3'-Amino-3'-deoxyadenosine
目录号 : GC67662
3'-Amino-3'-deoxyadenosine 是一种从蠕孢菌中提取的抗肿瘤剂。
Cas No.:2504-55-4
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
3'-Amino-3'-deoxyadenosine is an antitumor agent extracted from Helminthosporium[1].
[1]. Gerber, Nancy Nichols, et al. 3'-Amino-3'-deoxyadenosine, an antitumor agent from Helminthosporium.
| Cas No. | 2504-55-4 | SDF | Download SDF |
| 分子式 | C10H14N6O3 | 分子量 | 266.26 |
| 溶解度 | 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 | 3.7557 mL | 18.7786 mL | 37.5573 mL |
| 5 mM | 0.7511 mL | 3.7557 mL | 7.5115 mL |
| 10 mM | 0.3756 mL | 1.8779 mL | 3.7557 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。
Analogs of 3'-Amino-3'-deoxyadenosine inhibit HIV-1 replication
AIDS Res Hum Retroviruses 1989 Dec;5(6):647-53.PMID:2611044DOI:10.1089/aid.1989.5.647.
Several different nucleoside analogs have been demonstrated to inhibit retroviral RNA-dependent DNA polymerase activity in preference to cellular DNA-dependent DNA polymerases. 3'-Amino derivatives of 3-deoxyadenosine was analyzed for their antiviral activity toward HIV-1 and for their host cell toxicity. Puromycin aminonucleoside (PANS), PANS 5'-monophosphate, and 3'-Amino-3'-deoxyadenosine triphosphate all inhibited HIV-1 replication in acutely infected cells. No significant antiviral effects of PANS were demonstrated in chronically infected cells. The effect of PANS was demonstrated at an early step in HIV-1 replication, most likely reverse transcription. 3'-Aminonucleoside analogs are a novel class of inhibitors of HIV-1 replication that require further analysis in cell culture and animal studies.
A practical route to 3'-Amino-3'-deoxyadenosine derivatives and puromycin analogues
J Org Chem 2003 Mar 7;68(5):2038-41.PMID:12608833DOI:10.1021/jo026627c.
3'-aminoacylamino-3'-deoxyadenosines, analogues of the antibiotic puromycin, have been synthesized from adenosine. They key 3'-azido derivative 10 was obtained through a 3'-oxidation/reduction/substitution procedure. A modified purification protocol on a larger scale was developed for the oxidation step using the Garegg reagent. The coupling reaction between an Fmoc-l-amino acid and the fully protected form of 3'-Amino-3'-deoxyadenosine 11 furnished the aminoacylated compounds 12 in high yields. The puromycin analogues were obtained in 10 steps and up to 23% (14c) overall yield.
Solution conformational analysis of 2'-amino-2''deoxyadenosine, 3'-Amino-3'-deoxyadenosine and puromycin by pulsed nuclear-magnetic-resonance methods
Eur J Biochem 1977 Oct 17;80(1):295-304.PMID:303566DOI:10.1111/j.1432-1033.1977.tb11882.x.
The solution conformation of 2'-amino-2'-deoxyadenosine, 3'-Amino-3'-deoxyadenosine, and 3'-amino-3'-deoxy-6-N,N-dimethyladenosine have been determined by nuclear magnetic resonance in aqueous and ammonia solutions. The analysis of the ribose moiety is based on the two-state S in equilibrium N model of Altona and Sundaralingam. Longitudinal proton relaxation time and nuclear Overhauser enchancement measurements have been carried out in order to characterize the orientation of the base relative to the ribose. Those studies indicate that 3'-Amino-3'-deoxyadenosine and 3'-amino-3'-deoxy-6-N,N-dimethyladenosine exist in solution preferentially in the N-anti-g + conformations. On the other hand, 2'-amino-2'-deoxyadenosine adopts the S-syn-g +/t conformation families. It appears that the base is restricted to the anti conformation in the first two compounds, while in 2'-amino-2'-deoxyadenosine, one third of the molecules in the S state are in the anti range. These studies corroborate the previously proposed correlations between the N state of the ribose and the anti orientation of the base and between the S state of the ribose and the syn orientation of the base.
2',3'-Bis(2-chloroethyl)aminophosphoryl-3'-amino-3'-deoxyadenosine: a cyclic nucleotide with antitumor activity
J Med Chem 1979 Jul;22(7):882-5.PMID:448687DOI:10.1021/jm00193a026.
The synthesis of the title compound from 3'-Amino-3'-deoxyadenosine in 40% yield is reported. 3'-Amino-3'-deoxyadenosine was made by an improved synthesis in 12 steps from inexpensive D-xylose in 15% overall yield. Both isomers of the title compound, separated by column chromatography, possess confirmed activity against KB tumor cell cultures.
Derivatives of 3'- and 5'-deoxyadenosine: their inhibitory activity against DNA viruses
Chemotherapy 1980;26(5):316-22.PMID:6967001DOI:10.1159/000237923.
3'-Deoxyadenosine, 3'-Amino-3'-deoxyadenosine (3'3'), nine derivatives therefrom, two derivatives of 5'-amino-5'-deoxyadenosine and three derivates of 3', 5'-dideoxyadenosine were tested in cell culture for antiviral activity against three DNA viruses: adenovirus 5, herpesvirus hominis 1, and vaccinia virus. Cytotoxicity was also assessed. (3'3') derivatives affected the multiplication of all three viruses similarly. Those which were effective were also cytotoxic at the same or slightly higher concentration. Substitution or other molecular modification of (3'3') tend to lower the biological activity. The presence of an adenosine deaminase inhibitor enhanced both antiviral activity against adenovirus 5 and cytotoxicity in (3'3') compounds, but not in the others. Both 5'-amino-5'-deoxyadenosine compounds were active against vaccinia virus only. Of the three 3', 5'-dideoxyadenosines, only one had both cytotoxic and antiviral activity. Most, if not all, seemingly antiviral effects appear to be caused by inhibition of the cell metabolism.