Loxoribine

CHF 40.00
In stock
AG-CR1-3584-M0055 mgCHF 40.00
AG-CR1-3584-M02525 mgCHF 120.00
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Product Details
Synonyms 7-Allyl-8-oxoguanosine; RWJ 21757
Product Type Chemical
Properties
Formula

C13H17N5O6

MW 339.3
CAS 121288-39-9
Purity Chemicals ≥97%
Appearance White to off-white powder.
Solubility Soluble in DMSO (30mg/ml) or water (10mg/ml).
InChi Key VDCRFBBZFHHYGT-HKPXRNTQDL
Smiles NC1=NC2=C(N(CC=C)C(=O)N2[C@@H]2O[C@H](CO)C(O)[C@@H]2O)C(=O)N1
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice After reconstitution, prepare aliquots and store at -20°C.
Avoid freeze/thaw cycles.
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.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • 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].
Product References
  1. Substituted guanine ribonucleosides as B cell activators: S. Gupta, et al.; Clin. Immunol. Immunopathol. 61, 21 (1991)
  2. 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)
  3. 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)
  4. 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)
  5. 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)
  6. 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)
  7. Recognition of pathogen-associated molecular patterns by TLR family: S. Akira & H. Hemmi; Immunol. Lett. 85, 85 (2003) (Review)
  8. 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)
  9. Synthetic TLR agonists reveal functional differences between human TLR7 and TLR8: K.B. Gorden, et al.; J. Immunol. 174,1259 (2005)
  10. 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)
  11. 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)
  12. Autophagy-mediated anti-tumoral activity of imiquimod in Caco-2 cells: J.Y. Yi, et al.; BBRC 386, 455 (2009)
  13. 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)
  14. TLR7 agonists display potent antiviral effects against norovirus infection via innate stimulation: D.E. Tuipulotu, et al.; Antimicrob. Agents Chemother. 62, e02417 (2018)
  15. 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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