5-Methyluridine
(Synonyms: 5-甲基尿苷) 目录号 : GC33514
A pyrimidine nucleoside
Cas No.:1463-10-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
5-Methyluridine is a pyrimidine nucleoside and methylated form of uridine .1 It enhances the antitumor activity of 5-fluorouracil in a mouse Erlich solid carcinoma model and a P388 murine leukemia model. It has been used to characterize the activity of a variety of enzymes, including uridine nucleosidase.2
1.Tezuka, M., Chiba, Y., Okada, S., et al.Enhancement of antitumor activity of 5-fluorouracil by ribothymidineJ. Pharmacobiodyn.9(8)683-687(1986) 2.Magni, G., Fioretti, E., Ipata, P.L., et al.Bakers' yeast uridine nucleosidase. Purification, composition, and physical and enzymatic propertiesJ. Biol. Chem.250(1)9-13(1975)
| Cas No. | 1463-10-1 | SDF | |
| 别名 | 5-甲基尿苷 | ||
| Canonical SMILES | OC[C@@H]1[C@H]([C@H]([C@H](N2C(NC(C(C)=C2)=O)=O)O1)O)O | ||
| 分子式 | C10H14N2O6 | 分子量 | 258.23 |
| 溶解度 | DMSO: ≥ 100 mg/mL (387.25 mM); Water: 100 mg/mL (387.25 mM) | 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 | 3.8725 mL | 19.3626 mL | 38.7252 mL |
| 5 mM | 0.7745 mL | 3.8725 mL | 7.745 mL |
| 10 mM | 0.3873 mL | 1.9363 mL | 3.8725 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。
RNADSN: Transfer-Learning 5-Methyluridine (m5U) Modification on mRNAs from Common Features of tRNA
Int J Mol Sci 2022 Nov 4;23(21):13493.PMID:36362279DOI:10.3390/ijms232113493.
One of the most abundant non-canonical bases widely occurring on various RNA molecules is 5-Methyluridine (m5U). Recent studies have revealed its influences on the development of breast cancer, systemic lupus erythematosus, and the regulation of stress responses. The accurate identification of m5U sites is crucial for understanding their biological functions. We propose RNADSN, the first transfer learning deep neural network that learns common features between tRNA m5U and mRNA m5U to enhance the prediction of mRNA m5U. Without seeing the experimentally detected mRNA m5U sites, RNADSN has already outperformed the state-of-the-art method, m5UPred. Using mRNA m5U classification as an additional layer of supervision, our model achieved another distinct improvement and presented an average area under the receiver operating characteristic curve (AUC) of 0.9422 and an average precision (AP) of 0.7855. The robust performance of RNADSN was also verified by cross-technical and cross-cellular validation. The interpretation of RNADSN also revealed the sequence motif of common features. Therefore, RNADSN should be a useful tool for studying m5U modification.
Diastereoselectivity of 5-Methyluridine Osmylation Is Inverted inside an RNA Chain
Bioconjug Chem 2016 Sep 21;27(9):2188-97.PMID:27540864DOI:10.1021/acs.bioconjchem.6b00403.
In this study, we investigated the reaction of the osmium tetroxide-bipyridine complex with pyrimidines in RNA. This reagent, which reacts with the diastereotopic 5-6 double bond, thus leading to the formation of two diastereomers, was used in the past to label thymidine and 5-methylcytosine in DNA. In light of the growing interest in post-transcriptional RNA modifications, we addressed the question of whether this reagent could be used for labeling of the naturally occurring RNA modifications 5-methylcytosine and 5-Methyluridine. On nucleoside level, 5-methylcytosine and 5-Methyluridine revealed a 5- and 12-fold preference, respectively, over their nonmethylated equivalents. Performing the reaction on an RNA level, we could show that the steric environment of a pentanucleotide has a major detrimental impact on the reaction rate of osmylation. Interestingly, this drop in reactivity was due to a dramatic change in diastereoselectivity, which in turn resulted from impediment of the preferred attack via the si side. Thus, while on the nucleoside level, the absolute configuration of the major product of osmylation of 5-Methyluridine was (5R,6S)-5-methyluridine glycol-dioxoosmium-bipyridine, reaction with an RNA pentanucleotide afforded the corresponding (5S,6R)-diastereomer as the major product. The change in diastereoselectivity lead to an almost complete loss of selectivity toward 5-methylcytosine in a pentanucleotide context, while 5-Methyluridine remained about 8 times more reactive than the canonical pyrimidines. On the basis of these findings, we evaluate the usefulness of osmium tetroxide-bipyridine as a potential label for the 5-Methyluridine modification in transcriptome-wide studies.
