2-Fluoroadenine
(Synonyms: 2-氟-6-氨基嘌呤) 目录号 : GC46545
A heterocyclic building block
Cas No.:700-49-2
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-Fluoroadenine is a heterocyclic building block that has been used in the synthesis of heat shock protein 90 (Hsp90) inhibitors that have anticancer activity in vitro.1 It is also cytotoxic to CEM human leukemia cells with an IC50 value of 0.15 µM.2
1.Llauger, L., He, H., Kim, J., et al.Evaluation of 8-arylsulfanyl, 8-arylsulfoxyl, and 8-arylsulfonyl adenine derivatives as inhibitors of the heat shock protein 90J. Med. Chem.48(8)2892-2905(2005) 2.Parker, W.B., Allan, P.W., Shaddix, S.C., et al.Metabolism and metabolic actions of 6-methylpurine and 2-fluoroadenine in human cellsBiochem. Pharmacol.55(10)1673-1681(1998)
| Cas No. | 700-49-2 | SDF | |
| 别名 | 2-氟-6-氨基嘌呤 | ||
| Canonical SMILES | NC1=C2C(N=CN2)=NC(F)=N1 | ||
| 分子式 | C5H4FN5 | 分子量 | 153.1 |
| 溶解度 | DMSO: slightly soluble,Ethanol: slightly soluble | 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 | 6.5317 mL | 32.6584 mL | 65.3168 mL |
| 5 mM | 1.3063 mL | 6.5317 mL | 13.0634 mL |
| 10 mM | 0.6532 mL | 3.2658 mL | 6.5317 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。
Intratumoral generation of 2-Fluoroadenine to treat solid malignancies of the head and neck
Head Neck 2019 Jun;41(6):1979-1983.PMID:30633420DOI:10.1002/hed.25627.
This report describes treatment of locoregional head and neck squamous cell carcinoma (HNSCC) by an innovative, experimental strategy involving generation of a robust anti-cancer agent (2-Fluoroadenine [F-Ade]) following transduction by Escherichia coli purine nucleoside phosphorylase (PNP) in a small number of tumor cells. F-Ade works by a unique mechanism of action (ablation of RNA and protein synthesis) and confers tumor regressions of otherwise refractory HNSCC in human subjects. Clinical studies have now advanced to a pivotal (registration-directed) trial involving locoregional HNSCC, with plans to begin subject enrollment late in 2018. The present review is the first to summarize use of PNP in the context of HNSCC, and provides background regarding this emerging anti-cancer approach.
Convenient synthesis of 2'-deoxy-2-fluoroadenosine from 2-Fluoroadenine
Nucleosides Nucleotides Nucleic Acids 2003 Oct;22(10):1899-905.PMID:14609229DOI:10.1081/NCN-120025237.
A convenient synthesis of 2'-deoxy-2-fluoroadenosine from commercially available 2-Fluoroadenine is described. The coupling reaction of silylated 2-Fluoroadenine with phenyl 3,5-bis[O-(t-butyldimethylsilyl)]-2-deoxy-1-thio-D-erythro-pentofuranoside gave the corresponding 2-fluoro-2'-deoxyadenosine derivative (alpha/beta = 1:1) in good yield. The alpha- and beta-anomers were separated by chromatography, and then desilylated to give compounds 1a and 1b.
2-fluoro-ATP: a toxic metabolite of 9-beta-D-arabinosyl-2-fluoroadenine
Biochem Biophys Res Commun 1983 May 31;113(1):35-43.PMID:6860342DOI:10.1016/0006-291x(83)90428-x.
Murine P388 cells incubated in vitro with the anticancer drug arabinosyl 2-Fluoroadenine accumulate its 5'-triphosphate, F-araATP, as the major phosphorylated metabolite. A new chromatographically separate metabolite that accumulated to levels 10% of that of F-araATP was identified as 2-fluoro-ATP, by the following criteria. 1. The metabolite coeluted with the authentic compound on anion-exchange HPLC. 2. Dephosphorylation of the metabolite yielded a compound that was chromatographically identical to 2-fluoroadenosine. 3. The compound was sensitive to NaIO4 oxidation. Cellular incubation experiments indicated that 2-Fluoroadenine, but not arabinosyl 2-fluorohypoxanthine, was the likely intermediate in the formation of 2-fluoro-ATP.
Phosphorolytic cleavage of 2-Fluoroadenine from 9-beta-D-arabinofuranosyl-2-fluoroadenine by Escherichia coli. A pathway for 2-fluoro-ATP production
Biochem Pharmacol 1987 Sep 15;36(18):2945-50.PMID:3307790DOI:10.1016/0006-2952(87)90207-3.
2-Fluoroadenine (F-Ade) is a metabolite of 9-beta-D-arabinofuranosyl-2-fluoroadenine (F-ara-A) that may be involved in the development of toxic side effects from this anticancer drug. The liberation of F-Ade from F-ara-A has been examined in different biological systems. Extracts of Escherichia coli but not mammalian cells or tissues catalyzed the conversion of F-ara-A to F-Ade with apparent Km and Vmax values of 1350 microM and 7.7 nmol/min/mg protein respectively. This reaction depended on the presence of phosphate and was inhibited by purine nucleosides in a competitive manner, indicating that the enzyme responsible for the conversion is purine nucleoside phosphorylase. After incubation of intact bacteria with 100 microM [3H]F-ara-A, [3H]F-Ade was the same percentage of cellular radioactivity as in the medium, but it was only one-tenth the concentration of F-ara-A in the cells. In contrast, the cellular concentration of 2-fluoro-ATP was 20-fold greater than that of F-ara-A-5'-triphosphate. These results suggest that F-ara-A entered the bacteria intact and was phosphorolytically cleaved to liberate F-Ade, which would have been either anabolized to the toxic triphosphate or excreted. The latter pathway would provide a route by which F-Ade might be absorbed into the host circulation.
Characterization of 2-Fluoro-2'-deoxyadenosine in Duplex, G-Quadruplex and i-Motif
Chembiochem 2022 Jun 20;23(12):e202200222.PMID:35438834DOI:10.1002/cbic.202200222.
Among various kinds of fluorine-substituted biomolecules, 2-Fluoroadenine (2FA) and its derivatives have been actively investigated as therapeutic reagents, radio-sensitizers, and 19 F NMR probes. In spite of their excellent properties, DNA containing 2FA has not been studied well. For fundamental understanding and future applications to the development of functional nucleic acids, we characterized 2FA-containing oligonucleotides for canonical right-handed DNA duplex, G-quadruplex, and i-motif structures. Properties of 2FA were similar to native adenine due to the small size of the fluorine atom, but it showed unique features caused by high electronegativity. This work provides useful information for future application of 2FA-modified DNA.