Nebularine
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Nebularine (9-β-D-Ribofuranosylpurine) is a naturally occurring cytotoxic purine riboside antibiotic. Nebularine competitively inhibits adenine deaminase and xanthine oxidase, and acts as a template for thymine insertion during DNA elongation and replication. Nebularine serves as a cytokinin antagonist and induces mitotic aberrations in plant cells. Nebularine exhibits cytotoxicity against plants, mammals, fungal organisms and cancer cells. Nebularine can be used in research related to fungal infections, plant growth, as well as chronic myeloid leukemia, acute lymphoblastic leukemia and breast cancer.
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- Pureza: 98.44%
- No. CAS: 550-33-4
- Fòrmula: C10H12N4O4
- Peso molecular:252.23
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Almacenamiento:
Store at room temperature, keep dry and cool.
In solvent -80°C, 1 year , -20°C, 6 months
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Actividad biológica
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| L929 | IC50 |
2.37 μM
Compound: 3, Nebularine
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Cytotoxicity against mouse L929 cells assessed as cell viability after 72 hrs by WST-1 assay
Cytotoxicity against mouse L929 cells assessed as cell viability after 72 hrs by WST-1 assay
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[PMID: 24283924] |
| Vero | IC50 |
0.6 nM
Compound: Nebularine
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Anti-Herpes simplex virus type-1 activity in vero cells using plaque inhibition assay
Anti-Herpes simplex virus type-1 activity in vero cells using plaque inhibition assay
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[PMID: 10464017] |
Nebularine acts as a template to guide the insertion of thymine by the nuclease-deficient Escherichia coli DNA polymerase I Klenow fragment in vitro[1].
Nebularine (4 μM-2.0 mM; 1 week) potently inhibits the growth of seedlings of spinach, lettuce, carrot, alfalfa, snapdragon and wheat; at 2.0 mM, it inhibits the axis length, root length and aboveground fresh weight of wheat seedlings by 90%, 97% and 60%, respectively, and induces chromosomal abnormalities in root tip cells of all tested species[2].
Nebularine (2.5-20 μM; 3-36 h) acts as a cytokinin antagonist in *Amaranthus caudatus* seedlings. When its concentration is 8-fold that of cytokinins, it inhibits kinetin- or zeatin-induced betalain biosynthesis, with a maximum inhibition rate of up to 60%, and increasing kinetin concentration reverses this inhibitory effect[2].
Nebularine (20 μM; 5 days) antagonizes the green-retaining effect of kinetin in leaf segments of 7-day-old wheat seedlings; when 20 μM of this substance is present together with 2.5 μM kinetin, it reduces the activity of kinetin by 35%[2].
Nebularine (4-20 μM) acts as a non-competitive inhibitor of xanthine oxidase, and inhibits 85% of the enzyme activity at a substrate xanthine concentration of 40 μM and its own concentration of 20 μM[2].
Nebularine (72 h) potently inhibits the viability of human K562, CEM and MCF-7 cell lines, with IC50 values of 2.2 μM, 1.1 μM and 3.6 μM, respectively[3].
Nebularine (10-100 μM; 24-48 h) inhibits the viability of tobacco BY-2 cells, with an IC50 of 20 μM after 48 h of incubation[3].
Nebularine (0.067 mM) inhibits human erythrocyte adenosine deaminase ADA1 by reducing inosine production to 60%[3].
Nebularine (0.25-1 μM; 7 days) concentration-dependently shortens the primary root and promotes lateral root formation in Arabidopsis thaliana Col-0 seedlings, and also reverses the lateral root inhibition induced by 0.01 μM BAP (HY-B0941)[3].
Nebularine (10-100 μM; 6 days) antagonizes the chlorophyll retention effect of 30 μM BAP on isolated wheat leaf tips, reducing this effect to 55% after 6 days of incubation at equimolar concentrations[3].
Nebularine (1-50 μM) inhibits the growth of cytokinin-dependent tobacco calli stimulated by 1 μM BAP in a concentration-dependent manner[3].
