Loxoribine

ChemicalBook > CAS DataBase List > Loxoribine

Product Name: Loxoribine
CAS No.: 121288-39-9
Chemical Name: Loxoribine
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)-;7,8-dihydro-8-oxo-7-allyl-guanosine, Loxoribine;Guanosine, 7,8-dihydro-8-oxo-7-(2-propen-1-yl)-;7-Allyl-7,8-dihydro-8-oxoguanosine (Loxoribine)
CBNumber: CB7499469
Molecular Formula: C13H17N5O6
Formula Weight: 339.3
MOL File: 121288-39-9.mol

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Loxoribine Property

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 activity: [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.

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Safety

WGK Germany: 3
HS Code: 29349990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 496812
Product name: 7-Allyl-7,8-dihydro-8-oxoguanosine
Purity: 95%
Packaging: 50mg
Price: $82.4
Updated: 2024/03/01

Sigma-Aldrich

Product number: 496812
Product name: 7-Allyl-7,8-dihydro-8-oxoguanosine
Purity: 95%
Packaging: 250mg
Price: $192.4
Updated: 2024/03/01

Cayman Chemical

Product number: 21186
Product name: Loxoribine
Purity: ≥98%
Packaging: 5mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 21186
Product name: Loxoribine
Purity: ≥98%
Packaging: 10mg
Price: $61
Updated: 2024/03/01

Cayman Chemical

Product number: 21186
Product name: Loxoribine
Purity: ≥98%
Packaging: 25mg
Price: $86
Updated: 2024/03/01

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Loxoribine Chemical Properties,Usage,Production

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

Loxoribine is a selective toll-like receptor 7 (TLR7) agonist that activates immune cells and increases cytokine production.

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.

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

Loxoribine Preparation Products And Raw materials

Raw materials

Preparation Products

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121288-39-9, LoxoribineRelated Search:

Geldanamycin TYRPHOSTIN AG 1296 Imatinib mesylate 17-AAG 4,5-Diamino-6-hydroxypyrimidine 8-OXO-2'-DEOXYGUANOSINE 2,4-Diamino-5-(formylamino)-6-hydroxypyrimidine 2,4-Diamino-6-hydroxypyrimidine Loxoribine

7-ALLYL-7 8-DIHYDRO-8-OXOGUANOSINE 95

Loxoribine

7-Allyl-2-amino-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-7,9-dihydro-1H-purine-6,8-dione

7,8-Dihydro-8-oxo-7-(2-propenyl)guanosine

RWJ 21757

Guanosine, 7,8-dihydro-8-oxo-7-(2-propenyl)-

7-Allyl-7,8-dihydro-8-oxoguanosine 95%

7,8-Dihydro-8-oxo-7-allyl-guanosine

7-Allyl-7,8-dihydro-8-oxoguanosine (Loxoribine)

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

RWJ-21757,Loxoribine,natural,Toll-like Receptor (TLR),killer,cells,Influenza Virus,Inhibitor,cells,inhibit,TLR-7,MoDCs,RWJ21757

121288-39-9

Heterocyclic Compounds

Bases & Related Reagents

Heterocycles

Nucleotides

Nucleosides

Oligonucleotide Synthesis

Specialty Synthesis