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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:
144875-48-9
Molecular Weight:
314.38
UNSPSC Code:
51111800
PubChem Substance ID:
329825221
NACRES:
NA.77
MDL number:
MFCD00937759
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
desiccated, protect from light
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Product Name

Resiquimod, ≥98% (HPLC)

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 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.
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 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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Certificates of Analysis (COA)

Lot/Batch Number
126M4718V
036M4705V
035M47102V
034M4714V
122M4728V

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Articles

Bioactive Molecules for Immunology Research

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

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
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
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Global Trade Item Number

SKUGTIN
SML0196-10MG04061837077050
SML0196-50MG04061837077067