3-Deazaadenosine
(Synonyms: 3-脱氮腺苷) 目录号 : GC14713
3-Deazaadenosine（盐酸盐）是 S-腺苷高半胱氨酸水解酶的抑制剂，Ki 为 3.9 µM。
Cas No.:6736-58-9
Sample solution is provided at 25 µL, 10mM.
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3-Deazaadenosine (hydrochloride) is an inhibitor of S-adenosylhomocysteine hydrolase, with a Ki of 3.9 µM[1].
3-Deazaadenosine dose-dependently prevented the proliferation and migration of human coronary VSMCs in vitro. This was accompanied by an increased expression of the cyclin-dependent kinase inhibitors p21(WAF1/Cip1), p27(Kip1), a decreased expression of G(1)/S phase cyclins, and a lack of retinoblastoma protein hyperphosphorylation. [3]. In the mouse macrophage cell line, RAW264. S-Adenosylhomocysteine accumulated in cells incubated with 3-deazaaristeromycin while S-3-deazaadenosylhomocysteine was the major product in cells incubated with 3-Deazaadenosine and homocysteine thiolactone[4].200 microM 3-Deazaadenosine (c3Ado) prevented this TNF-induced increase in HEC adhesiveness. This effect resulted from interactions of 3-Deazaadenosine with HEC and not with polymorphonuclear neutrophils[5]. 3-Deazaadenosine (DZA), an adenosine analogue, prevented high methionine-induced ICAM-1 and VCAM-1 expression and collagen type-1 synthesis.in vitro 3-Deazaadenosine and CBS gene therapy successfully treated the HHcy-induced inflammatory reaction in the methionine metabolism pathway[6].
3-Deazaadenosine (c3Ado) inhibits atherogenesis in mice. Sprague Dawley rats underwent balloon angioplasty. 3-Deazaadenosine was administered orally, starting 5 days prior to the balloon injury and continued for 2 weeks. Fourteen days after balloon injury the intima/media ratio in the c3Ado-treated group was reduced by 67% and luminal stenosis by 50%. Neointimal cellular density was decreased by 25% and the induction of c-Jun and ki67 was markedly lower. Short-term administration of C3Ado inhibits neointima-formation in rats for at least 3 months after injury[7].
References:
[1]: Gordon RK, Ginalski K, et,al. Anti-HIV-1 activity of 3-deaza-adenosine analogs. Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners. Eur J Biochem. 2003 Sep;270(17):3507-17. doi: 10.1046/j.1432-1033.2003.03726.x. PMID: 12919315.
[2]: Jeong SY, Ahn SG, et,al. 3-deazaadenosine, a S-adenosylhomocysteine hydrolase inhibitor, has dual effects on NF-kappaB regulation. Inhibition of NF-kappaB transcriptional activity and promotion of IkappaBalpha degradation. J Biol Chem. 1999 Jul 2;274(27):18981-8. doi: 10.1074/jbc.274.27.18981. PMID: 10383397.
[3]: Sedding DG, TrÖbs M, et,al. 3-Deazaadenosine prevents smooth muscle cell proliferation and neointima formation by interfering with Ras signaling. Circ Res. 2009 May 22;104(10):1192-200. doi: 10.1161/CIRCRESAHA.109.194357. Epub 2009 Apr 16. PMID: 19372464.
[4]: Backlund PS Jr, Carotti D, et,al. Effects of the S-adenosylhomocysteine hydrolase inhibitors 3-deazaadenosine and 3-deazaaristeromycin on RNA methylation and synthesis. Eur J Biochem. 1986 Oct 15;160(2):245-51. doi: 10.1111/j.1432-1033.1986.tb09963.x. PMID: 3769925.
[5]: Jurgensen CH, Huber BE, et,al. 3-deazaadenosine inhibits leukocyte adhesion and ICAM-1 biosynthesis in tumor necrosis factor-stimulated human endothelial cells. J Immunol. 1990 Jan 15;144(2):653-61. PMID: 1967270.
[6]: Sen U, Tyagi N, et,al. Cystathionine-beta-synthase gene transfer and 3-deazaadenosine ameliorate inflammatory response in endothelial cells. Am J Physiol Cell Physiol. 2007 Dec;293(6):C1779-87. doi: 10.1152/ajpcell.00207.2007. Epub 2007 Sep 13. PMID: 17855772.
[7]: Seeger FH, Hess W, et,al. The nucleotide analogue 3-deazaadenosine prevents neointima-formation after balloon injury. Biochem Biophys Res Commun. 2009 Jan 23;378(4):826-31. doi: 10.1016/j.bbrc.2008.11.151. Epub 2008 Dec 12. PMID: 19070587.
