Physicochemical Properties
| Molecular Formula | C22H27CL2N5 |
| Molecular Weight | 432.389282464981 |
| Exact Mass | 431.164 |
| CAS # | 1620278-72-9 |
| Related CAS # | TLR7/8 agonist 1;1258457-59-8 |
| PubChem CID | 90286091 |
| Appearance | Off-white to light yellow solid powder |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 29 |
| Complexity | 464 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | Cl.Cl.N1(C(CC2C=CC(CN)=CC=2)=NC2C(N)=NC3C=CC=CC=3C1=2)CCCC |
| InChi Key | YKZCFKIAMHQQAW-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C22H25N5.2ClH/c1-2-3-8-19-26-20-21(17-6-4-5-7-18(17)25-22(20)24)27(19)14-16-11-9-15(13-23)10-12-16;;/h4-7,9-12H,2-3,8,13-14,23H2,1H3,(H2,24,25);2*1H |
| Chemical Name | 1-[[4-(aminomethyl)phenyl]methyl]-2-butylimidazo[4,5-c]quinolin-4-amine;dihydrochloride |
| Synonyms | TLR7/8 agonist 5d TLR7/8 agonist5d TLR7/8 agonist-5d |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | TLR7/8 agonist 1 (compound 5d) exhibited strong immunostimulatory action. With minimal activity loss, TLR7/8 agonist 1 acts as an easy precursor for fluorophore covalent attachment. With an EC50 of 20 nM, TLR7/8 Agonist 1 maintains TLR7 agonistic activity [1]. A preliminary screen of human TLR7 (50 nM) and TLR8 (55 nM) revealed considerably differing agonistic potencies for TLR7/8 agonist 1 (Compound 1) [2]. |
| References |
[1]. Syntheses of fluorescent imidazoquinoline conjugates as probes of Toll-like receptor 7. Bioorg Med Chem Lett. 2010 Nov 15;20(22):6384-6. [2]. Structure-Based Design of Human TLR8-Specific Agonists with Augmented Potency and Adjuvanticity. J Med Chem. 2015 Oct 8;58(19):7833-49. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~83.33 mg/mL (~192.72 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.81 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (4.81 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (4.81 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3127 mL | 11.5636 mL | 23.1273 mL | |
| 5 mM | 0.4625 mL | 2.3127 mL | 4.6255 mL | |
| 10 mM | 0.2313 mL | 1.1564 mL | 2.3127 mL |