Loxoribine
| Code | Size | Price |
|---|
| AG-CR1-3584-M005 | 5 mg | £40.00 |
Quantity:
| AG-CR1-3584-M025 | 25 mg | £100.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
+4°C
Documents
Further Information
Alternate Names/Synonyms:
7-Allyl-8-oxoguanosine; RWJ 21757
Appearance:
White to off-white powder.
CAS:
121288-39-9
EClass:
32160000
Form (Short):
liquid
Handling Advice:
After reconstitution, prepare aliquots and store at -20°C.Avoid freeze/thaw cycles.
InChi:
InChI=1/C13H17N5O6/c1-2-3-17-6-9(15-12(14)16-10(6)22)18(13(17)23)11-8(21)7(20)5(4-19)24-11/h2,5,7-8,11,19-21H,1,3-4H2,(H3,14,15,16,22)/t5-,7?,8?,11-/m1/s1/f/h16H,14H2
InChiKey:
VDCRFBBZFHHYGT-HKPXRNTQDL
Long Description:
Chemical. CAS: 121288-39-9. Formula: C13H17N5O6. MW: 339.3. Guanosine analog derivatized at position N7 and C8. Very potent immunostimulatory compound that increases cytokine production. Antitumor and antiviral activity compound. Potent and selective synthetic ligand for Toll-like receptor 7 (TLR7). Co-incubation with thymidine homopolymer oligodeoxynucleotides (ODN) redirected the stimulatory effect of loxoribine away from TLR7 toward TLR8. Induces autophagy and autophagy-induced cell death in Caco-2 cells. Shows adjuvant activity to increase the effectiveness of vaccines.
MDL:
MFCD00867591
Molecular Formula:
C13H17N5O6
Molecular Weight:
339.3
Package Type:
Vial
Product Description:
Guanosine analog derivatized at position N7 and C8 [1]. Very potent immunostimulatory compound that increases cytokine production [2-5]. Antitumor and antiviral activity compound [5, 6, 7, 12]. Potent and selective synthetic ligand for Toll-like receptor 7 (TLR7) [7-10]. Co-incubation with thymidine homopolymer oligodeoxynucleotides (ODN) redirected the stimulatory effect of loxoribine away from TLR7 toward TLR8 [11]. Induces autophagy and autophagy-induced cell death in Caco-2 cells [12]. Shows adjuvant activity to increase the effectiveness of vaccines [4].
Purity:
>97%
SMILES:
NC1=NC2=C(N(CC=C)C(=O)N2[C@@H]2O[C@H](CO)C(O)[C@@H]2O)C(=O)N1
Solubility Chemicals:
Soluble in DMSO (30mg/ml) or water (10mg/ml).
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C. Stock solutions are stable for at least 3 months when stored at -20°C.
References
Substituted guanine ribonucleosides as B cell activators: S. Gupta, et al.; Clin. Immunol. Immunopathol. 61, 21 (1991) | In vivo enhancement of murine natural killer cell activity by 7-allyl-8-oxoguanosine (loxoribine): B.L. Pope, et al.; Int. J. Immunopharmacol. 14, 1375 (1992) | Loxoribine (7-allyl-8-oxoguanosine) activates natural killer cells and primes cytolytic precursor cells for activation by IL-2: B.L. Pope, et al.; J. Immunol. 151, 3007 (1993) | 7-Allyl-8-oxoguanosine (loxoribine) inhibits the metastasis of B16 melanoma cells and has adjuvant activity in mice immunized with a B16 tumor vaccine: B.L. Pope, et al.; Cancer Immunol. Immunother. 38, 83 (1994) | The immunostimulatory compound 7-allyl-8-oxoguanosine (loxoribine) induces a distinct subset of murine cytokines: B.L. Pope, et al.; Cell Immunol. 162, 333 (1995) | Phase 1, randomized, double-blind trial of 7-allyl-8-oxoguanosine (loxoribine) in advanced cancer: S.S. Agarwala, et al.; Cytokines Cell Mol. Ther. 6, 171 (2000) | Recognition of pathogen-associated molecular patterns by TLR family: S. Akira & H. Hemmi; Immunol. Lett. 85, 85 (2003) (Review) | The Toll-like receptor 7 (TLR7)-specific stimulus loxoribine uncovers a strong relationship within the TLR7, 8 and 9 subfamily: F. Heil, et al.; Eur. J. Immunol. 33, 2987 (2003) | Synthetic TLR agonists reveal functional differences between human TLR7 and TLR8: K.B. Gorden, et al.; J. Immunol. 174,1259 (2005) | Intervention of Toll-like receptor-mediated human innate immunity and inflammation by synthetic compounds and naturally occurring products: S. Fasciano & L. Li; Curr. Med. Chem. 13, 1389 (2006) (Review) | Modulating responsiveness of human TLR7 and 8 to small molecule ligands with T-rich phosphorothiate oligodeoxynucleotides: M. Jurk, et al.; Eur. J. Immunol. 36, 1815 (2006) | Autophagy-mediated anti-tumoral activity of imiquimod in Caco-2 cells: J.Y. Yi, et al.; BBRC 386, 455 (2009) | Loxoribine, a selective Toll-like receptor 7 agonist, induces maturation of human monocyte-derived dendritic cells and stimulates their Th-1- and Th-17-polarizing capability: T. Dzopalic, et al.; Int. Immunopharmacol. 10, 1428 (2010) | TLR7 agonists display potent antiviral effects against norovirus infection via innate stimulation: D.E. Tuipulotu, et al.; Antimicrob. Agents Chemother. 62, e02417 (2018) | Possible role of intravenous administration of mesenchymal stem cells to alleviate interstitial cystitis/bladder pain syndrome in a Toll-like receptor-7 agonist-induced experimental animal model in rat: H. Tabata, et al.; BMC Urology 21, 156 (2021)
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