Oxanosine
(Synonyms: NSC 359452) 目录号 : GC49073
A guanosine analog with diverse biological activities
Cas No.:80394-72-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >90.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Oxanosine is an analog of guanosine that has been found in S. capreolus and has diverse biological activities, including antibacterial, antiviral, and anticancer properties.1,2 It is active against a variety of bacteria, including S. flexneri, P. mirabilis, and E. coli (MICs = 6.25, 12.5, 25 µg/ml, respectively, on peptone, but not nutrient, agar). Oxanosine inhibits replication of the HIV-1 strain IIIb in infected CEM and U937, but not H9, cells (EC50s = 7, 27, and >500 µg/ml, respectively).1 It also inhibits the growth of HeLa human cervical cancer cells (IC50 = 32 µg/ml) and reduces tumor growth in a murine L1210 lymphocytic leukemia model.2
1.Saito, Y., Nakamura, M., Ohno, T., et al.Syntheses of oxanosine and carbocyclic oxanosine derivatives as anti-HIV agentsJ. Antibiot. (Tokyo)53(3)309-313(2000) 2.Shimada, N., Yagisawa, N., Naganawa, H., et al.Oxanosine, a novel nucleoside from actinomycetesJ. Antibiot. (Tokyo)34(9)1216-1218(1981)
| Cas No. | 80394-72-5 | SDF | |
| 别名 | NSC 359452 | ||
| Canonical SMILES | O=C1C2=C(N=C(O1)N)N([C@@]3([H])[C@H](O)[C@H](O)[C@@H](CO)O3)C=N2 | ||
| 分子式 | C10H12N4O6 | 分子量 | 284.2 |
| 溶解度 | N/A | 储存条件 | -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 | 3.5186 mL | 17.5932 mL | 35.1865 mL |
| 5 mM | 0.7037 mL | 3.5186 mL | 7.0373 mL |
| 10 mM | 0.3519 mL | 1.7593 mL | 3.5186 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。
Oxanosine Monophosphate Is a Covalent Inhibitor of Inosine 5'-Monophosphate Dehydrogenase
Chem Res Toxicol 2019 Mar 18;32(3):456-466.PMID:30746940DOI:10.1021/acs.chemrestox.8b00342.
Reactive nitrogen species (RNS) are produced during infection and inflammation, and the effects of these agents on proteins, DNA, and lipids are well recognized. In contrast, the effects of RNS damaged metabolites are less appreciated. 5-Amino-3-β-(d-ribofuranosyl)-3 H-imidazo-[4,5- d][1,3]oxazine-7-one (Oxanosine) and its nucleotides are products of guanosine nitrosation. Here we demonstrate that Oxanosine monophosphate (OxMP) is a potent reversible competitive inhibitor of IMPDH. The value of Ki varies from 50 to 340 nM among IMPDHs from five different organisms. UV spectroscopy and X-ray crystallography indicate that OxMP forms a ring-opened covalent adduct with the active site Cys (E-OxMP*). Unlike the covalent intermediate of the normal catalytic reaction, E-OxMP* does not hydrolyze, but instead recyclizes to OxMP. IMPDH inhibitors block proliferation and can induce apoptosis, so the inhibition of IMPDH by OxMP presents another potential mechanism for RNS toxicity.
Oxanosine is a substrate of adenosine deaminase. Implications for the quest for a toxicological marker for nitrosation activity
Chem Res Toxicol 2005 Dec;18(12):1830-41.PMID:16359173DOI:10.1021/tx050232h.
Oxanosine 3r, 5-amino-3-beta-(d-ribofuranosyl)-3H-imidazo[4,5-d][1,3]oxazine-7-one, was isolated as a novel nucleoside antibiotic in 1981 from Streptomyces capreolus MG265-CF3. Oxanosine became relevant in toxicology in 1996 with the discovery that it is formed in nitrosative guanosine deamination. As part of studies of the mechanism of Oxanosine formation, the synthesis was attempted of [7- 18O]Oxanosine by enzymatic 16O/18O-exchange with adenosine deaminase (ADA) in analogy to the synthesis of [6- 18O]guanosine from 2-amino-6-chloropurine. Unexpectedly, it was discovered that the incubation of Oxanosine 3r with ADA in sodium phosphate buffer (pH = 7.4) results in 1-beta-(d-ribofuranosyl)-5-ureido-1H-imidazole-4-carboxylic acid 4r. The reaction of the 2'-deoxyribose derivative 3d forms 4d in analogy. The reaction products were separated by preparative RP-HPLC and characterized by LC/MS and MS/MS analyses and UV/vis and NMR spectroscopy, and NMR assignments were corroborated by GIAO and GIAO-PCM calculations. Reaction in H2 18O leads to 18O-incorporation at C7. The hydrolysis of 3 to 4 can be rationalized on the basis of the known mode of action of ADA, and an explanation is provided for ADA's accomplishment of the "usual" substitution at C6 of adenosine (addition to the exocyclic bond) and the "lactone hydrolysis" of Oxanosine (addition to the endocyclic double bond). The Michaelis-Menten constant of Km = 1.0 (+/-0.2) mM was measured for Oxanosine. Implications are discussed for studies of nitrosative deamination of nucleosides, nucleotides, and oligonucleotides.
Oxanosine, a novel nucleoside from actinomycetes
Nucleic Acids Symp Ser 1981;(10):55-8.PMID:7031611doi
Oxanosine, a novel nucleoside, has been isolated from the culture filtrate of a strain of Streptomyces. The structure was determined to be 5-amino-3-beta-D-ribofuranosyl-3H-imidazo [4,5-d] [1,3]oxazin-7-one by X-ray crystallographic analysis and chemical studies. Oxanosine showed weak antibacterial activity on peptone agar; for example, Escherichia coli K-12 (MIC 12.5 mcg/ml). The antibacterial activity was antagonized by addition of guanine, guanosine and 5'-guanylic acid. Oxanosine inhibited the growth of HeLa cells in vitro (IC50 32 mcg/ml) and suppressed the growth of L-1210 leukemia in mice. The primary action of Oxanosine appears to be inhibition of GMP-synthetase. Intravenous injection of 4 mg of Oxanosine to mice does not show any toxic sign.
Mode of action of Oxanosine, a novel nucleoside antibiotic
J Antibiot (Tokyo) 1982 Jun;35(6):755-9.PMID:6288649DOI:10.7164/antibiotics.35.755.
Oxanosine, a novel nucleoside, inhibits the growth of Escherichia coli K-12 on peptone agar, but not on Nutrient agar. This antibiotic activity was found to be bacteriostatic and was antagonized by guanine, guanosine, and guanylic acid. The growth of leukemia L 1210 cell was also inhibited by Oxanosine, and the inhibition was reversed by guanylic acid. Oxanosine was confirmed to be a competitive inhibitor of GMP synthetase (E.C. 6.3.5.2) and the Ki value was 7.4 X 10(-4) M.
Synergistic anti-viral effect of Oxanosine and ddI against human immunodeficiency virus
Biomed Pharmacother 2005 Jan-Feb;59(1-2):47-50.PMID:15740935DOI:10.1016/j.biopha.2004.05.017.
The combined effect against human immunodeficiency virus (HIV) of Oxanosine and 2'3'-dideoxyinosine (ddI) has been evaluated by the production of viral particles, the expression of viral antigens on cell surfaces, and the amount of viral genome integrated in the host cells. Oxanosine alone has no effect on HIV replication up to 100 microg/ml, however, in the presence of ddI, Oxanosine revealed concentration dependent inhibition against HIV without cytotoxicity.