Nebularine (10-50 μM; 16 h) reduces the expression levels of cytokinin-responsive ARR5:GUS and auxin-responsive DR5:GUS in Arabidopsis thaliana seedlings; after incubation at 10 μM or higher concentrations for 16 h, the induced expression levels are reduced to approximately 70%[3].
Nebularine (500 μg per paper disc; 2-5 days) exhibits moderate antifungal activity against Magnaporthe grisea and Trichophyton mentagrophytes, with an inhibition zone diameter of 9 mm (including the diameter of the paper disc), and shows no activity against other tested fungi and bacteria[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:tobacco BY-2 suspension cells
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Concentration:10, 50, 100 μM
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Incubation Time:24 h, 48 h
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Result:Caused over 60% cell death in 24 h at 100 μM; caused nearly complete cell death in 48 h at 100 μM.
Inhibited BY-2 cell growth with an IC50 value of 20 μM after 48 h of incubation.
Chemical Information
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No. CAS 550-33-4
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Appearance Solid
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Peso molecular 252.23
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Fòrmula C10H12N4O4
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Color White to off-white
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SMILES
OC[C@@H](O1)[C@@H](O)[C@@H](O)[C@@H]1N2C=NC3=C2N=CN=C3
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Synonyms
9-β-D-Ribofuranosylpurine
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Structure Classification
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Initial Source
Microbispora sp.
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
Store at room temperature, keep dry and cool
In solvent -80°C 1 year -20°C 6 months
Solvente y solubilidad
DMSO : 125 mg/mL (495.58 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 1 year; -20°C, 6 months. When stored at -80°C, please use it within 1 year. When stored at -20°C, please use it within 6 months.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 1 year; -20°C, 6 months. When stored at -80°C, please use it within 1 year. When stored at -20°C, please use it within 6 months.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Pureza y Documentación
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Ficha de datos (279 KB)
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SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
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Instrucciones de manejo (2659 KB)
Referencias
[1]. Rahman MSet al. 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. [Content Brief]
[4]. Kim YS, et al. Chemical Constituents of the Fruiting Bodies of Clitocybe nebularis and Their Antifungal Activity. Mycobiology. 2008 Jun;36(2):110-3. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 1 year; -20°C, 6 months. When stored at -80°C, please use it within 1 year. When stored at -20°C, please use it within 6 months.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 3.9646 mL | 19.8232 mL | 39.6464 mL | 99.1159 mL |
| 5 mM | 0.7929 mL | 3.9646 mL | 7.9293 mL | 19.8232 mL | |
| 10 mM | 0.3965 mL | 1.9823 mL | 3.9646 mL | 9.9116 mL | |
| 15 mM | 0.2643 mL | 1.3215 mL | 2.6431 mL | 6.6077 mL | |
| 20 mM | 0.1982 mL | 0.9912 mL | 1.9823 mL | 4.9558 mL | |
| 25 mM | 0.1586 mL | 0.7929 mL | 1.5859 mL | 3.9646 mL | |
| 30 mM | 0.1322 mL | 0.6608 mL | 1.3215 mL | 3.3039 mL | |
| 40 mM | 0.0991 mL | 0.4956 mL | 0.9912 mL | 2.4779 mL | |
| 50 mM | 0.0793 mL | 0.3965 mL | 0.7929 mL | 1.9823 mL | |
| 60 mM | 0.0661 mL | 0.3304 mL | 0.6608 mL | 1.6519 mL | |
| 80 mM | 0.0496 mL | 0.2478 mL | 0.4956 mL | 1.2389 mL | |
| 100 mM | 0.0396 mL | 0.1982 mL | 0.3965 mL | 0.9912 mL |
- Nebularine
- 550-33-4
- 9-β-D-Ribofuranosylpurine
- Antibiotic
- Adenosine Deaminase
- Xanthine Oxidase
- Fungal
- Bacterial
- Nucleoside Antimetabolite/Analog
- tobacco BY-2 cell line
- human MCF-7 cell line
- Magnaporthe grisea
- human CEM cell line
- xanthine oxidase
- human K562 cell line
- Arabidopsis thaliana
- adenosine deaminase
- Lepista (Clitocybe) nebularis
- Escherichia coli DNA polymerase I Klenow fragment
- Inhibitor
- inhibitor
- inhibit