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SML0196

Sigma-Aldrich

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:
144875-48-9
Molecular Weight:
314.38
MDL number:
MFCD00937759
UNSPSC Code:
51111800
PubChem Substance ID:
329825221
NACRES:
NA.77

product name

Resiquimod, ≥98% (HPLC)

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

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

Application

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.
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.
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. It is a recommended topical drug for treating skin tumors like actinic keratosis (AK) and superficial basal cell carcinoma.

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
Matthew S Block et al.
Melanoma research, 29(4), 420-427 (2018-12-07)
A vaccine that could expand melanoma-specific T cells might reduce the risk of recurrence of resected melanoma and could provide an alternative or adjunct to standard immunotherapy options. We tested the safety and immunogenicity of a vaccine coupling a melanoma-associated
Paeonol ameliorates imiquimod-induced psoriasis-like skin lesions in BALB/c mice by inhibiting the maturation and activation of dendritic cells
Meng Y, et al.
International Journal of Molecular Medicine, 39(5), 1101-1110 (2017)
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