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Merck

SML0196

Sigma-Aldrich

Resiquimod

≥98% (HPLC), powder, TLR7/TLR8 agonist

Sinónimos:

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

Fórmula empírica (notación de Hill):
C17H22N4O2
Número de CAS:
Peso molecular:
314.38
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Visite la Librería de documentos

Anette Christ et al.
Cell, 172(1-2), 162-175 (2018-01-13)
Long-term epigenetic reprogramming of innate immune cells in response to microbes, also termed "trained immunity," causes prolonged altered cellular functionality to protect from secondary infections. Here, we investigated whether sterile triggers of inflammation induce trained immunity and thereby influence innate
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)
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)
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
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)

Artículos

Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.

Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.

Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.

Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.

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