LCL521 dihydrochloride (1,3DMG-B13 dihydrochloride) is a novel and potent acid ceramidase (ACDase) inhibitor. LCL521 also inhibits the lysosomal acid sphingomyelinase (ASMase).
Physicochemical Properties
| Molecular Formula | C31H54CL2N4O7 |
| Molecular Weight | 665.689067363739 |
| Exact Mass | 664.336 |
| CAS # | 1226759-47-2 |
| Related CAS # | LCL521;1226851-11-1 |
| PubChem CID | 132585217 |
| Appearance | Off-white to light yellow solid powder |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 24 |
| Heavy Atom Count | 44 |
| Complexity | 780 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | Cl.Cl.O(C(CN(C)C)=O)[C@H](C1C=CC(=CC=1)[N+](=O)[O-])[C@@H](COC(CN(C)C)=O)NC(CCCCCCCCCCCCC)=O |
| InChi Key | RGUSRMLMLNVDSF-QJCVVZHISA-N |
| InChi Code | InChI=1S/C31H52N4O7.2ClH/c1-6-7-8-9-10-11-12-13-14-15-16-17-28(36)32-27(24-41-29(37)22-33(2)3)31(42-30(38)23-34(4)5)25-18-20-26(21-19-25)35(39)40/h18-21,27,31H,6-17,22-24H2,1-5H3,(H,32,36)2*1H/t27-,31-/m1../s1 |
| Chemical Name | (1R,2R)-1-(4-nitrophenyl)-2-tetradecanamidopropane-1,3-diyl bis(2-(dimethylamino)acetate) dihydrochloride |
| Synonyms | LCL521 dihydrochloride LCL-521 dihydrochloride LCL 521 dihydrochloride |
| 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 | LCL521 (1 µM) is a powerful inhibitor of cellular ACDase activity, but 10 µM LCL521 has an extra, weakened action on the alpha form of this enzyme. LCL521 (10μM) causes a time-dependent (1 hour and 5 hour) decrease of α-ACDase forms in MCF7 cells [1]. |
| References |
[1]. Targeting (cellular) lysosomal acid ceramidase by B13: design, synthesis and evaluation of novel DMG-B13 ester prodrugs. Bioorg Med Chem. 2014 Dec 15;22(24):6933-44. |
Solubility Data
| Solubility (In Vitro) |
H2O : ~100 mg/mL (~150.22 mM) DMSO : ~20.83 mg/mL (~31.29 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.12 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 (3.12 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 (3.12 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. Solubility in Formulation 4: 50 mg/mL (75.11 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.5022 mL | 7.5110 mL | 15.0220 mL | |
| 5 mM | 0.3004 mL | 1.5022 mL | 3.0044 mL | |
| 10 mM | 0.1502 mL | 0.7511 mL | 1.5022 mL |