Resiquimod

Resiquimod, also known as R-848; S-28463; VML-600, is a n imidazoquinolinamine Toll-like receptor (TLR) agonist with potential immunostimulatory activity. Resiquimod binds to and activates TLRs 7 and 8, mainly on dendritic cells (DCs), macrophages, and B-lymphocytes, which results in the activation of the TLR signaling pathway and nuclear translocation of the transcription activator NF-kB another transcription factors; subsequently, the production of cytokines, especially interferon-alpha (INF-a), increases, enhancing T-helper 1 (Th1) immune responses. In addition, topical application of resiquimod appears to activate Langerhans cells, which may result in enhanced activation of T-lymphocytes.

Product information

CAS Number: 144875-48-9

Molecular Weight: 314.38

Formula: C17H22N4O2

Synonym:

VML-600

VML 600

VML600

S-28463

S 28463

S28463

R-848

R 848

R848

Resiquimod

Chemical Name:  1-(4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol.

Smiles: CCOCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CC(C)(C)O

InChiKey: BXNMTOQRYBFHNZ-UHFFFAOYSA-N

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)

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO, not in water

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

How to use

In Vitro:

Resiquimod (R-848) induces both hapten- and allergen-specific circulating T cells, including TH2 effectors, to produce IFN-γ and even to lose the ability to produce IL-4. Resiquimod (R848) enhances PBL proliferation in a dose-dependent manner, and increases the number of BrdU-positive cells in BrdU incorporation assay. Cells treated with R848 exhibits significantly increased (3.5-fold) luciferase (a reporter of NF-κB activity) activity.

In Vivo:

Resiquimod (R-848) (50 μg/bird, i.m. route) significantly up-regulates the expression of IFN-α, IFN-β, IFN-γ, IL-1β, IL-4, iNOS and MHC-II genes in SPF chicken.

References:

1. Sabado RL, Pavlick A, Gnjatic S, Cruz CM, Vengco I, Hasan F, Spadaccia M, Darvishian F, Chiriboga L, Holman RM, Escalon J, Muren C, Escano C, Yepes E, Sharpe D, Vasilakos JP, Rolnitzsky L, Goldberg JD, Mandeli J, Adams S, Jungbluth A, Pan L, Venhaus R, Ott PA, Bhardwaj N. Resiquimod as an Immunologic Adjuvant for NY-ESO-1 Protein Vaccination in Patients with High-Risk Melanoma. Cancer Immunol Res. 2015 Jan 29. [Epub ahead of print] PubMed PMID: 25633712.
2. Ramakrishnan S, Annamalai A, Sachan S, Kumar A, Sharma BK, Govindaraj E, Chellappa MM, Dey S, Krishnaswamy N. Synergy of lipopolysaccharide and resiquimod on type I interferon, pro-inflammatory cytokine, Th1 and Th2 response in chicken peripheral blood mononuclear cells. Mol Immunol. 2015 Mar;64(1):177-82. doi: 10.1016/j.molimm.2014.11.013. Epub 2014 Dec 9. PubMed PMID: 25500018.
3. Craft N, Birnbaum R, Quanquin N, Erfe MC, Quant C, Haskell J, Bruhn KW. Topical resiquimod protects against visceral infection with Leishmania infantum chagasi in mice. Clin Vaccine Immunol. 2014 Sep;21(9):1314-22. doi: 10.1128/CVI.00338-14. Epub 2014 Jul 16. PubMed PMID: 25030052; PubMed Central PMCID: PMC4178562.
4. Lee M, Park CS, Lee YR, Im SA, Song S, Lee CK. Resiquimod, a TLR7/8 agonist, promotes differentiation of myeloid-derived suppressor cells into macrophages and dendritic cells. Arch Pharm Res. 2014 Sep;37(9):1234-40. doi: 10.1007/s12272-014-0379-4. Epub 2014 Apr 19. PubMed PMID: 24748512.
5. Mark KE, Spruance S, Kinghorn GR, Sacks SL, Slade HB, Meng TC, Selke S, Magaret A, Wald A. Three phase III randomized controlled trials of topical resiquimod 0.01-percent gel to reduce anogenital herpes recurrences. Antimicrob Agents Chemother. 2014 Sep;58(9):5016-23. doi: 10.1128/AAC.00077-14. Epub 2014 Apr 7. PubMed PMID: 24709264; PubMed Central PMCID: PMC4135828.
6. Zhou CX, Li D, Chen YL, Lu ZJ, Sun P, Cao YM, Bao HF, Fu YF, Li PH, Bai XW, Xie BX, Liu ZX. Resiquimod and polyinosinic-polycytidylic acid formulation with aluminum hydroxide as an adjuvant for foot-and-mouth disease vaccine. BMC Vet Res. 2014 Jan 3;10:2. doi: 10.1186/1746-6148-10-2. PubMed PMID: 24386990; PubMed Central PMCID: PMC3892093.
7. Peine KJ, Gupta G, Brackman DJ, Papenfuss TL, Ainslie KM, Satoskar AR, Bachelder EM. Liposomal resiquimod for the treatment of Leishmania donovani infection. J Antimicrob Chemother. 2014 Jan;69(1):168-75. doi: 10.1093/jac/dkt320. Epub 2013 Aug 16. PubMed PMID: 23956375; PubMed Central PMCID: PMC3861330.

Products are for research use only. Not for human use.