5-Methyl-2'-deoxycytidine | CAS# 838-07-3| Nucleosides

MedKoo Cat#: 122504 | Name: 5-Methyl-2'-deoxycytidine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

5-Methyl-2'-deoxycytidine is a nucleoside analogue that inhibits the synthesis of DNA.

Chemical Structure

5-Methyl-2'-deoxycytidine

CAS#838-07-3

Theoretical Analysis

MedKoo Cat#: 122504

Name: 5-Methyl-2'-deoxycytidine

CAS#: 838-07-3

Chemical Formula: C10H15N3O4

Exact Mass: 241.1063

Molecular Weight: 241.25

Elemental Analysis: C, 49.79; H, 6.27; N, 17.42; O, 26.53

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
2g	USD 350.00	2 Weeks
5g	USD 650.00	2 Weeks
10g	USD 950.00	2 Weeks

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Related CAS #

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Synonym

5-Methyl-2'-deoxycytidine; 838-07-3; 2'-Deoxy-5-methylcytidine; 5-Methyldeoxycytidine; CYTIDINE, 2'-DEOXY-5-METHYL-

IUPAC/Chemical Name

4-amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidin-2(1H)-one

InChi Key

LUCHPKXVUGJYGU-XLPZGREQSA-N

InChi Code

InChI=1S/C10H15N3O4/c1-5-3-13(10(16)12-9(5)11)8-2-6(15)7(4-14)17-8/h3,6-8,14-15H,2,4H2,1H3,(H2,11,12,16)/t6-,7+,8+/m0/s1

