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5-Methylcytosine Sale

(Synonyms: 5-甲基胞嘧啶) 目录号 : GC35166

5-Methylcytosine, a methylated form of the DNA base cytosine, is a major epigenetic mark in the nuclear DNA in mammals and may be involved in the regulation of gene transcription.

5-Methylcytosine Chemical Structure

Cas No.:554-01-8

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产品描述

5-Methylcytosine, a methylated form of the DNA base cytosine, is a major epigenetic mark in the nuclear DNA in mammals and may be involved in the regulation of gene transcription.

Chemical Properties

Cas No. 554-01-8 SDF
别名 5-甲基胞嘧啶
Canonical SMILES O=C1N=CC(C)=C(N)N1
分子式 C5H7N3O 分子量 125.13
溶解度 DMSO: 8.33 mg/mL (66.57 mM); Water: 7.14 mg/mL (57.06 mM) 储存条件 Store at RT
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1 mM 7.9917 mL 39.9584 mL 79.9169 mL
5 mM 1.5983 mL 7.9917 mL 15.9834 mL
10 mM 0.7992 mL 3.9958 mL 7.9917 mL
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Research Update

Bisulfite-free direct detection of 5-Methylcytosine and 5-hydroxymethylcytosine at base resolution

Nat Biotechnol 2019 Apr;37(4):424-429.PMID:30804537DOI:10.1038/s41587-019-0041-2.

Bisulfite sequencing has been the gold standard for mapping DNA modifications including 5-Methylcytosine (5mC) and 5-hydroxymethylcytosine (5hmC) for decades1-4. However, this harsh chemical treatment degrades the majority of the DNA and generates sequencing libraries with low complexity2,5,6. Here, we present a bisulfite-free and base-level-resolution sequencing method, TET-assisted pyridine borane sequencing (TAPS), for detection of 5mC and 5hmC. TAPS combines ten-eleven translocation (TET) oxidation of 5mC and 5hmC to 5-carboxylcytosine (5caC) with pyridine borane reduction of 5caC to dihydrouracil (DHU). Subsequent PCR converts DHU to thymine, enabling a C-to-T transition of 5mC and 5hmC. TAPS detects modifications directly with high sensitivity and specificity, without affecting unmodified cytosines. This method is nondestructive, preserving DNA fragments over 10 kilobases long. We applied TAPS to the whole-genome mapping of 5mC and 5hmC in mouse embryonic stem cells and show that, compared with bisulfite sequencing, TAPS results in higher mapping rates, more even coverage and lower sequencing costs, thus enabling higher quality, more comprehensive and cheaper methylome analyses.

5-Methylcytosine and its derivatives

Adv Clin Chem 2014;67:151-87.PMID:25735861DOI:10.1016/bs.acc.2014.09.003.

Epigenetics has undergone an explosion in the past decade. DNA methylation, consisting of the addition of a methyl group at the fifth position of cytosine (5-Methylcytosine, 5-mC) in a CpG dinucleotide, is a well-recognized epigenetic mark with important functions in cellular development and pathogenesis. Numerous studies have focused on the characterization of DNA methylation marks associated with disease development as they may serve as useful biomarkers for diagnosis, prognosis, and prediction of response to therapy. Recently, novel cytosine modifications with potential regulatory roles such as 5-hydroxymethylcytosine (5-hmC), 5-formylcytosine (5-foC), and 5-carboxylcytosine (5-caC) have been discovered. Study of the functions of 5-mC and its oxidation derivatives promotes the understanding of the mechanism underlying association of epigenetic modifications with disease biology. In this respect, much has been accomplished in the development of methods for the discovery, detection, and location analysis of 5-mC and its oxidation derivatives. In this review, we focus on the recent advances for the global detection and location study of 5-mC and its oxidation derivatives 5-hmC, 5-foC, and 5-caC.

RNA 5-Methylcytosine modification and its emerging role as an epitranscriptomic mark

RNA Biol 2021 Oct 15;18(sup1):117-127.PMID:34288807DOI:10.1080/15476286.2021.1950993.

5-Methylcytosine (m5C) is identified as an abundant and conserved modification in various RNAs, including tRNAs, mRNAs, rRNAs, and other non-coding RNAs. The application of high-throughput sequencing and mass spectrometry allowed for the detection of m5C at a single-nucleotide resolution and at a global abundance separately; this contributes to a better understanding of m5C modification and its biological functions. m5C modification plays critical roles in diverse aspects of RNA processing, including tRNA stability, rRNA assembly, and mRNA translation. Notably, altered m5C modifications and mutated RNA m5C methyltransferases are associated with diverse pathological processes, such as nervous system disorders and cancers. This review may provide new sights of molecular mechanism and functional importance of m5C modification.

The role of RNA m5C modification in cancer metastasis

Int J Biol Sci 2021 Aug 2;17(13):3369-3380.PMID:34512153DOI:10.7150/ijbs.61439.

Epigenetic modification plays a crucial regulatory role in the biological processes of eukaryotic cells. The recent characterization of DNA and RNA methylation is still ongoing. Tumor metastasis has long been an unconquerable feature in the fight against cancer. As an inevitable component of the epigenetic regulatory network, 5-Methylcytosine is associated with multifarious cellular processes and systemic diseases, including cell migration and cancer metastasis. Recently, gratifying progress has been achieved in determining the molecular interactions between m5C writers (DNMTs and NSUNs), demethylases (TETs), readers (YTHDF2, ALYREF and YBX1) and RNAs. However, the underlying mechanism of RNA m5C methylation in cell mobility and metastasis remains unclear. The functions of m5C writers and readers are believed to regulate gene expression at the post-transcription level and are involved in cellular metabolism and movement. In this review, we emphatically summarize the recent updates on m5C components and related regulatory networks. The content will be focused on writers and readers of the RNA m5C modification and potential mechanisms in diseases. We will discuss relevant upstream and downstream interacting molecules and their associations with cell migration and metastasis.

The Roles of Host 5-Methylcytosine RNA Methyltransferases during Viral Infections

Int J Mol Sci 2020 Oct 31;21(21):8176.PMID:33142933DOI:10.3390/ijms21218176.

Eukaryotic 5-Methylcytosine RNA methyltransferases catalyze the transfer of a methyl group to the fifth carbon of a cytosine base in RNA sequences to produce 5-Methylcytosine (m5C). m5C RNA methyltransferases play a crucial role in the maintenance of functionality and stability of RNA. Viruses have developed a number of strategies to suppress host innate immunity and ensure efficient transcription and translation for the replication of new virions. One such viral strategy is to use host m5C RNA methyltransferases to modify viral RNA and thus to affect antiviral host responses. Here, we summarize the latest findings concerning the roles of m5C RNA methyltransferases, namely, NOL1/NOP2/SUN domain (NSUN) proteins and DNA methyltransferase 2/tRNA methyltransferase 1 (DNMT2/TRDMT1) during viral infections. Moreover, the use of m5C RNA methyltransferase inhibitors as an antiviral therapy is discussed.