iRNA-m5U: A sequence based predictor for identifying 5-Methyluridine modification sites in Saccharomyces cerevisiae
Methods 2022 Jul;203:28-31.PMID:33882361DOI:10.1016/j.ymeth.2021.04.013.
The 5-Methyluridine (m5U)modification plays important roles in a series of biological processes. Accurate identification of m5U sites will be helpful to decode its biological functions. Although experimental techniques have been proposed to detect m5U, they are still expensive and time consuming. In the present work, a support vector machine based method, called iRNA-m5U, was developed to identify the m5U sites in the Saccharomyces cerevisiae transcriptome. The performance of iRNA-m5U was validated based on different datasets. The accuracies obtained by iRNA-m5U is promising, indicating that it holds the potential to become an useful tool for the identification of m5U sites.
Influence of fluorine substitution on the molecular conformation of 3'-deoxy-3'-fluoro-5-methyluridine
Acta Crystallogr C Struct Chem 2020 Apr 1;76(Pt 4):346-352.PMID:32229715DOI:10.1107/S2053229620003083.
Fluorine substitutions on the furanose ring of nucleosides are known to strongly influence the conformational properties of oligonucleotides. In order to assess the effect of fluorine on the conformation of 3'-deoxy-3'-fluoro-5-methyluridine (RTF), C10H13FN2O5, we studied its stereochemistry in the crystalline state using X-ray crystallography. The compound crystallizes in the chiral orthorhombic space group P212121 and contains two symmetry-independent molecules (A and B) in the asymmetric unit. The furanose ring in molecules A and B adopts conformations between envelope (2E, 2'-endo, P = 162°) and twisted (2T3, 2'-endo and 3'exo, P = 180°), with pseudorotation phase angles (P) of 164.3 and 170.2°, respectively. The maximum puckering amplitudes, νmax, for molecules A and B are 38.8 and 36.1°, respectively. In contrast, for 5-Methyluridine (RTOH), the value of P is 21.2°, which is between the 3E (3'-endo, P = 18.0°) and 3T4 (3'-endo and 4'-exo, P = 36°) conformations. The value of νmax for RTOH is 41.29°. Molecules A and B of RTF generate respective helical assemblies across the crystallographic 21-screw axis through classical N-H...O aand O-H...O hydrogen bonds supplemented by C-H...O contacts. Adjacent parallel helices of both molecules are linked to each other via O-H...O and O...π interactions.
m5UPred: A Web Server for the Prediction of RNA 5-Methyluridine Sites from Sequences
Mol Ther Nucleic Acids 2020 Sep 30;22:742-747.PMID:33230471DOI:10.1016/j.omtn.2020.09.031.
As one of the widely occurring RNA modifications, 5-Methyluridine (m5U) has recently been shown to play critical roles in various biological functions and disease pathogenesis, such as under stress response and during breast cancer development. Precise identification of m5U sites on RNA is vital for the understanding of the regulatory mechanisms of RNA life. We present here m5UPred, the first web server for in silico identification of m5U sites from the primary sequences of RNA. Built upon the support vector machine (SVM) algorithm and the biochemical encoding scheme, m5UPred achieved reasonable prediction performance with the area under the receiver operating characteristic curve (AUC) greater than 0.954 by 5-fold cross-validation and independent testing datasets. To critically test and validate the performance of our newly proposed predictor, the experimentally validated m5U sites were further separated by high-throughput sequencing techniques (miCLIP-Seq and FICC-Seq) and cell types (HEK293 and HAP1). When tested on cross-technique and cross-cell-type validation using independent datasets, m5UPred achieved an average AUC of 0.922 and 0.926 under mature mRNA mode, respectively, showing reasonable accuracy and reliability. The m5UPred web server is freely accessible now and it should make a useful tool for the researchers who are interested in m5U RNA modification.