144875-48-9

Resiquimod (CAS 144875-48-9) is a Toll-like receptor 7/8 agonist.1 May be used as an immune adjuvant in cancer vaccines.2 Resiquimod-carrying synthetic vaccine particles augment the immune response to encapsulated antigen and exhibit strong local immune activation without inducing systemic cytokine release.3 Topical treatment of wild-type mice induces systemic autoimmune disease which may be used as a model of systemic Lupus erythematosus.4? It displayed potent antiviral activity (EC50 = 23.5 nM) in a murine norovirus replicon model.5

Resiquimod is an imidazoquinoline derivative that acts as an immune response modifier. Resiquimod shows antitumor and antiviral activity and is used in the treatment of skin lesions such as herpes simplex virus. Resiquimod is a toll-like receptor 9 (TLR7) agonist.

ChEBI: Resiquimod is an imidazoquinoline.

R-848 is a selective ligand for Toll-like receptor 7 (TLR7) in mouse and for TLR7 and TLR8 in human. Potent antitumor and antiviral compound. Stimulates antibody secretion, cytokine production, protection from apoptosis and CD80 upregulation.

Resiquimod belongs to the class of imidazoquinolinamines compounds with immunomodulatory effects. Resiquimod increases the levels of cytokines such as TNF-α, IL-6 and IFN-α.

Preparation of R-848: A mixture of 2-amino-2-methyl-1-propanol (1.87 g, 5.3 mmol) and methanol was placed in an autoclave, sealed and then the reaction was stirred at 160 °C for 8 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/triethylamine=95:5) to finally obtain the target product R-848 (1.5 g).

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1) Jurk et al. (2002), Human TLR7 or TLR8 independently confer responsiveness to the antiviral compound R-848; Nat. Immunol., 3 499 2) Sabado et al. (2015), Resiquimod as an immunologic adjuvant for NY-ESO-1 protein vaccination in patients with high-risk melanoma; Cancer Immunol. Res., 3 278 3) Ilyinskii et al. (2014), Adjuvant-carrying synthetic vaccine particles augment the immune response to encapsulated antigen and exhibit strong local immune activation without inducing systemic cytokine release; Vaccine, 32 2882 4) Yokogawa et al. (2014), Epicutaneous application of toll-like receptor 7 agonists leads to systemic autoimmunity in wild-type mice: a new model of systemic Lupus erthematosus; Arthritis Rheumatol., 66 694 5) Tuipulotu et al. (2018), TLR7 Agonists Display Potent Antiviral Effects against Norovirus Infection via Innate Stimulation; Antimicrob. Agents Chemother., 62 e02417