Nebularine
(Synonyms: 9-(Β-D-呋喃核糖)嘌呤) 目录号 : GC47760
A purine ribonucleoside with diverse biological activities
Cas No.:550-33-4
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
Nebularine is a purine ribonucleoside and an adenosine analog that has been found in L. nebularis and has diverse biological activities.1,2,3,4,5 It reduces herpes simplex virus 1 (HSV-1) viral plaque formation in Vero cells (IC50 = 0.6 µM) and is active against M. phlei, M. avium, M. tuberculosis, and B. abortus.1,2 Nebularine (10 and 100 µM) is cytotoxic to COS-7 cells and induces pyknosis in mouse sarcoma 180 cells and mouse embryonic skin explants in a concentration-dependent manner.3,4 It inhibits root growth of wheat seedlings when used at concentrations ranging from 0.1 to 2 mM.2 Nebularine also inhibits adenosine deaminase (Ki = 16 µM).5
1.JuliÁn-Ortiz, J.V., GÁlvez, J., MuÑoz-Collado, C., et al.Virtual combinatorial syntheses and computational screening of new potential anti-herpes compoundsJ. Med. Chem.42(17)3308-3314(1999) 2.Brown, E.G., and Konuk, M.Plant cytotoxicity of nebularine (purine riboside)Phytochemistry37(6)1589-1592(1994) 3.Tkacz, K., Cioroch, M., Skladanowski, A.C., et al.The cytotoxic effect of purine riboside on COS-7 cellsPurine and Pyrimidine Metabolism in Man X. Advances in Experimental Medicine and Biology486355-359(2000) 4.Biesele, J.J., Slautterback, C., and Margolis, M.Unsubstituted purine and its riboside as toxic antimetabolites in mouse tissue culturesCancer8(1)87-96(1955) 5.Shewach, D.S., Krawczyk, S.H., Acevedo, O.L., et al.Inhibition of adenosine deaminase by azapurine ribonucleosidesBiochem. Pharmacol.44(9)1697-1700(1992)
| Cas No. | 550-33-4 | SDF | |
| 别名 | 9-(Β-D-呋喃核糖)嘌呤 | ||
| Canonical SMILES | O[C@@H]1[C@H](O)[C@@H](CO)O[C@@]1([H])N2C=NC3=CN=CN=C32 | ||
| 分子式 | C10H12N4O4 | 分子量 | 252.2 |
| 溶解度 | DMF: 15 mg/ml,DMSO: 30 mg/ml,PBS (pH 7.2): 1 mg/ml | 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 | 3.9651 mL | 19.8255 mL | 39.6511 mL |
| 5 mM | 0.793 mL | 3.9651 mL | 7.9302 mL |
| 10 mM | 0.3965 mL | 1.9826 mL | 3.9651 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。
Synthesis of new Nebularine analogues and their inhibitory activity against adenosine deaminase
Chem Pharm Bull (Tokyo) 2015;63(2):134-42.PMID:25748785DOI:10.1248/cpb.c14-00731.
A number of new 2,6-disubstituted-1-deazanebularine analogues as well as two structurally related pyrazole-fused tricyclic nucleosides were prepared. Their synthesis was carried out by the conversion of 6-amino-2-picoline to a suitable 1-deazapurine, followed by a Vorbrüggen type glycosylation and subsequent elaboration of the condensed pyrazole ring. The synthesized Nebularine analogues proved to be weak adenosine deaminase inhibitors.
Nebularine (9-2'-deoxy-beta-D-ribofuranosylpurine) has the template characteristics of adenine in vivo and in vitro
Mutat Res 1997 Jul 3;377(2):263-8.PMID:9247623DOI:10.1016/s0027-5107(97)00084-5.
