CAS 144875-48-9|Resiquimod
Introduction：Basic information about CAS 144875-48-9|Resiquimod, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Resiquimod | ||
|---|---|---|---|
| CAS Number | 144875-48-9 | Molecular Weight | 314.382 |
| Density | 1.3±0.1 g/cm3 | Boiling Point | 553.6±50.0 °C at 760 mmHg |
| Molecular Formula | C17H22N4O2 | Melting Point | 193 °C |
| MSDS | ChineseUSA | Flash Point | 288.6±30.1 °C |
Names
| Name | resiquimod |
|---|---|
| Synonym | More Synonyms |
Resiquimod BiologicalActivity
| Description | Resiquimod is a Toll-like receptor 7 and 8 (TLR7/TLR8) agonist that induces the upregulation of cytokines such as TNF-α, IL-6 and IFN-α. |
|---|---|
| Related Catalog | Signaling Pathways >>Immunology/Inflammation >>Toll-like Receptor (TLR)Research Areas >>Inflammation/Immunology |
| In Vitro | Resiquimod (R-848) induces both hapten- and allergen-specific circulating T cells, including TH2 effectors, to produce IFN-γ and even to lose the ability to produce IL-4[2]. Resiquimod (R848) enhances PBL proliferation in a dose-dependent manner, and increases the number of BrdU-positive cells in BrdU incorporation assay. Cells treated with R848 exhibits significantly increased (3.5-fold) luciferase (a reporter of NF-κB activity) activity[3]. |
| In Vivo | Resiquimod (R-848) (50 μg/bird, i.m. route) significantly up-regulates the expression of IFN-α, IFN-β, IFN-γ, IL-1β, IL-4, iNOS and MHC-II genes in SPF chicken[1]. |
| Kinase Assay | For luciferase assay, FG-9307 cells are transfected with the firefly NF-κB-specific luciferase reporter vector pNFκB-Met-Luc2. Transfection efficiency is monitored by co-transfection with the pSEAP2 control vector, which constitutively expresses the human secreted enhanced alkaline phosphatase (SEAP). Then the cells are treated with Resiquimod (R848, 1 µg/mL), CQ (10 µM), CQ plus R848 or PBS and incubated at 22°C for 24 h. The culture medium of the transfectants is then analyzed for luciferase activity and SEAP activity using Luciferase Assay Kit and the Great EscAPe™ SEAP Chemiluminescence Detection Kit, respectively. The assay is performed three times. |
| Cell Assay | For inhibition of lysosomal acidification, cells are incubated with 10 µM CQ for 1 h before Resiquimod (R848) treatment. After treatment, 20 µL of 5 mg/mL MTT is added to the plate. The plate is incubated at 22°C for 4 h, and 200 µL dimethyl sulfoxide is added to the plate to dissolve the reduced formazan. The plate is then read at 490 nm with a microplate reader. To determine the effect of Myd88 inhibition on R848-induced cell proliferation, the Myd88 inhibitor Pepinh-MYD and the control peptide Pepinh-Control are added to PBL at the concentration of 50 µM, and the plate is incubated at 22°C for 6 h. After incubation, the cells are treated with R848 and subjected to MTT assay as above. To determine the effect of NF-κB inactivation on R848-induced cell proliferation, BAY-11-7082, an irreversible inhibitor of IκB-α phosphorylation, is added to the cells at the concentration of 1 µM, and the plate is incubated at 22°C for 1 h. After incubation, the cells are treated with R848 and subjected to MTT assay as earlier. All experiments are performed three times. |
| Animal Admin | A total of 40 SPF chickens of two-week old are allotted to one of the following four experimental groups (n=10/group): Group A: PBS control; Group B: inactivated NDV vaccine; Group C: commercial oil adjuvanted inactivated NDV vaccine prepared from lentogenic strain and Group D: combination of inactivated NDV vaccine and R-848 (50 μg/bird). Vaccine or PBS is administered by intramuscular route in the thigh muscle. A booster dose is given 14-day post immunization (d.p.i). Two weeks post-booster, experimental SPF birds are challenged with velogenic strain of NDV (105 ELD50 per bird) intramuscularly. Clinical signs and mortality are observed daily till 14 day post-challenge (d.p.c). Cloacal swabs (n=6/group) are collected from the birds on day 0, 4, 7 and 14 post-challenge and inoculated into 10-day old embryonated chicken eggs (n=3 eggs/sample) through intra-allantoic route. Three day post-inoculation, the allantoic fluid is checked for the NDV growth by spot haemagglutination using 10% chicken RBC. |
| References | [1]. Sachan S, et al. Adjuvant potential of resiquimod with inactivated Newcastle disease vaccine and its mechanism of action in chicken. Vaccine. 2015 Aug 26;33(36):4526-32. [2]. Brugnolo F, et al. The novel synthetic immune response modifier R-848 (Resiquimod) shifts human allergen-specific CD4+ TH2 lymphocytes into IFN-gamma-producing cells. J Allergy Clin Immunol. 2003 Feb;111(2):380-8. [3]. Zhou ZX, et al. Immune effects of R848: evidences that suggest an essential role of TLR7/8-induced, Myd88- and NF-κB-dependent signaling in the antiviral immunity of Japanese flounder (Paralichthys olivaceus). Dev Comp Immunol. 2015 Mar;49(1):113-20. |
Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
|---|---|
| Boiling Point | 553.6±50.0 °C at 760 mmHg |
| Melting Point | 193 °C |
| Molecular Formula | C17H22N4O2 |
| Molecular Weight | 314.382 |
| Flash Point | 288.6±30.1 °C |
| Exact Mass | 314.174286 |
| PSA | 86.19000 |
| LogP | 2.15 |
| Vapour Pressure | 0.0±1.6 mmHg at 25°C |
| Index of Refraction | 1.635 |
| InChIKey | BXNMTOQRYBFHNZ-UHFFFAOYSA-N |
| SMILES | CCOCc1nc2c(N)nc3ccccc3c2n1CC(C)(C)O |
Safety Information
| RIDADR | NONH for all modes of transport |
|---|---|
| RTECS | NJ5911320 |
| HS Code | 2933990090 |
Customs
| HS Code | 2933990090 |
|---|---|
| Summary | 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
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Synonyms
| 1-[4-Amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methyl-2-propanol |
| 1H-imidazo[4,5-c]quinoline-1-ethanol, 4-amino-2-(ethoxymethyl)-α,α-dimethyl- |
| Resiquimod |
| 1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol |
| 1-(4-Amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol |
| 4-amino-2-(ethoxymethyl)-a,a-dimethyl-1h-imidazo[4,5-c]quinoline-1-ethanol |
| 1-[4-Amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol |
| R848 |
