Stock solutions of Resiquimod in DMSO or ethanol may be stored at -20°C for a maximum duration of 2 months.
SML0196
Resiquimod
≥98% (HPLC), powder, TLR7/TLR8 agonist
Synonym(s):
4-Amino-2-(ethoxymethyl)-alpha, R-848, R848, S28463, alpha-dimethyl-1H-imidazo(4,5-c)quinoline-1-ethanol
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About This Item
Empirical Formula (Hill Notation):
C17H22N4O2
CAS Number:
Molecular Weight:
314.38
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
MDL number:
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Product Name
Resiquimod, ≥98% (HPLC)
SMILES string
CCOCc1nc2c(N)nc3ccccc3c2n1CC(C)(C)O
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)
InChI key
BXNMTOQRYBFHNZ-UHFFFAOYSA-N
assay
≥98% (HPLC)
form
powder
storage condition
desiccated
protect from light
color
white to tan
solubility
DMSO: 10 mg/mL, clear (warmed to 60 °C)
shipped in
wet ice
storage temp.
−20°C
Quality Level
Related Categories
1 of 4
This Item | SML0877 | 401020 | SML1406 |
|---|---|---|---|
| assay ≥98% (HPLC) | assay ≥98% (HPLC) | assay ≥98% (HPLC) | assay ≥98% (HPLC) |
| form powder | form powder | form solid | form powder |
| Quality Level 100 | Quality Level 100 | Quality Level 100 | Quality Level 100 |
| storage temp. −20°C | storage temp. −20°C | storage temp. 2-8°C | storage temp. 2-8°C |
| solubility DMSO: 10 mg/mL, clear (warmed to 60 °C) | solubility DMSO: 10 mg/mL, clear | solubility DMSO: 3 mg/mL | solubility DMSO: 5 mg/mL, clear (warmed) |
| storage condition desiccated, protect from light | storage condition - | storage condition OK to freeze, protect from light | storage condition - |
Application
Resiquimod has been used in the stimulation of bone marrow-derived dendritic cells (BMDCs) stimulation([1] and B cells.[2] It has also been used as a ligand for toll-like receptors (TLR7) in malignant melanoma cell line B16F10.[3][4]
Resiquimod may be used in immunological and cancer-related cell signaling studies.
Biochem/physiol Actions
Resiquimod (R-848) is a potent synthetic agonist of TLR7/TLR8 that possesses antiviral and antitumoral activities.
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.[5][6]
Resiquimod is 314.4 Da molecule which elicits immune function during visceral infection with L. infantum Sp. It mediates the trafficking of granulocytes, macrophages, leukocytes and dendritic cells.[7] It is a recommended topical drug for treating skin tumors like actinic keratosis (AK) and superficial basal cell carcinoma.[8]
Resiquimod is an agonist of toll-like receptor 7 and 8 (TLR- and TLR-8).
Features and Benefits
This compound is featured on the Cytokine Receptors (Interleukin-1 Receptor/TIR Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Bridget Freyne et al.
The Journal of infectious diseases, 217(11), 1798-1808 (2018-02-08)
BCG vaccination is associated with a reduction in all-cause infant mortality in high-mortality settings. The underlying mechanisms remain uncertain, but long-term modulation of the innate immune response (trained immunity) may be involved. Whole-blood specimens, collected 7 days after randomization from
AMPK Promotes Xenophagy through Priming of Autophagic Kinases upon Detection of Bacterial Outer Membrane Vesicles
Losier TT, et al.
Cell Reports, 26(8), 2150-2165 (2019)
D H Dockrell et al.
The Journal of antimicrobial chemotherapy, 48(6), 751-755 (2001-12-06)
Augmenting the host's natural immune response to viruses by the administration of exogenous cytokines such as interferon-alpha (IFN-alpha) is a strategy increasingly employed in antiviral therapeutics. Enhancing the release of endogenous cytokines is, however, an alternative approach. The imidazoquinolinamines imiquimod
Resiquimod, a topical drug for viral skin lesions and skin cancer
Meyer T, et al.
Expert Opinion on Investigational Drugs, 22(1), 149-159 (2013)
Suppression of innate and adaptive B cell activation pathways by antibody coengagement of FcgammaRIIb and CD19
Szili,D, et al.
MAbs, 6(4), 991-999 (2014)
Articles
Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.
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