| Identification | Back Directory | [Name]
2'-C-Methyladenosine | [CAS]
15397-12-3 | [Synonyms]
-C-Methyladenosine
2'-C-Methyladenosine
2'-CMethyl-D-adenosine
2’-β-C-Methyladenosine
Adenosine, 2'-C-methyl-
2'-C-Methyladenosine USP/EP/BP
6-Amino-9-(2'-C-methyl-b-D-ribofuranosyl)purine
2-(6-AMINOPURIN-9-YL)-5-(HYDROXYMETHYL)-3-METHYLOXOLANE-3,4-DIOL
(2R,3R,4R,5R)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)-3-methyltetrahydrofuran-3,4-diol | [Molecular Formula]
C11H15N5O4 | [MDL Number]
MFCD02682944 | [MOL File]
15397-12-3.mol | [Molecular Weight]
281.27 |
| Chemical Properties | Back Directory | [Boiling point ]
643.4±65.0 °C(Predicted) | [density ]
1.89 | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 5 mg/mL; DMSO: 20 mg/mL; PBS (pH 7.2): 10 mg/mL | [form ]
A crystalline solid | [pka]
13.18±0.70(Predicted) | [color ]
White to off-white | [InChI]
InChI=1S/C11H15N5O4/c1-11(19)7(18)5(2-17)20-10(11)16-4-15-6-8(12)13-3-14-9(6)16/h3-5,7,10,17-19H,2H2,1H3,(H2,12,13,14)/t5-,7-,10-,11-/m1/s1 | [InChIKey]
PASOFFRBGIVJET-YRKGHMEHSA-N | [SMILES]
OC[C@H]1O[C@@H](N2C3C(=C(N=CN=3)N)N=C2)[C@](C)(O)[C@@H]1O |
| Hazard Information | Back Directory | [Description]
2′-C-Methyladenosine has been shown to inhibit HCV RNA replication in the absence of cytotoxicity. The corresponding triphosphates were shown to be potent, competitive inhibitors of NS5B-catalyzed reactions in vitro. | [Uses]
2'-C-Methyladenosine is an inhibitor of hepatitis C virus (HCV) replication. 2'-C-Methyladenosine inhibits HCV replicon and NS5B-catalyzed RNA synthesis with IC50 values of 0.3μM and 1.9 μM, respectively. 2'-C-Methyladenosine also potently inhibits LRV1 in Leishmania guyanensis (Lgy) and Leishmania braziliensis[1][2]. | [Biological Activity]
2’-C-Methyladenosine is an inhibitor of hepatitis C virus (HCV) replication (IC50 = 0.3 μM in Huh-7 human hepatoma cells) that is not cytotoxic at concentrations up to 100 μM.{39652} It is converted intracellularly to adenosine triphosphate, which inhibits the RNA-dependent RNA polymerase nonstructural protein 5B (NS5B). It also inhibits growth of L. guyanensis in vitro (EC50 = 3 μM) and eradicates it when used at a concentration of 10 μM. | [Synthesis]
Synthesis of yfl-2'-methyl-adenosine (CHCl); N6-tert-butanoyl-/?-2'-methyl-2',3',5'-tribenzoyl-adenosine (400 mg, 0.590 mmol) was added to a solution of MeOH saturated with ammonia, and stirred at room temperature. After 12 hours the solvent was removed and the obtained solid was purified by column chromatography in gradient starting with a mixture of CHCl3/MeOH 9:1 then 8:2. The pure product was obtained as a white solid (120 mg, 0.427 mmol, 72%). |?H (J6-DMSO): 8.47 (IH, s, H8-adenosine), 8.15 (IH, s, H2-adenosine), 7.30 (IH, s, NH26-adenosine), 5.95 (IH, s, Hl '-adenosine), 5.25-5.21 (3H, m, OH5' -adenosine, OH3'- adenosine, OH2' -adenosine), 4.12-4.05 (IH, d, H3 '-adenosine, J= 8.6 Hz), 3.91 (IH, m, H4'-adenosine), 3.84 (IH, m, H5' -adenosine), 3.70 (IH, m, H5' -adenosine), 0.77 (3H3 s, CH32'-adenosine); |?c (4-DMSO): 156.02 (1C, C6-adenosine), 152.53 (1C, C2-adenosine), 149.01 (1C, C4-adenosine), 138.68 (1C, C8-adenosine), 118.67 (1C, C5-adenosine), 90.78 (1C, Cl '-adenosine), 82.52 (1C, C4' -adenosine), 78.46 (1C, C2'-adenosine), 71.63 (1C, C3' -adenosine), 59.47 (1C, C5 '-adenosine), 19.83 (1C, CH3-2'-adenosine). Anal. CaIc. for C11H15N5O4: C 46.97%, H 5.38%, N 24.90%. Found: C 46.67%, H 5.22%, N 24.20%. | [in vivo]
2'-C-Methyladenosine has inhibitory potency for HCV replicon in HB110A cells with an IC50 values of 0.3μM[1].
?
2'-C-Methyladenosine inhibits NS5B-catalyzed RNA synthesis with an IC50 values of 1.9 μM[1].
?
2′-C-methyladenosine potently inhibits LRV1 in Leishmania guyanensis (Lgy) and Leishmania braziliensis[2] | [storage]
Store at -20°C | [References]
[1] Steven S Carroll, et al. Inhibition of hepatitis C virus RNA replication by 2'-modified nucleoside analogs. J Biol Chem. 2003 Apr 4;278(14):11979-84. DOI:10.1074/jbc.M210914200
[2] John I Robinson, et al. Concentration of 2'C-methyladenosine triphosphate by Leishmania guyanensis enables specific inhibition of Leishmania RNA virus 1 via its RNA polymerase. J Biol Chem. 2018 Apr 27;293(17):6460-6469. DOI:10.1074/jbc.RA117.001515 |
|
| Company Name: |
T&W GROUP
|
| Telephone: |
021-61551611 13296011611 |
| Website: |
www.trustwe.com/ |
| Company Name: |
Finetech Industry Limited
|
| Telephone: |
+86-27-8746-5837 +86-18627785180 |
| Website: |
https://www.finetechnology-ind.com/ |
| Company Name: |
NewCan Biotech Limited
|
| Telephone: |
+86-571-86912261 19975279805 |
| Website: |
https://www.newcanbio.com/ |
|