SMILES Code

OC[C@@H]1[C@H](C[C@H](N2C(N=C(C(C)=C2)N)=O)O1)O

Appearance

To be determined

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 241.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Giel-Pietraszuk M, Insińska-Rak M, Golczak A, Sikorski M, Barciszewska M, Barciszewski J. Quantification of 5-methyl-2'-deoxycytidine in the DNA. Acta Biochim Pol. 2015;62(2):281-6. doi: 10.18388/abp.2015_988. Epub 2015 Jun 22. PMID: 26098716. 2: Sato T. Structure of 5-methyl-2'-deoxycytidine. Acta Crystallogr C. 1988 May 15;44 ( Pt 5):870-2. doi: 10.1107/s0108270188000897. PMID: 3271083. 3: Shao J, Huang CH, Kalyanaraman B, Zhu BZ. Potent methyl oxidation of 5-methyl-2'-deoxycytidine by halogenated quinoid carcinogens and hydrogen peroxide via a metal-independent mechanism. Free Radic Biol Med. 2013 Jul;60:177-82. doi: 10.1016/j.freeradbiomed.2013.01.010. Epub 2013 Jan 30. PMID: 23376470; PMCID: PMC4476646. 4: Shilkin ES, Petrova DV, Poltorachenko VA, Boldinova EO, Zharkov DO, Makarova AV. [Template Properties of 5-Methyl-2'-Deoxycytidine and 5-Hydroxymethyl-2'-Deoxycytidine in Reactions with Human Translesion and Reparative DNA Polymerases]. Mol Biol (Mosk). 2021 Mar-Apr;55(2):305-311. Russian. doi: 10.31857/S0026898421020130. PMID: 33871443. 5: Kovatsi L, Fragou D, Samanidou V, Njau S, Kouidou S, Bailey A. Evaluation of 5-methyl-2'-deoxycytidine stability in hydrolyzed and nonhydrolyzed DNA by HPLC- UV. Bioanalysis. 2012 Feb;4(4):367-72. doi: 10.4155/bio.11.335. PMID: 22394137. 6: Liu S, Dunwell TL, Pfeifer GP, Dunwell JM, Ullah I, Wang Y. Detection of oxidation products of 5-methyl-2'-deoxycytidine in Arabidopsis DNA. PLoS One. 2013 Dec 31;8(12):e84620. doi: 10.1371/journal.pone.0084620. PMID: 24391970; PMCID: PMC3877350. 7: Shetlar MD, Chung J. The cyclobutane dimers of 2'-deoxyuridine, 2'-deoxycytidine, 5-methyl-2'-deoxycytidine and 5-bromo-2'-deoxyuridine. Photochem Photobiol. 2012 Sep-Oct;88(5):1236-47. doi: 10.1111/j.1751-1097.2012.01169.x. Epub 2012 Jun 6. PMID: 22571327. 8: Murata-Kamiya N, Kamiya H, Karino N, Ueno Y, Kaji H, Matsuda A, Kasai H. Formation of 5-formyl-2'-deoxycytidine from 5-methyl-2'-deoxycytidine in duplex DNA by Fenton-type reactions and gamma-irradiation. Nucleic Acids Res. 1999 Nov 15;27(22):4385-90. doi: 10.1093/nar/27.22.4385. PMID: 10536146; PMCID: PMC148720. 9: Celewicz L, Mayer M, Shetlar MD. The photochemistry of thymidylyl-(3'-5')-5-methyl-2'-deoxycytidine in aqueous solution. Photochem Photobiol. 2005 Mar-Apr;81(2):404-18. doi: 10.1562/2004-06-15-ra-201.1. PMID: 15493957. 10: Itoh K, Aida S, Ishiwata S, Yamaguchi T, Ishida N, Mizugaki M. Immunochemical detection of urinary 5-methyl-2'-deoxycytidine as a potential biologic marker for leukemia. Clin Chim Acta. 1995 Jan 31;234(1-2):37-45. doi: 10.1016/0009-8981(94)05986-3. PMID: 7758221. 11: Hu CW, Liu HH, Li YJ, Chao MR. Direct analysis of 5-methylcytosine and 5-methyl-2'-deoxycytidine in human urine by isotope dilution LC-MS/MS: correlations with N-methylated purines and oxidized DNA lesions. Chem Res Toxicol. 2012 Feb 20;25(2):462-70. doi: 10.1021/tx2004954. Epub 2012 Feb 8. PMID: 22268645. 12: Pan Y, Jing J, Yeung LWY, Sheng N, Zhang H, Yao B, Dai J. Associations of urinary 5-methyl-2'-deoxycytidine and 5-hydroxymethyl-2'-deoxycytidine with phthalate exposure and semen quality in 562 Chinese adult men. Environ Int. 2016 Sep;94:583-590. doi: 10.1016/j.envint.2016.06.020. Epub 2016 Jun 24. PMID: 27346742. 13: Jekunen A, Vilpo JA. 5-Methyl-2'-deoxycytidine. Metabolism and effects on cell lethality studied with human leukemic cells in vitro. Mol Pharmacol. 1984 May;25(3):431-5. PMID: 6587184. 14: Kaito C, Kai M, Higo T, Takayama E, Fukamachi H, Sekimizu K, Shiokawa K. Activation of the maternally preset program of apoptosis by microinjection of 5-aza-2'-deoxycytidine and 5-methyl-2'-deoxycytidine-5'-triphosphate in Xenopus laevis embryos. Dev Growth Differ. 2001 Aug;43(4):383-90. doi: 10.1046/j.1440-169x.2001.00579.x. PMID: 11473545. 15: Guo C, Xie C, Chen Q, Cao X, Guo M, Zheng S, Wang Y. A novel malic acid- enhanced method for the analysis of 5-methyl-2'-deoxycytidine, 5-hydroxymethyl-2'-deoxycytidine, 5-methylcytidine and 5-hydroxymethylcytidine in human urine using hydrophilic interaction liquid chromatography-tandem mass spectrometry. Anal Chim Acta. 2018 Nov 30;1034:110-118. doi: 10.1016/j.aca.2018.06.081. Epub 2018 Jul 3. PMID: 30193624; PMCID: PMC6162048. 16: Peña-Gómez MJ, Moreno-Gordillo P, Narmontė M, García-Calderón CB, Rukšėnaitė A, Klimašauskas S, Rosado IV. FANCD2 maintains replication fork stability during misincorporation of the DNA demethylation products 5-hydroxymethyl-2'-deoxycytidine and 5-hydroxymethyl-2'-deoxyuridine. Cell Death Dis. 2022 May 27;13(5):503. doi: 10.1038/s41419-022-04952-0. PMID: 35624090; PMCID: PMC9142498. 17: Nyce J. Gene silencing in mammalian cells by direct incorporation of electroporated 5-methyl-2'-deoxycytidine 5'-triphosphate. Somat Cell Mol Genet. 1991 Nov;17(6):543-50. doi: 10.1007/BF01233619. PMID: 1722592. 18: Celewicz L, Shetlar MD. The photochemistry of 5-methylcytosine and 5-methyl-2'-deoxycytidine in aqueous solution. Photochem Photobiol. 1992 Jun;55(6):823-30. doi: 10.1111/j.1751-1097.1992.tb08530.x. PMID: 1409889. 19: Ross BS, Han M, Ravikumar VT. Efficient large-scale synthesis of 5'-O-dimethoxytrityl-N4-benzoyl-5-methyl-2'-deoxycytidine. Nucleosides Nucleotides Nucleic Acids. 2006;25(7):765-70. doi: 10.1080/15257770600726059. PMID: 16898414.