5-Methyl-2'-deoxycytidine
(Synonyms: 5-甲基-2'-脱氧胞苷,5-Methyldeoxycytidine) 目录号 : GC42562
A pyrimidine nucleoside
Cas No.:838-07-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
5-Methyl-2'-deoxycytidine in single-stranded DNA can act in cis to signal de novo DNA methylation[1][2].
References:
[1]. Christman JK, et al. 5-Methyl-2'-deoxycytidine in single-stranded DNA can act in cis to signal de novo DNA methylation. Proc Natl Acad Sci U S A. 1995 Aug 1;92(16):7347-51.
[2]. Testillano PS, et al. The 5-methyl-deoxy-cytidine (5mdC) localization to reveal in situ the dynamics of DNA methylation chromatin pattern in a variety of plant organ and tissue cells during development. Physiol Plant. 2013 Sep;149(1):104-13.
| Cas No. | 838-07-3 | SDF | |
| 别名 | 5-甲基-2'-脱氧胞苷,5-Methyldeoxycytidine | ||
| Canonical SMILES | O=C(N=C(N)C(C)=C1)N1[C@H]2C[C@H](O)[C@@H](CO)O2 | ||
| 分子式 | C10H15N3O4 | 分子量 | 241.2 |
| 溶解度 | DMF: 5 mg/ml,DMSO: 20 mg/ml,PBS (pH 7.2): 10 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.1459 mL | 20.7297 mL | 41.4594 mL |
| 5 mM | 0.8292 mL | 4.1459 mL | 8.2919 mL |
| 10 mM | 0.4146 mL | 2.073 mL | 4.1459 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Quantification of 5-Methyl-2'-deoxycytidine in the DNA
Acta Biochim Pol 2015;62(2):281-6.PMID:26098716DOI:10.18388/abp.2015_988.
Methylation at position 5 of cytosine (Cyt) at the CpG sequences leading to formation of 5-methyl-cytosine (m(5)Cyt) is an important element of epigenetic regulation of gene expression. Modification of the normal methylation pattern, unique to each organism, leads to the development of pathological processes and diseases, including cancer. Therefore, quantification of the DNA methylation and analysis of changes in the methylation pattern is very important from a practical point of view and can be used for diagnostic purposes, as well as monitoring of the treatment progress. In this paper we present a new method for quantification of 5-methyl-2'deoxycytidine (m(5)C) in the DNA. The technique is based on conversion of m(5)C into fluorescent 3,N(4)-etheno-5-methyl-2'deoxycytidine (εm(5)C) and its identification by reversed-phase high-performance liquid chromatography (RP-HPLC). The assay was used to evaluate m(5)C concentration in DNA of calf thymus and peripheral blood of cows bred under different conditions. This approach can be applied for measuring of 5-methylcytosine in cellular DNA from different cells and tissues.
Structure of 5-Methyl-2'-deoxycytidine
Acta Crystallogr C 1988 May 15;44 ( Pt 5):870-2.PMID:3271083DOI:10.1107/s0108270188000897.
C10H15N3O4, Mr = 241.2, orthorhombic, P2(1)2(1)2(1), a = 10.454 (1), b = 11.922 (1), c = 9.057 (1) A, V = 1128.9 (1) A3, Z = 4, D chi = 1.419 Mg m-3, Cu K alpha radiation, lambda = 1.54178 A, mu = 0.95 mm-1, F(000) = 512, room temperature, R = 0.029 for 1186 observed reflections. The molecule has a typical C(2')-endo (2E) furanose ring associated with an anti base. The methyl substituent at C(5) causes a decrease of 2.6 degrees in the endocyclic bond angle at C(5). The ring oxygen O(4') is involved in an intermolecular hydrogen bond.
Evaluation of 5-Methyl-2'-deoxycytidine stability in hydrolyzed and nonhydrolyzed DNA by HPLC-UV
Bioanalysis 2012 Feb;4(4):367-72.PMID:22394137DOI:10.4155/bio.11.335.