Nebularine (9-beta-D-ribofuranosylpurine; Nb) is a naturally occurring nucleoside with structural features suggestive of a universal base. However, previous observations based on thermal melting characteristics of oligonucleotides suggested that Nb formed stable pairs only with thymine. To determine the template characteristics of Nb, we constructed M13 viral single-stranded DNA (ssDNA) molecules bearing a single site-specific deoxynebularine (9-2'-deoxy-beta-D-ribofuranosylpurine) residue. The ssDNA constructs were transfected into Escherichia coli cells to determine the specificity of base insertion opposite Nb, as well as to determine the effect of Nb on the replicability of the transfected DNA. Base insertion opposite Nb, analyzed by a multiplex sequencing technology, suggests that Nb has the template characteristics of adenine. Analysis of DNA replicability, measured as transfection efficiency, indicates that Nb does not block DNA replication. UV irradiation of host cells before transfection did not significantly affect survival or base insertion specificity within the limits of multiplex sequencing technology employed, suggesting that inducible mutagenic phenomena appear to have only minor effects on translesion synthesis across Nb. In addition, in vitro DNA elongation experiments on oligonucleotide templates using E. coli DNA polymerase I (Klenow fragment) as the model polymerase showed that Nb templates for T, but not for other bases under the tested conditions. The data reported in this communication underscore the importance of base-pair geometry as a specificity-determinant during base insertion by replicative polymerases.
Protection of mice against lethal dosages of Nebularine by nitrobenzylthioinosine, an inhibitor of nucleoside transport
Cancer Res 1979 Sep;39(9):3607-11.PMID:476687doi
In the presence of nitrobenzylthioinosine (NBMPR) a potent inhibitor of nucleoside transport, Roswell Park Memorial Institute 6410 cells proliferating in culture were protected from otherwise inhibitory concentrations of 9-beta-D-ribofuranosylpurine (Nebularine); cellular uptake of Nebularine was greatly reduced under these circumstances. Initial rates of Nebularine uptake by Roswell Park Memorial Institute 6410 cells were inhibited by NBMPR, indicating that the latter interfered with Nebularine transport. NBMPR protected mice against potentially lethal treatment regimens with Nebularine, 4-amino-7-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (tubercidin) or 4-amino-5-cyano-7-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (toyocamycin); protection resulted when NBMPR was administered i.p. in advance of or simultaneously with Nebularine, but not when NBMPR followed Nebularine by 1 hr. Both NBMPR and its 5'-monophosphate protected mice against Nebularine lethality when administered s.c.
Therapy of mouse leukemia L1210 with combinations of Nebularine and nitrobenzylthioinosine 5'-monophosphate
Cancer Res 1981 Feb;41(2):560-5.PMID:7448803doi
Earlier reports from this laboratory showed that: (a) in the presence of nitrobenzylthioinosine (NBMPR), a potent, tightly bound inhibitor of nucleoside transport, cells proliferating in culture were protected against a number of cytotoxic nucleosides; and (b) mice were protected against potentially lethal dosages of Nebularine (and other toxic nucleosides) by coadministration of NBMPR. The present study, which used nitrobenzylthioinosine 5'-phosphate (NBMPR-P), a readily soluble "prodrug" form of NBMPR, extended the in vivo protection studies and showed that the half-life of the protection effect was about 4 hr. In chemotherapy experiments, mice bearing transplanted neoplasms were treated with high dosages of Nebularine together with protecting doses of NBMPR-P. When mice bearing leukemia L1010 were treated with a potentially lethal regimen of Nebularine administered together with NBMPR-P, a substantial kill of leukemic cells resulted (some mice were long-term survivors). The therapeutic effect was optimal at dosage levels of the protecting agent in excess of those required in nonleukemic mice for protection against the lethal Nebularine dosages used, suggesting that the therapeutic effect was due to the joint presence in the leukemic cells of a metabolite of NBMPR-P and Nebularine; NBMPR-P protection of the leukemic host against Nebularine lethality was necessary for the therapeutic effect to be manifested.
Oligonucleotide duplexes containing inosine, 7-deazainosine, tubercidin, Nebularine and 7-deazanebularine as substrates for restriction endonucleases HindII, SalI and TaqI
Nucleic Acids Res 1986 Aug 26;14(16):6579-90.PMID:3018674DOI:10.1093/nar/14.16.6579.
Synthetic hexadecanucleotide duplexes containing a single purine nucleotide analogue in the recognition sites of the restriction endonucleases HindII, SalI and TaqI were used to investigate the restriction site determinants required by these enzymes for sequence recognition and phosphodiester bond cleavage. The enzymes were, in general, unaffected by changes introduced into the minor groove of the helix. SalI was found to be inhibited by the major groove modifications introduced into the fourth position of its recognition sequence GTCGAC. HindII and TaqI were, by contrast, able to cleave the sites containing the analogues at this position. TaqI and, to a lesser extent, HindII could also be shown to tolerate "mismatch analogues" at this site.