3-Deazaadenosine（盐酸盐）是 S-腺苷高半胱氨酸水解酶的抑制剂，Ki 为 3.9 µM[1]。
3-Deazaadenosine 具有剂量依赖性在体外阻止人冠状动脉血管平滑肌细胞的增殖和迁移。这伴随着细胞周期蛋白依赖性激酶抑制剂 p21(WAF1/Cip1)、p27(Kip1) 的表达增加、G(1)/S 期细胞周期蛋白的表达减少以及视网膜母细胞瘤蛋白过度磷酸化的缺乏。 [3].在小鼠巨噬细胞系中，RAW264。 S-Adenosylhomocysteine 在与 3-deazaaristeromycin 孵育的细胞中积累，而 S-3-deazaadenosylhomocysteine 是在与 3-Deazaadenosine 和 homocysteine thiolactone [4] 孵育的细胞中的主要产物。200 μM 3-Deazaadenosine (c3Ado) 阻止了这种 TNF 诱导的增加HEC 粘合性。这种作用是由于 3-脱氮腺苷与 HEC 的相互作用而不是与多形核中性粒细胞的相互作用 [5]。 3-脱氮腺苷 (DZA) 是一种腺苷类似物，可阻止高甲硫氨酸诱导的 ICAM-1 和 VCAM-1 表达以及 1 型胶原合成。体外 3-脱氮腺苷和 CBS 基因疗法成功治疗了 HHcy 诱导的炎症反应蛋氨酸代谢途径[6]。
3-脱氮腺苷（c3Ado）抑制小鼠动脉粥样硬化形成。 Sprague Dawley 大鼠接受了球囊血管成形术。 3-脱氮腺苷口服给药，从球囊损伤前 5 天开始，持续 2 周。球囊损伤后 14 天，c3Ado 治疗组的内膜/中膜比率降低了 67%，管腔狭窄降低了 50%。新内膜细胞密度降低了 25%，c-Jun 和 ki67 的诱导显着降低。短期给予 C3Ado 可抑制大鼠损伤后至少 3 个月的新内膜形成[7]。
| Kinase experiment [1]: | |
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Preparation Method |
Prior to use, the [8-14C] adenosine was checked for purity using isocratic HPLC elution. The assay incubation mixture contained 0.4 IU of enzyme in 50 L. The metabolites were separated by thin-layer chromatography. The radioactivity was quantitated by cutting the plastic backed TLC plates and placing them in scintillation vials, and counting in a Packard 2000 CA scintillation counter |
|
Applications |
IC50: 0.15 (HIV-1, A012 isolate), 0.20 µM (HIV-1, A018 isolate). 3-Deazaadenosine (hydrochloride) is an inhibitor of S-adenosylhomocysteine hydrolase, with a Ki of 3.9 µM. |
| Cell experiment [2]: | |
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Cell lines |
Mouse macrophage RAW 264.7 |
|
Preparation Method |
RAW 264.7 cells were pretreated with or without 3-Deazaadenosine (100 μMM) for 1 h, and stimulated by the addition of LPS (1 μg/ml). After incubation for 1 h, the cells were washed, and p65 was recovered by immunoprecipitation with anti-p65 and protein A-Sepharose. |
|
Reaction Conditions |
0-100 μM 3-Deazaadenosine for 1 hour |
|
Applications |
3-Deazaadenosine (1-100 ?M) inhibits LPS-induced expression of TNF-α mRNA, increases DNA binding activity of NF-κB, and causes proteolytic degradation of IκBα, but Not IκBβ in RAW 264.7 cells. 3-Deazaadenosine (100 µM) enhances nuclear translocation of NF-κB, but blocks LPS-induced NF-κB transcriptional activity, and such inhibition is augmented by the addition of homocysteine. |
| Animal experiment [3]: | |
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Animal models |
Male, healthy Sprague–Dawley rats (300‿50 g) |
|
Preparation Method |
Animals and balloon injury: rats were fed for 5 days prior and 14 days after the balloon injury with standard chow containing c3Ado at a concentration of 10 mg/kg 3-Deazaadenosine body weight. |
|
Dosage form |
10 mg/kg 3-Deazaadenosine for 5 days prior and 14 days after the balloon injury |
|
Applications |
3-deazaadenosine (c3Ado) inhibits atherogenesis in mice. Sprague Dawley rats underwent balloon angioplasty. C3Ado was administered orally, starting 5 days prior to the balloon injury and continued for 2 weeks. Fourteen days after balloon injury the intima/media ratio in the c3Ado-treated group was reduced by 67% and luminal stenosis by 50%. Neointimal cellular density was decreased by 25% and the induction of c-Jun and ki67 was markedly lower. |
|
References: [1]. Gordon RK, Ginalski K, et,al. Anti-HIV-1 activity of 3-deaza-adenosine analogs. Inhibition of S-adenosylhomocysteine hydrolase and nucleotide congeners. Eur J Biochem. 2003 Sep;270(17):3507-17. doi: 10.1046/j.1432-1033.2003.03726.x. PMID: 12919315. [2]. Sedding DG, Tr?bs M, et,al.3-Deazaadenosine prevents smooth muscle cell proliferation and neointima formation by interfering with Ras signaling. Circ Res. 2009 May 22;104(10):1192-200. doi: 10.1161/CIRCRESAHA.109.194357. Epub 2009 Apr 16. PMID: 19372464. [3]. Seeger FH, Hess W, et,al.The nucleotide analogue 3-deazaadenosine prevents neointima-formation after balloon injury. Biochem Biophys Res Commun. 2009 Jan 23;378(4):826-31. doi: 10.1016/j.bbrc.2008.11.151. Epub 2008 Dec 12. PMID: 19070587. |
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| Cas No. | 6736-58-9 | SDF | |
| 别名 | 3-脱氮腺苷 | ||
| 化学名 | (2R,3R,4S,5R)-2-(4-amino-1H-imidazo[4,5-c]pyridin-1-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol | ||
| Canonical SMILES | NC1=C2C(N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)=CC=N1 | ||
| 分子式 | C11H14N4O4 | 分子量 | 266.25 |
| 溶解度 | ≥ 26.6mg/mL 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 | 3.7559 mL | 18.7793 mL | 37.5587 mL |
| 5 mM | 0.7512 mL | 3.7559 mL | 7.5117 mL |
| 10 mM | 0.3756 mL | 1.8779 mL | 3.7559 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。
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Quality Control & SDS
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- Purity: >98.00%
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