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Chemical Compound Review:

SureCN20268 4-amino-1-[(2R,4S,5R)-4- hydroxy-5...

Synonyms: AG-H-34493, CHEBI:47876, ANW-37726, AC-13962, AK-72796, ...

Itoh, K. et al., Song, L. et al., Lacroix, L. et al., Friso, S. et al., Morey, S.R. et al., et al.

Song, James, Kazim, Karpf, Friso, Girelli, Trabetti, Olivieri, Guarini, Pignatti, Corrocher, Choi, Friso, Choi, Dolnikowski, Selhub,

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

High impact information on 838-07-3

5-Methyl-2'-deoxycytidine in single-stranded DNA can act in cis to signal de novo DNA methylation [1].
We analyzed DNA methylation in TRAMP and found that global levels of 5-methyl-2'-deoxycytidine are unaltered, whereas specific tumors display centromeric repeat hypomethylation [2].
Importantly, both RNA contamination and incomplete DNA hydrolysis had no appreciable effect on 5-methyl-2'-deoxycytidine quantification [3].
LC separation of 5-methyl-2'-deoxycytidine from the four deoxyribonucleosides, the four ribonucleosides, and 5-methyl-2'-cytidine, a RNA methylation product, has been achieved within 15 min [3].
Carriers of the 1298AA wild-type genotype showed lower genomic DNA methylation compared with 1298AC or 1298CC genotypes [3.72 versus 8.59 or 6.79 ng 5-methyl-2'-deoxycytidine (5-mCyt)/microg DNA, P < 0.0001 and P = 0.007, respectively] [4].

Biological context of 838-07-3

Gene silencing in mammalian cells by direct incorporation of electroporated 5-methyl-2'-deoxycytidine 5'-triphosphate [5].

Anatomical context of 838-07-3

Preparation of a monoclonal antibody specific for 5-methyl-2'-deoxycytidine and its application for the detection of DNA methylation levels in human peripheral blood cells [6].

Associations of 838-07-3 with other chemical compounds

The photochemistry of 5-methylcytosine and 5-methyl-2'-deoxycytidine in aqueous solution [7].
AMC had the highest reactivity to 5-methyl-2'-deoxycytidine among reactive compounds and had no or very slight cross-reactivity to cytidine-related compounds and any other compounds [8].

Gene context of 838-07-3

Then the inhibition ELISA system using AMC was established and urinary levels of 5-methyl-2'-deoxycytidine in healthy individuals and cancer patients were determined [8].

Analytical, diagnostic and therapeutic context of 838-07-3

We developed a method for quantitative determination of 5-methyl-2'-deoxycytidine in human DNA using liquid chromatography/electrospray ionization mass spectrometry (LC/ESI-MS) [9].
Those containing 5-(1-propynyl)-2'-deoxyuridine (pdU) and 5-methyl-2'-deoxycytidine (5meC) showed superior binding characteristics at neutral pH and at low magnesium concentrations, as determined by gel mobility shift assays and thermal dissociation profiles [10].
Time-resolved fluoroimmunoassay of 5-methyl-2'-deoxycytidine [11].
Electrospray ionization mass spectrometry of 5-methyl-2'-deoxycytidine and its determination in urine by liquid chromatography/electrospray ionization tandem mass spectrometry [12].
Radioimmunoassay of 5-methyl-2'-deoxycytidine. A method for the quantitation of DNA methylation [13].

References

5-Methyl-2'-deoxycytidine in single-stranded DNA can act in cis to signal de novo DNA methylation. Christman, J.K., Sheikhnejad, G., Marasco, C.J., Sufrin, J.R. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
DNA methylation pathway alterations in an autochthonous murine model of prostate cancer. Morey, S.R., Smiraglia, D.J., James, S.R., Yu, J., Moser, M.T., Foster, B.A., Karpf, A.R. Cancer Res. (2006) [Pubmed]
Specific method for the determination of genomic DNA methylation by liquid chromatography-electrospray ionization tandem mass spectrometry. Song, L., James, S.R., Kazim, L., Karpf, A.R. Anal. Chem. (2005) [Pubmed]
The MTHFR 1298A>C polymorphism and genomic DNA methylation in human lymphocytes. Friso, S., Girelli, D., Trabetti, E., Olivieri, O., Guarini, P., Pignatti, P.F., Corrocher, R., Choi, S.W. Cancer Epidemiol. Biomarkers Prev. (2005) [Pubmed]
Gene silencing in mammalian cells by direct incorporation of electroporated 5-methyl-2'-deoxycytidine 5'-triphosphate. Nyce, J. Somat. Cell Mol. Genet. (1991) [Pubmed]
Preparation of a monoclonal antibody specific for 5-methyl-2'-deoxycytidine and its application for the detection of DNA methylation levels in human peripheral blood cells. Mizugaki, M., Itoh, K., Yamaguchi, T., Ishiwata, S., Hishinuma, T., Nozaki, S., Ishida, N. Biol. Pharm. Bull. (1996) [Pubmed]
The photochemistry of 5-methylcytosine and 5-methyl-2'-deoxycytidine in aqueous solution. Celewicz, L., Shetlar, M.D. Photochem. Photobiol. (1992) [Pubmed]
Immunochemical detection of urinary 5-methyl-2'-deoxycytidine as a potential biologic marker for leukemia. Itoh, K., Aida, S., Ishiwata, S., Yamaguchi, T., Ishida, N., Mizugaki, M. Clin. Chim. Acta (1995) [Pubmed]
A method to assess genomic DNA methylation using high-performance liquid chromatography/electrospray ionization mass spectrometry. Friso, S., Choi, S.W., Dolnikowski, G.G., Selhub, J. Anal. Chem. (2002) [Pubmed]
Triplex formation by oligonucleotides containing 5-(1-propynyl)-2'-deoxyuridine: decreased magnesium dependence and improved intracellular gene targeting. Lacroix, L., Lacoste, J., Reddoch, J.F., Mergny, J.L., Levy, D.D., Seidman, M.M., Matteucci, M.D., Glazer, P.M. Biochemistry (1999) [Pubmed]
Time-resolved fluoroimmunoassay of 5-methyl-2'-deoxycytidine. Vilpo, J.A., Rasi, S., Suvanto, E., Vilpo, L.M. Anal. Biochem. (1986) [Pubmed]
Electrospray ionization mass spectrometry of 5-methyl-2'-deoxycytidine and its determination in urine by liquid chromatography/electrospray ionization tandem mass spectrometry. Zambonin, C.G., Palmisano, F. Rapid Commun. Mass Spectrom. (1999) [Pubmed]
Radioimmunoassay of 5-methyl-2'-deoxycytidine. A method for the quantitation of DNA methylation. Vilpo, J.A., Rasi, S., Vilpo, L.M. J. Immunol. Methods (1984) [Pubmed]

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