beta-L-D4A
(Synonyms: 2',3'-二脱氧-2',3'-二氢腺苷,2'3'-didehydro-2'3'-dideoxyadenosine) 目录号 : GC33989
beta-L-D4A 是一种核苷 HIV-1 逆转录酶抑制剂。
Cas No.:7057-48-9
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
beta-L-D4A is a nucleoside HIV-1 reverse transcriptase inhibitor.
beta-L-D4A is a nucleoside HIV-1 reverse transcriptase inhibitor. Results confirm that the biological activity of NSC 108602 is connected with the termination of the DNA chain synthesis in the 5′-3′ direction[1]
Reference:
[1]. Ponomareva AG, et al. Structural and energetic properties of the potential HIV-1 reverse transcriptase inhibitors d4A and d4G: a comprehensive theoretical investigation. J Biomol Struct Dyn. 2014;32(5):730-40.
| Cas No. | 7057-48-9 | SDF | |
| 别名 | 2',3'-二脱氧-2',3'-二氢腺苷,2'3'-didehydro-2'3'-dideoxyadenosine | ||
| Canonical SMILES | OC[C@@H](O1)C=C[C@@H]1N2C=NC3=C(N)N=CN=C32 | ||
| 分子式 | C10H11N5O2 | 分子量 | 233.23 |
| 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 | 4.2876 mL | 21.4381 mL | 42.8761 mL |
| 5 mM | 0.8575 mL | 4.2876 mL | 8.5752 mL |
| 10 mM | 0.4288 mL | 2.1438 mL | 4.2876 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。
Effect and mechanism of beta-L-D4A on DNA polymerase alpha
World J Gastroenterol 2007 Dec 14;13(46):6243-8.PMID:18069767DOI:10.3748/wjg.v13.i46.6243.
Aim: To investigate the safety of beta-L-D4A on DNA polymerase alpha. Methods: Ion exchange chromatography was used to separate DNA polymerase alpha from crude extract of human Hela cells. Detailed kinetic parameters were determined for beta-L-D4A against DNA polymerase alpha. Results: DNA polymerase alpha was purified with 4% yield and 31000 units/mg specific activity. The Michaelis constant (Km = 3.22 micromol/L), 50% inhibition concentration (IC50 = 178.49 micromol/L) and inhibition constant (Ki = 126 micromol/L) of beta-L-D4A were determined by kinetic analysis. Conclusion: beta-L-D4A is a more safe nucleoside for hepatitis B virus infection with a lower host toxicity.
Efficacies of beta-L-D4A against Hepatitis B virus in 2.2.15 cells
World J Gastroenterol 2008 Feb 28;14(8):1263-7.PMID:18300355DOI:10.3748/wjg.14.1263.
Aim: To investigate the antiviral effect of beta-L-enantiomer of 2',3'-didehydro-2',3'-dideoxyadenosine (beta-L-D4A) on 2.2.15 cells transfected with the hepatitis B virus (HBV) genome. Methods: Lamivudine (3TC) as a positive control. Then, HBV DNA in treated 2.2.15 cells and the Hepatitis B surface antigen (HBsAg) in the culture supernatants were detected to determine the inhibitory effect of beta-L-D4A. At the same time, 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) was used to detect the survival ratio of 2.2.15 cells. Results: beta-L-D4A has a dose-dependent inhibitory effect on HBV DNA replication; this effect was apparent when the concentration was above 1 mol/L. When beta-L-D4A was at the highest concentration, 100 mol/L, the HBsAg inhibition ratio was above 50%. The Therapeutic index (TI) of beta-L-D4A was above 2.1. Conclusion: beta-L-D4A has a dose-dependent inhibitory effect on the replication of HBV DNA and the secretion of HBsAg at low toxicity.
Inhibition of hepatitis B virus by a novel L-nucleoside, beta-L-D4A and related analogues
World J Gastroenterol 2003 Aug;9(8):1840-3.PMID:12918134DOI:10.3748/wjg.v9.i8.1840.
