6,9-diamino-1-(6-amino-9h-purin-9-yl)-1,5,6,7,8,9-hexadeoxydecofuranuronica
SINEFUNGIN
CAS: 58944-73-3
Molecular Formula: C15H23N7O5
6,9-diamino-1-(6-amino-9h-purin-9-yl)-1,5,6,7,8,9-hexadeoxydecofuranuronica - Names and Identifiers
| Name | SINEFUNGIN |
| Synonyms | SF rp32232 SINEFUNGIN compound57926 6,7,8,9-hexadeoxy-yl)-5 5'-DEOXY-5'-(1,4-DIAMINO-4-CARBOXYBUTYL)ADENOSINE 6,9-diamino-1-(6-amino-9h-purin-9-d-glycero-alpha-l-talo-decofuranuronicaci 6,9-diamino-1-(6-amino-9h-purin-9-yl)-1,5,6,7,8,9-hexadeoxydecofuranuronica |
| CAS | 58944-73-3 |
| EINECS | 637-385-5 |
6,9-diamino-1-(6-amino-9h-purin-9-yl)-1,5,6,7,8,9-hexadeoxydecofuranuronica - Physico-chemical Properties
| Molecular Formula | C15H23N7O5 |
| Molar Mass | 381.39 |
| Density | 1.91±0.1 g/cm3(Predicted) |
| Boling Point | 783.2±70.0 °C(Predicted) |
| Specific Rotation(α) | D25 -2.61° (c = 5 in water); D23 +12 ±2° (c = 0.227 in water) |
| Solubility | H2O: soluble |
| Appearance | powder |
| Color | white to yellow |
| pKa | pKa (66% DMF): 2.9, 3.9, 8.9, 10.2(at 25℃) |
| Storage Condition | 2-8°C |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 1 month. |
| In vitro study | Sinefungin (0.5 or 1.0 μg/mL, 60 minutes) ameliorates the TGF-β1-induced increase of α-SMA and inhibits the upregulation of histone H3K4 monomethylation in renal epithelial cells and renal fibroblast cells. Western Blot Analysis Cell Line: Renal epithelial cells. Concentration: 0.5 or 1.0 μg/mL. Incubation Time: Pretreatment 60 minutes before TGF-β1 (10 ng/mL). Result: Significantly reduced TGF-β1-inducedα-SMA protein expression and inhibited H3K4me1 in a dose-dependent manner in both NRK-52E and NRK-49F cells. |
| In vivo study | Sinefungin (10 mg/kg, per day immediately after UUO) ameliorates renal fibrosis in obstructive nephropathy. Animal Model: Male C57BL/6J mice (8 weeks of age). Dosage: 10 mg/kg Administration: Administered intraperitoneally per day immediately after UUO (prepared as a suspension in distilled water and 0.9% NaCl solution). Result: Inhibited α-SMA protein expression. Ameliorated those (α-SMA, FSP-1, collagen 1, collagen 3) both at 3 and 7 days after UUO. |
6,9-diamino-1-(6-amino-9h-purin-9-yl)-1,5,6,7,8,9-hexadeoxydecofuranuronica - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | 36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | HE3140000 |
| HS Code | 29419090 |
| Toxicity | LD50 s.c. in mice: 185 mg/kg (Hamill, Hoehn, J. Antibiot.) |
6,9-diamino-1-(6-amino-9h-purin-9-yl)-1,5,6,7,8,9-hexadeoxydecofuranuronica - Reference Information
| adenosine derivative | cenafengin (9,sinefungin) is a kind of adenosine derivative, which belongs to pan-methyltransferase inhibitor, it was originally isolated from Streptomyces griseus as a potential antifungal agent. Hercik et al. reported the crystal structure of the complex of dinafenin and ZIKV methyltransferase. SAM is a natural substrate for MTase, and xinafenin is a competitive inhibitor thereof. In combination with GTP and GDP analogs, it is possible to enhance the affinity of these analogs for enzymes, resulting in better selectivity and greater inhibition of ZIKV replication. However, when it was tested as an antiparasitic agent in dogs and goats, it was found to be toxic, which hindered its clinical use. |
| biological activity | Sinefungin is Virus particle mRNA (guanine -7-)-methyltransferase, potent inhibitors of mRNA (nucleoside -2 '-)-methyltransferase and Virus proliferation. Sinefungin is a SET7/9 inhibitor that improves renal fibrosis by inhibiting H3K4 methylation. |
| in vitro study | Sinefungin (0.5 or 1.0 μg/mL, 60 minutes) ameriorates the TGF-β1-induced increase of alpha-SMA and inhibit the upreguation of histone H3K4 monomer in renal epithetical cells and regional blast cells. Western Blot Analysis Cell Line: Renal epigenetic cells. Concentration: 0.5 or 1.0 μg/mL. TGF-β1 (10 ng/mL). Result: Significantly reduced TGF-β1-inducedα-SMA protein expression and inhibited H3K4me1 in a dose-dependent manner in both NRK-52E and NRK-49F cells. |
| Cell Line: | Renal epithelial cells. |
| Concentration: | 0.5 or 1.0 μg/mL. |
| Incubation Time: | Pretreatment 60 minutes before TGF-β1 (10 ng/mL). |
| Result: | Significantly reduced TGF-β1-inducedα-SMA protein expression and inhibited H3K4me1 in a dose-dependent manner in both NRK-52E and NRK-49F cells. Inhibited α-SMA protein expression. Ameliorated those (α-SMA, FSP-1, collagen 1, collagen 3) both at 3 and 7 days after UUO. |
| in vivo study | Sinefungin (10 mg/kg, per day after UUO) ameriorates renal fibrosis in objective nephpathy. Animal Model: Male C57BL/6J mice (8 weeks of age). Dosage: 10 mg/kg Administration: administrable intrapastrically per day after UUO (prepared as a suspension in distilled water and 0.9% NaCl solution). Result: Inhibited α-SMA protein expression. Ameliorated those (α-SMA, FSP-1, collagen 1, collagen 3) both at 3 and 7 days after UUO. |
| Animal Model: | Male C57BL/6J mice (8 weeks of age). |
| Dosage: | 10 mg/kg |
| Administration: | Administered intraperitoneally per day immediately after UUO (prepared as a suspension in distilled water and 0.9% NaCl solution). |
Last Update：2024-04-09 20:52:54
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CAS: 58944-73-3
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