Background: Although the determination of 5-Methyl-2'-deoxycytidine (5-MedC) in various biological samples is gaining increasing scientific interest, there are no data available regarding its stability. Results: We have currently evaluated the stability of 5-MedC and 2'-deoxycytidine (dC) at -20°C, both in hydrolyzed and nonhydrolyzed calf thymus DNA (CT DNA), as well as following repetitive freeze-thaw cycles. HPLC-UV was used for the accurate determination of the two 2'-deoxynucleosides. Statistical evaluation of the results revealed that 5-MedC and dC were stable in hydrolyzed CT DNA for at least 7 days and in nonhydrolyzed CT DNA for at least 65 days, when these were stored at -20°C. Furthermore, both 2'-deoxynucleosides were stable for at least three repetitive freeze-thaw cycles. Conclusion: By using HPLC-UV, we have evaluated the stability of 5-MedC and dC under storage conditions and repetitive freeze-thaw cycles. Our results are informative about the way samples should be handled and stored in epigenetic studies.
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.PMID:23376470DOI:10.1016/j.freeradbiomed.2013.01.010.
Halogenated quinones are a class of carcinogenic intermediates and are newly identified chlorination disinfection by-products in drinking water. We found recently that the highly reactive and biologically important hydroxyl radical ((•)OH) can be produced by halogenated quinones and H2O2 independent of transition metal ions. However, it is not clear whether these quinoid carcinogens and H2O2 can oxidize the nucleoside 5-Methyl-2'-deoxycytidine (5mdC) to its methyl oxidation products and, if so, what the underlying molecular mechanism is. Here we show that three methyl oxidation products, 5-(hydroperoxymethyl)-, 5-(hydroxymethyl)-, and 5-formyl-2'-deoxycytidine, could be produced when 5mdC was treated with tetrachloro-1,4-benzoquinone (TCBQ) and H2O2. The formation of the oxidation products was markedly inhibited by typical (•)OH scavengers and under anaerobic conditions. Analogous effects were observed with other halogenated quinones and the classic Fenton system. Based on these data, we propose that the oxidation of 5mdC by TCBQ/H2O2 might be through the following mechanism: (•)OH produced by TCBQ/H2O2 may first abstract hydrogen from the methyl group of 5mdC, leading to the formation of 5-(2'-deoxycytidylyl)methyl radical, which may combine with O2 to form the peroxyl radical. The unstable peroxyl radical transforms into the corresponding hydroperoxide 5-(hydroperoxymethyl)-2'-deoxycytidine, which reacts with TCBQ and results in the formation of 5-(hydroxymethyl)-2'-deoxycytidine and 5-formyl-2'-deoxycytidine. This is the first report that halogenated quinoid carcinogens and H2O2 can induce potent methyl oxidation of 5mdC via a metal-independent mechanism, which may partly explain their potential carcinogenicity.
Determination of 5-Methyl-2'-deoxycytidine in genomic DNA using high performance liquid chromatography-ultraviolet detection
J Chromatogr B Analyt Technol Biomed Life Sci 2009 Jul 1;877(20-21):1957-61.PMID:19501556DOI:10.1016/j.jchromb.2009.05.032.
The formation of 5-Methyl-2'-deoxycytidine (5-MedC) following methylation of the C-5 position of cytosine in genomic DNA provides an epigenetic mechanism for the regulation of gene expression and cellular differentiation. We describe the development of a method using HPLC-ultraviolet (UV) detection for the accurate determination of 5-MedC in DNA. Genomic DNA was obtained from HeLa cells and rat liver tissue using an optimised anion-exchange column DNA extraction procedure incorporating a ribonuclease incubation step to remove any potential interference from RNA. Following extraction the DNA samples were enzymatically hydrolysed to 2'-deoxynucleosides using a combination of an endo-exonuclease plus 5'-exonuclease together with a 3'-nucleotidase. The hydrolysed DNA samples (10 microg on column) were analysed using narrow-bore reverse phase HPLC-UV detection. The level of 5-MedC in the DNA samples was expressed as a percentage of the level of 2'-deoxycytidine (dC) determined from calibration lines constructed using authentic standards for 5-MedC and dC. The percentage 5-MedC level determined for commercially available calf thymus DNA was 6.26%, for HeLa cell DNA was 3.02% and for rat liver DNA was 3.55%.