Aim: To explore the inhibition of beta-L-D4A on hepatitis B virus (HBV) in 2.2.15 cells derived from HepG2 cells transfected with HBV genome. Methods: 2.2.15 cells were plated at a density of 5X104 per well in 12-well tissue culture plates, and treated with various concentrations of beta-L-D4A for 6 days. In the end, 5 microl of medium was used for the estimation of HBsAg and HBeAg, the other medium was processed to obtain virions by a polyethylene glycol precipitation method. At the same time, intracellular DNA was also extracted and digested with HindIII. Both DNAs were subjected to Southern blot, hybridized with a (32)P-labeled HBV probe and autoradiographed. Intensity of the autoradiographic bands was quantitated by densitometric scans of computer and ED(50) was calculated. Then Hybond-N membrane was washed and rehybridized with a (32)P-labeled mtDNA-specific probe, and effect of beta-L-D4A on mitochondrial DNA was studied. 2.2.15 cells were also seeded in 24-well tissue culture plates, and cytotoxicity with different concentrations was examined by MTT method. ID(50) was calculated. Structure-activity relationships between D2A and D4A were also studied as above. Results: Autoradiographic bands were similar between supernatant and intracellular HBV DNA. Episomal HBV DNA was inhibited in a dose-dependent manner. ED(50) was 0.2 microM. HBsAg or HBeAg was not apparently decreased, and inhibition of mitochondrial DNA was not obvious. The experiment of cytotoxicity gained ID(50) at 200 microM. Conclusion: beta-L-D4A possesses potent inhibitory effects on the replication of HBV in vitro with little cytotoxicity and mitochondrial toxicity, TI value is 1000. It is expected to be developed as a new clinically anti-HBV drug.
[Synthesis of a novel L-nucleoside, beta-L-D4A and its inhibition on the replication of hepatitis B virus in vitro]
Yao Xue Xue Bao 2005 Sep;40(9):825-9.PMID:16342685doi
Aim: Nucleoside analogues have become the most promising candidates of anti-HBV drugs. In this study, beta-L-D4A was synthesized and explored its inhibitiory action against hepatitis B virus (HBV) in 2. 2. 15 cells derived from HepG2 cells transfected with HBV genome. Methods: beta-L-D4A was stereo-controlled synthesized from D-glutamic acid, and the structure was identified by IR, 1H NMR and MS. 2. 2. 15 Cells were placed at a density of 5 x 10(4) per well in 12-well tissue culture plates, and treated with various concentrations of beta-L-D4A for 6 days. At the end, medium was processed to obtain virions by a polyethlene glycol precipitation method. At the same time, intracellular DNA was also extracted and digested with Hind III. Both of the above DNA were subjected to Southern blot, hybridized with a 32P-labeled HBV probe and autoradiographed. The intensity of the autoradiographic bands was quantitated by densitometric scans of computer and EC50 was calculated. 2. 2. 15 cells were also seeded in 24-well tissue culture plates, and cytotoxicity with different concentrations was examined by MTT method. IC50 was calculated. Results: The synthesized compound structure conformed with beta-L-D4A; Autoradiographic bands showed similar for supernatant and intracellular HBV DNA. Episomal HBV DNA was inhibited in a dose-dependent manner. EC50 0.2 micromol x L(-1). The experiment of cytotoxicity gained IC50 200 micromol x L(-10. Conclusion: beta-L-D4A has been synthesized successfully. beta-L-D4A possessed potent inhibitory effect on replication of HBV in vitro with low cytotoxicity, TI value was 1 000. It is expected to be developed clinically into a new anti-HBV drug.
[Effect and mechanism of beta-L-D4A (a novel nucleoside analog) against hepatitis B virus]
Zhonghua Gan Zang Bing Za Zhi 2003 May;11(5):268-70.PMID:12773236doi
Objective: To explore the effect and the molecular targets of anti-hepatitis B virus (HBV) by beta-L-D4A in vitro. Methods: 2.2.15 cells were cultured and treated with various concentrations of beta-L-D4A for 6 hours, then the effect of anti-HBV was examined by Southern blot and the replicating core particles from the cells were isolated. The endogenous polymerase reaction and activity gel experiment were performed to monitor the activities of the DNA polymerase and reverse transcriptase. Results: The replication of HBV DNA was inhibited in a dose-dependent manner. The endogenous polymerase reaction showed both the two enzymatic activities were irreversibly inactivated in a concentration -dependent manner, with IC50 at 0.51 micromol/L and 0.55 micromol/L, respectively. But the activities of DNA polymerase and reverse transcriptase were found to remain active by activity gel with exogenous templates. Conclusions: The mechanism of inhibiting HBV replication by beta-L-D4A may be in that either the DNA replication priming is blocked or the elongation of DNA chain is terminated irreversibly.