RESIQUIMOD Chemical Properties

Melting point:

190-193°

Boiling point:

553.6±50.0 °C(Predicted)

Density 

1.28

storage temp. 

-20°C

solubility 

DMSO: soluble10mg/mL, clear (warmed to 60 °C)

form 

powder

pka

14.63±0.29(Predicted)

color 

white to tan

λmax

325nm(lit.)

Merck 

14,8151

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.

InChI

InChI=1S/C17H22N4O2/c1-4-23-9-13-20-14-15(21(13)10-17(2,3)22)11-7-5-6-8-12(11)19-16(14)18/h5-8,22H,4,9-10H2,1-3H3,(H2,18,19)

InChIKey

BXNMTOQRYBFHNZ-UHFFFAOYSA-N

SMILES

C12=C(C(=NC3C=CC=CC1=3)N)N=C(COCC)N2CC(O)(C)C

Safety Information

WGK Germany 

3

RTECS 

NJ5911320

HS Code 

2933998090

RESIQUIMOD Usage And Synthesis

Description

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

Uses

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.

Uses

Resiquimod has been used in the stimulation of bone marrow-derived dendritic cells (BMDCs) stimulation( and B cells. It has also been used as a ligand for toll-like receptors (TLR7) in malignant melanoma cell line B16F10.

Definition

ChEBI: Resiquimod is an imidazoquinoline.

Biochem/physiol Actions

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.

Synthesis

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).

storage

Store at +4°C

References

[1] MARION JURK. Human TLR7 or TLR8 independently confer responsiveness to the antiviral compound R-848[J]. Nature Immunology, 2002, 3 6: 499-499. DOI:10.1038/ni0602-499
[2] RACHEL LUBONG SABADO. Resiquimod as an immunologic adjuvant for NY-ESO-1 protein vaccination in patients with high-risk melanoma.[J]. Cancer immunology research, 2015, 3 3: 278-287. DOI:10.1158/2326-6066.cir-14-0202
[3] PETR O. ILYINSKII . Adjuvant-carrying synthetic vaccine particles augment the immune response to encapsulated antigen and exhibit strong local immune activation without inducing systemic cytokine release[J]. Vaccine, 2014, 32 24: Pages 2882-2895. DOI:10.1016/j.vaccine.2014.02.027
[4] MAKI YOKOGAWA. Epicutaneous Application of Toll-like Receptor 7 Agonists Leads to Systemic Autoimmunity in Wild-Type Mice: A New Model of Systemic Lupus Erythematosus[J]. Arthritis & Rheumatology, 2013, 66 3: 694-706. DOI:10.1002/art.38298
[5] DANIEL ENOSI TUIPULOTU. TLR7 Agonists Display Potent Antiviral Effects against Norovirus Infection via Innate Stimulation.[J]. Antimicrobial Agents and Chemotherapy, 2018. DOI:10.1128/aac.02417-17

RESIQUIMOD(144875-48-9)Related Product Information

• Retinoic acid
• Sunitinib Malate
• Zafirlukast
• Etoposide
• GLYX 13
• Imiquimod
• 5-AZABENZIMIDAZOLE
• 3H-IMIDAZO[4,5-C]PYRIDINE
• 2-METHYLIMIDAZO[4,5-C]PYRIDINE
• RESIQUIMOD
• 1-(2-METHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLINE
• 4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline
• 1H-Imidazo[4,5-c]pyridine,1-ethyl-