| Identification | Back Directory | [Name]
7-ALLYL-7 8-DIHYDRO-8-OXOGUANOSINE 95 | [CAS]
121288-39-9 | [Synonyms]
RWJ 21757
Loxoribine
7,8-Dihydro-8-oxo-7-allyl-guanosine
7-ALLYL-7 8-DIHYDRO-8-OXOGUANOSINE 95
7-Allyl-7,8-dihydro-8-oxoguanosine 95%
7,8-Dihydro-8-oxo-7-(2-propenyl)guanosine
Guanosine, 7,8-dihydro-8-oxo-7-(2-propenyl)-
Guanosine, 7,8-dihydro-8-oxo-7-(2-propen-1-yl)-
7,8-dihydro-8-oxo-7-allyl-guanosine, Loxoribine
7-ALLYL-7 8-DIHYDRO-8-OXOGUANOSINE 95 USP/EP/BP
7-Allyl-7,8-dihydro-8-oxoguanosine
(Loxoribine)
7-Allyl-2-amino-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7,9-dihydro-1H-purine-6,8-dione | [Molecular Formula]
C13H17N5O6 | [MDL Number]
MFCD00867591 | [MOL File]
121288-39-9.mol | [Molecular Weight]
339.306 |
| Chemical Properties | Back Directory | [Melting point ]
227-230 °C(lit.)
| [density ]
1.92±0.1 g/cm3(Predicted) | [storage temp. ]
Desiccate at +4°C | [solubility ]
Soluble in DMSO (up to 25 mg/ml). | [form ]
White to off-white solid. | [pka]
10.29±0.20(Predicted) | [color ]
White | [Optical Rotation]
[α]21/D 32°, c = 1 in H2O | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months. |
| Hazard Information | Back Directory | [Description]
Loxoribine is a guanosine derivative and an agonist of toll-like receptor 7 (TLR7). It is selective for TLR7 over other human TLRs in a cell-based reporter assay at 1 mM.. Loxoribine induces proliferation, increases the antibody response to sheep red blood cells, and activates natural killer cell activity against Yac-1 lymphoma cells in murine splenocyte cultures (EC50s = 10-50, 3-20, and 13-22 μM, respectively). Loxoribine (250 μM) increases production of IL-12, IL-23, IL-27, and IL-10 by human monocyte-derived dendritic cells (MoDCs). Loxoribine-treated MoDCs induce higher levels of IL-17 and IFN-γ secretion by co-cultured allogeneic CD4+ T cells compared to control MoDCs. Loxoribine (120 mg/kg) reduces the number of pulmonary metastases in the B16 mouse model of melanoma, an effect enhanced by co-administration of IL-2, and exhibits adjuvant activity in mice immunized with a B16 tumor vaccine. | [Chemical Properties]
White Solid | [Uses]
7-Allyl-7,8-dihydro-8-oxoguanosine (Loxoribine) is a small-molecule immunostimulant. Loxoribine is a toll-like receptor 7 (TLR7) agonist; induces immune cell activation and increases cytokine product
ion. Loxoribine displays antitumor and antiviral activity in various animal models. | [Uses]
Small-molecule immunostimulants | [Biological Activity]
Toll-like receptor 7 (TLR7) agonist; induces immune cell activation and increases cytokine production. Displays antitumor and antiviral activity in various animal models. | [in vivo]
Loxoribine (2 mg; s.c.or i.v.) activates murine natural killer (NK) cells in vivo[3].
| Animal Model: | 8-12 weeks male CBA/J mice[3] | | Dosage: | 2 mg | | Administration: | Subcutaneous or intravenous injection | | Result: | activates murine natural killer (NK) cells in vivo. |
| [IC 50]
TLR7 | [References]
1) Heil?et al.?(2003),?The Tool-like receptor 7 (TLR7)-specific stimulus loxoribine uncovers a strong relationship within the TLR7, 8 and 9 subfamily; Eur. J. Immunol.,?33?2987
2) Goodman?et al.?(1995),?A new approach to vaccine adjuvants. Immunopotentiation by intracellular T-helper-like signals transmitted by loxoribine;?Pharm. Biotechnol.,?6?581
3) Girart?et al.?(2007), Engagement of TLR3, TLR7 and NKG2D regulate IFN-gamma secretion but not NKG2D-mediated cytotoxicity by human NK cells stimulated with suboptimal doses of IL-12; J. Immunol.,?179?3472
4) Stewart?et al.?(2012),?Toll-like receptor 7 ligands inhibit influenza A infection in chickens; J. Interferon Cytokine Res,,?32?46
5) Wang?et al.?(2015),?The TLR7 agonist induces tumor regression both by promoting CD4-T cells proliferation and by reversing T regulatory cell-mediated suppression via dendritic cells; Oncotarget,?6?1779 |
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