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SML0196

Sigma-Aldrich

Resiquimod

≥98% (HPLC)

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:
12352200
PubChem Substance ID:
329825221
NACRES:
NA.77

Quality Level

100

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

11 - Combustible Solids

wgk_germany

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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Sylvia Adams
Immunotherapy, 1(6), 949-964 (2010-06-22)
Toll-like receptors (TLRs) are pattern-recognition receptors related to the Drosophila Toll protein. TLR activation alerts the immune system to microbial products and initiates innate and adaptive immune responses. The naturally powerful immunostimulatory property of TLR agonists can be exploited for
Angeline Rouers et al.
EBioMedicine, 21, 158-169 (2017-06-16)
HIV-specific broadly neutralizing antibodies (bnAbs) have been isolated from patients with high viremia but also from HIV controllers that repress HIV-1 replication. In these elite controllers (ECs), multiple parameters contribute to viral suppression, including genetic factors and immune responses. Defining
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
Gonca E Karahan et al.
Transplantation, 103(4), 716-723 (2018-11-13)
Pretransplant immunological risk assessment is currently based on donor-specific HLA antibodies in serum. Despite being an excellent source for antibodies produced by bone marrow-residing plasma cells, serum analysis does not provide information on the memory B-cell compartment. Although B-cell culture
The inhibition of malignant melanoma cell invasion of bone by the TLR7 agonist R848 is dependent upon pro-inflammatory cytokines produced by bone marrow macrophages
Manome Y, et al.
Oncotarget, 9(52), 29934-29934 (2018)
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