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SML0196

Sigma-Aldrich

Resiquimod

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

Synonyme(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

Formule empirique (notation de Hill):
C17H22N4O2
Numéro CAS:
144875-48-9
Poids moléculaire :
314.38
Numéro MDL:
MFCD00937759
Code UNSPSC :
51111800
ID de substance PubChem :
329825221
Nomenclature NACRES :
NA.77

product name

Resiquimod, ≥98% (HPLC)

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated
protect from light

Couleur

white to tan

Solubilité

DMSO: 10 mg/mL, clear (warmed to 60 °C)

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

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)

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

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)
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)
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)
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
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