9-Ethyladenine
(Synonyms: 9-乙基腺嘌呤) 目录号 : GC38883
9-Ethyladenine 是 APRT (腺嘌呤磷酸核糖基转移酶) 的部分有效抑制剂。
Cas No.:2715-68-6
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
9-Ethyladenine is a partially effective inhibitor of APRT (adenine phosphoribosyltransferase)[1].
[1]. Edamura K, et al. No self-injurious behavior was found in HPRT-deficient mice treated with 9-ethyladenine. Pharmacol Biochem Behav. 1998 Oct;61(2):175-9.
| Cas No. | 2715-68-6 | SDF | |
| 别名 | 9-乙基腺嘌呤 | ||
| Canonical SMILES | NC1=C2C(N(C=N2)CC)=NC=N1 | ||
| 分子式 | C7H9N5 | 分子量 | 163.18 |
| 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 | 6.1282 mL | 30.641 mL | 61.282 mL |
| 5 mM | 1.2256 mL | 6.1282 mL | 12.2564 mL |
| 10 mM | 0.6128 mL | 3.0641 mL | 6.1282 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。
9-Ethyladenine derivatives as adenosine receptor antagonists: 2- and 8-substitution results in distinct selectivities
Naunyn Schmiedebergs Arch Pharmacol 2003 Jun;367(6):629-34.PMID:12734636DOI:10.1007/s00210-003-0749-9.
9-Ethyladenine was used as the basis for a series of non-xanthine adenosine receptor antagonists at human adenosine receptors. The adenine-based compounds were substituted in 2- or 8-position with a variety of side chains including some aryl or arylalkynyl groups previously tested as 2-substituents in adenosine and 5'-N-ethylcarboxamidoadenosine (NECA) for their effect on agonist affinity. The affinity of the novel compounds was tested in radioligand binding assays (A1, A2A and A3) and inhibition of NECA-stimulated adenylyl cyclase activity (A2B) in membranes prepared from CHO cells stably transfected with the respective human receptor subtype. High affinity antagonists were identified for A1 (9-ethyl-8-phenyl-9H-adenine, compound 2; 6-(1-butylamino)-9-ethyl-8-phenyl-9H-purine, compound 3), A2A (8-ethoxy-9-ethyladenine; compound 8) and A3 (9-ethyl-8-phenylethynyl-9H-adenine, compound 5) with selectivities versus other receptor subtypes in the range of 10 to 600. These results demonstrate that adenine is a useful template for further development of high-affinity antagonists with distinct receptor selectivity profiles.
Chlorido-, aqua-, 9-ethylguanine- and 9-ethyladenine-adducts of cytotoxic ruthenium arene complexes containing O,O-chelating ligands
J Inorg Biochem 2007 Nov;101(11-12):1903-12.PMID:17582501DOI:10.1016/j.jinorgbio.2007.04.018.
The synthesis and X-ray structures of a half-sandwich Ru(II)p-cymene beta-diketonato complex as chlorido-, aqua-, 9-ethylguanine- and 9-ethyladenine-adducts are reported. Structural features which contribute to stabilisation of adducts through non-covalent, weak interactions are discussed. The X-ray crystal structure of the cytotoxic complex [(eta(6)-p-cym)Ru(Ph(2)acac)Cl] (1), where Ph(2)acac=1,3-diphenyl-1,3-propanedionate and p-cym=para-cymene, shows that the phenyl rings of the acac-type ligand form a hydrophobic face, conferring lipophilic character on the complex. The structure of the aqua adduct [(eta(6)-p-cym)Ru(Ph(2)acac)H(2)O]CF(3)SO(3).H(2)O.Et(2)O (4.H(2)O.Et(2)O), a possible activated species, possesses a comparatively short Ru-OH(2) bond. In the structure of [(eta(6)-p-cym)Ru(Ph(2)acac)9EtG-N7]CF(3)SO(3).2tol (5.2tol), where tol=toluene and 9EtG=9-ethylguanine, a comparatively long Ru-N7 bond is observed in addition to weak G CH8cdots, three dots, centeredO (Ph(2)acac) H-bonds. The crystal structure of [(eta(6)-p-cym)Ru(acac)9EtA-N7]PF(6) (6), where acac=acetylacetonate and 9EtA=9-Ethyladenine, a rare example of a ruthenium complex containing monodentate adenine, shows a strong H-bonding interaction between N6Hcdots, three dots, centeredO(acac), which may contribute to the selectivity of {(eta(6)-p-cym)Ru(acac)}(+) towards adenine bases.
