2'-Fluorothymidine
(Synonyms: 2'-氟胸苷,2'-?Deoxy-?2'-?fluoro-?5-?Methyluridine) 目录号 : GC35089
2'-Fluorothymidine (2'-Fluoro-2'-deoxythymidine) 是胸腺嘧啶 (TdR) 和甲基尿苷的生物同工酶，是 2 型胸苷激酶 (TK2) 的高度选择性底物。
Cas No.:122799-38-6
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
2'-Fluorothymidine (2'-Fluoro-2'-deoxythymidine), a bioisostere of both thymidine (TdR) and methyluridine, is a putative highly selective substrate for thymidine kinase type 2 (TK2)[1].
[1]. Wiebe LI, et al. Biochemistry and biology of 2'-Fluoro-2'-deoxythymidine (FT), a putative highly selective substrate for thymidine kinase type 2 (TK2). Curr Radiopharm. 2012 Jan;5(1):38-46.
| Cas No. | 122799-38-6 | SDF | |
| 别名 | 2'-氟胸苷,2'-?Deoxy-?2'-?fluoro-?5-?Methyluridine | ||
| Canonical SMILES | OC[C@@H]1[C@H]([C@@H](F)[C@H](N2C(NC(C(C)=C2)=O)=O)O1)O | ||
| 分子式 | C10H13FN2O5 | 分子量 | 260.22 |
| 溶解度 | Soluble in DMSO | 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 | 3.8429 mL | 19.2145 mL | 38.429 mL |
| 5 mM | 0.7686 mL | 3.8429 mL | 7.6858 mL |
| 10 mM | 0.3843 mL | 1.9215 mL | 3.8429 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。
Properties of 2'-fluorothymidine-containing oligonucleotides: interaction with restriction endonuclease EcoRV
Biochemistry 1991 Apr 23;30(16):4001-9.PMID:2018768DOI:10.1021/bi00230a027.
2'-Fluorothymidine (Tf) was synthesized via an improved procedure with (diethylamino)sulfur trifluoride. The compatibility of the analogue with DNA synthesis via the phosphoramidite method was demonstrated after complete enzymatic digestion of the oligonucleotides d(Tf11T) and d(Tf3T), the sole products of which were 2'-Fluorothymidine and thymidine in the expected ratio. The 2'-Fluorothymidine was also incorporated into the EcoRV recognition sequence (underlined), within the complementary oligonucleotides d(CAAACCGATATCGTTGTG) and d(CACAACGATATCGGTTTG). Thermal melting characteristics of these duplexes showed a significant decrease in stability only when both of the thymidine residues in one of the strands were replaced. In contrast, when all of one strand of a duplex contained 2'-Fluorothymidine, as in d(Tf11T).d(A12), a substantially higher Tm and cooperativity of melting was observed relative to the unmodified structure. EcoRV cleaved a duplex that contained a 2'-Fluorothymidine at the scissile linkage in each strand at two-thirds of the rate obtained for the unmodified structure. A duplex containing two 2'-Fluorothymidine residues in one strand and none in the other was cleaved at one-third of the rate in its unsubstituted strand, whereas the cleavage rate was reduced to 22% in its modified strand.
NEIL1 binding to DNA containing 2'-Fluorothymidine glycol stereoisomers and the effect of editing
Chembiochem 2012 Jun 18;13(9):1338-48.PMID:22639086DOI:10.1002/cbic.201200139.
Thymine glycol (Tg), one of the oxidized bases formed in DNA by reactive oxygen species, is repaired by the DNA glycosylases such as NEIL1, NTH1 and Endo III. In our recent studies, we showed that NEIL1's catalytic efficiency and lesion specificity are regulated by an RNA-editing adenosine deamination reaction. In this study, we synthesized oligodeoxynucleotides containing 2'-Fluorothymidine glycol with either ribo or arabino configuration and investigated the binding of these modified DNAs with the unedited and edited forms of human NEIL1 along with E. coli Endo III. For the two forms of hNEIL1, binding affinities to FTg-containing DNA were similar indicating that the editing effect is more subtle than to simply alter substrate affinity. While the NEIL1-binding to FTg-containing DNAs was largely insensitive to C5 and 2' stereochemistry, a preference was observed for the FTg-G pair over the FTg-A pair. In addition, we found that optimal binding is observed with Endo III and duplex DNA with riboFTg(5S) paired with dG. The modified DNAs reported here will provide useful tools for further characterizing the interaction between DNA repair glycosylases and thymine glycol containing DNA.
Synthesis and characterization of oligonucleotides containing 2'-fluorinated thymidine glycol as inhibitors of the endonuclease III reaction
Nucleic Acids Res 2006 Mar 17;34(5):1540-51.PMID:16547199DOI:10.1093/nar/gkl061.
Endonuclease III (Endo III) is a base excision repair enzyme that recognizes oxidized pyrimidine bases including thymine glycol. This enzyme is a glycosylase/lyase and forms a Schiff base-type intermediate with the substrate after the damaged base is removed. To investigate the mechanism of its substrate recognition by X-ray crystallography, we have synthesized oligonucleotides containing 2'-Fluorothymidine glycol, expecting that the electron-withdrawing fluorine atom at the 2' position would stabilize the covalent intermediate, as observed for T4 endonuclease V (Endo V) in our previous study. Oxidation of 5'- and 3'-protected 2'-Fluorothymidine with OsO4 produced two isomers of thymine glycol. Their configurations were determined by NMR spectroscopy after protection of the hydroxyl functions. The ratio of (5R,6S) and (5S,6R) isomers was 3:1, whereas this ratio was 6:1 in the case of the unmodified sugar. Both of the thymidine glycol isomers were converted to the corresponding phosphoramidite building blocks and were incorporated into oligonucleotides. When the duplexes containing 2'-fluorinated 5R- or 5S-thymidine glycol were treated with Escherichia coli endo III, no stabilized covalent intermediate was observed regardless of the stereochemistry at C5. The 5S isomer was found to form an enzyme-DNA complex, but the incision was inhibited probably by the fluorine-induced stabilization of the glycosidic bond.
C2'-F Stereoconfiguration As a Puckering Switch for Base Stacking at the Dinucleotide Level
J Org Chem 2018 Feb 16;83(4):2473-2478.PMID:29364674DOI:10.1021/acs.joc.7b03186.
Fluorine configuration at C2' of the bis(2'-Fluorothymidine) dinucleotide is demonstrated to drive intramolecular base stacking. 2'-β F-Configuration drastically reduces stacking compared to the 2'-α series. Hence, base stacking emerges as being tunable by the C2'-F stereoconfiguration through dramatic puckering variations scrutinized by NMR and natural bond orbital analysis. Accordingly, 2'-β F-isomer photoreactivity is significantly reduced compared to that of the 2'-α F-isomer.
Synthesis of oligonucleotide probes containing 2'-deoxy-2'-fluoronucleosides for cleavage of RNA by RNase H
Biomed Biochim Acta 1990;49(4):161-6.PMID:1698357doi
Modified oligodeoxyribonucleotides containing 3'-terminal 2'-deoxy-2'-fluorouridine (UF) or 2'-Fluorothymidine (TF) were successfully applied for specific RNA hydrolysis by RNase H from E. coli. The nonanucleotides d(CACCGCGCTF) and d(CACCGCGCUF) were synthesized using the phosphoramidite solid support method. The modified nucleosides were immobilized on the CPG support and provided the starting nucleoside residues. Model experiments were carried out using the 5S RNA from E. coli ribosomes and its 1-41 fragment. It was found that the use of this type of modified probes did not decrease neither the efficiency nor the specificity of the RNase H reaction.