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ProductsBack/Loxoribine [121288-39-9]
Chemical Structure
Chemical Structure
Chemical Structure

Loxoribine [121288-39-9]

Research Use Only
AG-CR1-3584
AdipoGen Life Sciences
CAS Number121288-39-9
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Product group Chemicals
Estimated Purity>97%
Molecular Weight339.3
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Loxoribine [121288-39-9]
  • Delivery Days Customer
    10
  • CAS Number
    121288-39-9
  • Certification
    Research Use Only
  • Estimated Purity
    >97%
  • Hazard Information
    Non-hazardous
  • Molecular Formula
    C13H17N5O6
  • Molecular Weight
    339.3
  • Scientific 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. - 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].
  • SMILES
    NC1=NC2=C(N(CC=C)C(=O)N2[C@@H]2O[C@H](CO)C(O)[C@@H]2O)C(=O)N1
  • Storage Instruction
    2°C to 8°C,-20°C
  • UNSPSC
    12352200

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)