminopurine (AHA), are strong mutagens in various organisms due to their ambiguous base-pairing properties [9].

Associations of NSC 516286 with other chemical compounds

2-Aminopurine is much less potent than 6-N-hydroxylaminopurine in inducing gene mutation in mammalian cells in culture and this corresponds to the relative activity of these two compounds in inducing tumors in rats and neoplastic transformation of Syrian hamster embryo cells in culture [10].

Gene context of NSC 516286

The enhancement in mutation induced by nitrous acid, UV light, and 6-N-hydroxylaminopurine has been confirmed in a forward-mutation assay (induction of mutations in the ADE1, ADE2 genes) [11].
Mutagenic specificity of the base analog 6-N-hydroxylaminopurine in the URA3 gene of the yeast Saccharomyces cerevisiae [12].

References

Hypersensitivity of Escherichia coli Delta(uvrB-bio) mutants to 6-hydroxylaminopurine and other base analogs is due to a defect in molybdenum cofactor biosynthesis. Kozmin, S.G., Pavlov, Y.I., Dunn, R.L., Schaaper, R.M. J. Bacteriol. (2000) [Pubmed]
Biochemical studies on the mutagen, 6-N-hydroxylaminopurine. Synthesis of the deoxynucleoside triphosphate and its incorporation into DNA in vitro. Abdul-Masih, M.T., Bessman, M.J. J. Biol. Chem. (1986) [Pubmed]
Mutagenic specificity of the base analog 6-N-hydroxylaminopurine in the LYS2 gene of yeast Saccharomyces cerevisiae. Kulikov, V.V., Derkatch, I.L., Noskov, V.N., Tarunina, O.V., Chernoff, Y.O., Rogozin, I.B., Pavlov, Y.I. Mutat. Res. (2001) [Pubmed]
The base analog 6-N-hydroxylaminopurine (HAP) mutagenesis is dependent on the integrity of the uvsE, uvsF and uvsB genes in Aspergillus nidulans. Babudri, N., Morpurgo, G., Marini, A., Prantera, G. Antonie Van Leeuwenhoek (1997) [Pubmed]
HAM1, the gene controlling 6-N-hydroxylaminopurine sensitivity and mutagenesis in the yeast Saccharomyces cerevisiae. Noskov, V.N., Staak, K., Shcherbakova, P.V., Kozmin, S.G., Negishi, K., Ono, B.C., Hayatsu, H., Pavlov, Y.I. Yeast (1996) [Pubmed]
The genetic activity of N6-hydroxyadenine and 2-amino-N6-hydroxyadenine in Escherichia coli, Salmonella typhimurium and Saccharomyces cerevisiae. Pavlov, Y.I., Noskov, V.N., Lange, E.K., Moiseeva, E.V., Pshenichnov, M.R., Khromov-Borisov, N.N. Mutat. Res. (1991) [Pubmed]
Base analog 6-N-hydroxylaminopurine mutagenesis in the yeast Saccharomyces cerevisiae is controlled by replicative DNA polymerases. Shcherbakova, P.V., Noskov, V.N., Pshenichnov, M.R., Pavlov, Y.I. Mutat. Res. (1996) [Pubmed]
6-N-hydroxylaminopurine (HAP)-induced accumulation of variability in haploid and diploid strains of Aspergillus nidulans. Pimpinelli, S., Marini, A., Babudri, N., Morpurgo, G. Curr. Genet. (1997) [Pubmed]
Genome-wide screening for genes whose deletions confer sensitivity to mutagenic purine base analogs in yeast. Stepchenkova, E.I., Kozmin, S.G., Alenin, V.V., Pavlov, Y.I. BMC Genet. (2005) [Pubmed]
Induction by modified purines (2-aminopurine and 6-N-hydroxylaminopurine) of chromosome aberrations and aneuploidy in Syrian hamster embryo cells. Tsutsui, T., Maizumi, H., Barrett, J.C. Mutat. Res. (1985) [Pubmed]
Saccharomyces cerevisiae mutants with enhanced induced mutation and altered mitotic gene conversion. Ivanov, E.L., Kovaltzova, S.V., Korolev, V.G. Mutat. Res. (1989) [Pubmed]
Mutagenic specificity of the base analog 6-N-hydroxylaminopurine in the URA3 gene of the yeast Saccharomyces cerevisiae. Shcherbakova, P.V., Pavlov, Y.I. Mutagenesis (1993) [Pubmed]

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