No self-injurious behavior was found in HPRT-deficient mice treated with 9-Ethyladenine
Pharmacol Biochem Behav 1998 Oct;61(2):175-9.PMID:9738533DOI:10.1016/s0091-3057(98)00095-1.
It has been reported that 9-Ethyladenine (9-EA) is an efficient inhibitor of APRT (adenine phosphoribosyltransferase) and that its administration causes self-injurious behavior (Lesch-Nyhan Syndrome-like symptoms) in HPRT (hypoxanthine-guanine phosphoribosyltransferase)-deficient mice. In contrast, we found neither any self-injurious behavior (SIB), such as visible injury or hair loss, nor any apparent decrease in APRT activity in HPRT-deficient mice treated with 9-EA. We also found that 9-EA has little irreversible or competitive inhibitory effect on APRT in vitro, even at a concentration of 10(-2) M. In light of the negative finding of SIB in APRT/HPRT double-deficient mice, it seems unlikely that SIB in HPRT-deficient mice is caused by lowered APRT activity. It is concluded that 9-EA is not a sufficient APRT inhibitor and cannot be used in experiments that mimic lowered APRT status in an animal model.
Hydrogen bonding interaction of diphenylhydantoin and 9-Ethyladenine
Mol Pharmacol 1983 Mar;23(2):273-7.PMID:6835197doi
A hydrogen-bonded complex of diphenylhydantoin (DPH) and 9-Ethyladenine (EtAd) crystallizes from 2,4-pentanedione with the asymmetrical unit consisting of two DPH molecules, one EtAd molecule, and one solvent molecule. The crystal structure was solved by direct methods and refined to a residual of R = 0.054. Structure determination reveals that one DPH hydrogen-bonds to EtAd in a Watson-Crick scheme while the second DPH N(3)--H bonds to EtAd N(3) to form a 2:1 DPH-EtAd complex. Comparisons are made with barbiturate-adenine complexes and with an earlier postulation of a 1:1 DPH-EtAd complex derived from NMR and IR data. The 2,4-pentanedione molecule adopts the keto-enol configuration with an asymmetrical intramolecular hydrogen bond.
The Length and Flexibility of the 2-Substituent of 9-Ethyladenine Derivatives Modulate Affinity and Selectivity for the Human A2A Adenosine Receptor
ChemMedChem 2016 Aug 19;11(16):1829-39.PMID:27037522DOI:10.1002/cmdc.201500595.
The A2A adenosine receptor (A2A AR) is a key target for the development of pharmacological tools for the treatment of central nervous system disorders. Previous works have demonstrated that the insertion of substituents at various positions on adenine leads to A2A AR antagonists with affinity in the micromolar to nanomolar range. In this work, a series of 9-Ethyladenine derivatives bearing phenylalkylamino, phenylakyloxy or phenylakylthio groups of different lengths at the 2-position were synthesised and tested against the human adenosine receptors. The derivatives showed sub-micromolar affinity for these membrane proteins. The further introduction of a bromine atom at the 8-position has the effect of improving the affinity and selectivity for all ARs and led to compounds that are able bind to the A2A AR subtype at low nanomolar levels. Functional studies confirmed that the new adenine derivatives behave as A2A AR antagonists with half-maximal inhibitory concentration values in the nanomolar range. Molecular modelling studies provide a description of the possible binding mode of these compounds at the A2A AR and an interpretation of the affinity data at this AR subtype.