Physicochemical Properties
| Molecular Formula | C33H31N3O7 |
| Molecular Weight | 581.61514878273 |
| Exact Mass | 581.216 |
| CAS # | 2487550-41-2 |
| PubChem CID | 156599565 |
| Appearance | White to off-white solid powder |
| LogP | 2.9 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 12 |
| Heavy Atom Count | 43 |
| Complexity | 945 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | O(CC1C=CC=C(C2C=CC=CC=2)C=1C)C1=CC(=C(C=C1[N+](=O)[O-])CN[C@H](C(=O)O)C(C)O)OCC1C=CC=C(C#N)C=1 |
| InChi Key | KDEQMCUCWNLUJE-LKYSYNKGSA-N |
| InChi Code | InChI=1S/C33H31N3O7/c1-21-26(12-7-13-28(21)25-10-4-3-5-11-25)20-43-31-16-30(42-19-24-9-6-8-23(14-24)17-34)27(15-29(31)36(40)41)18-35-32(22(2)37)33(38)39/h3-16,22,32,35,37H,18-20H2,1-2H3,(H,38,39)/t22?,32-/m0/s1 |
| Chemical Name | (2S)-2-[[2-[(3-cyanophenyl)methoxy]-4-[(2-methyl-3-phenylphenyl)methoxy]-5-nitrophenyl]methylamino]-3-hydroxybutanoic acid |
| 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 |
| 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
| Targets | IC50: 2.7 nM (PD-1/PD-L1)[1]. |
| ln Vitro | Compound B2, PD-1/PD-L1-IN-10, even at low concentrations of 1 nM, significantly increases interferongamma secretion in vitro in a dose-dependent manner[1]. The viability of LLC cells and lymph node T-cells is unaffected by PD-1/PD-L1-IN-10 (compound B2)[1]. Compound B2, 0-100 nM, PD-1/PD-L1-IN-10, stabilizes the PD-L1 protein in mouse Lewis lung carcinoma (LLC) cells. Specifically, at 58 °C, compound B2, PD-1/PD-L1-IN-10, sustains the PD-L1 stability in a dose-dependent manner. suggesting that compound B2, PD-1/PD-L1-IN-10, may bind to the PD-L1 protein directly after entering LLC cells[1]. |
| ln Vivo | PD-1/PD-L1-IN-10 (compound B2, 5 mg/kg, intragastric gavage) in an LLC-bearing allograft mice model demonstrates strong in vivo anticancer activity. In LLC tumor tissues, PD-1/PD-L1-IN-10 (compound B2) efficiently inhibits tumor cell proliferation and triggers apoptosis. |
| Animal Protocol |
Animal/Disease Models: LLC tumor-bearing mice[1]. Doses: 2, 5 mg/kg. Route of Administration: ig, qd., for 21 days Experimental Results: Dramatically suppressed the growth of the tumor in a dose-dependent manner compared with the vehicle group. |
| References |
[1]. Design, Synthesis, and Evaluation of o-(Biphenyl-3-ylmethoxy)nitrophenyl Derivatives as PD-1/PD-L1 Inhibitors with Potent Anticancer Efficacy In Vivo. J Med Chem. 2021 May 26. |
Solubility Data
| Solubility (In Vitro) | DMSO : 100 mg/mL (171.93 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.30 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 25.0 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.7193 mL | 8.5967 mL | 17.1934 mL | |
| 5 mM | 0.3439 mL | 1.7193 mL | 3.4387 mL | |
| 10 mM | 0.1719 mL | 0.8597 mL | 1.7193 mL |