NSC 144303 (also known as Ubiquitin Isopeptidase Inhibitor I, G5) is a novel and potent apoptosome-independent caspase and apoptosis activator with IC50 values of 1.76 and 1.6 μM in E1A and E1A/C9DN cells, respectively. Additionally, it is a strong inhibitor of DUB activity in general, which causes acute proteotoxic stress and apoptosis and causes apoptosis in Bcl-2 over-expressing cells.
Physicochemical Properties
| Molecular Formula | C19H14N2O7S |
| Molecular Weight | 414.388663768768 |
| Exact Mass | 414.052 |
| Elemental Analysis | C, 55.07; H, 3.41; N, 6.76; O, 27.03; S, 7.74 |
| CAS # | 108477-18-5 |
| Related CAS # | 108477-18-5 |
| PubChem CID | 5918438 |
| Appearance | Solid powder |
| LogP | 5.094 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 29 |
| Complexity | 767 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | S1(C/C(=C\C2C=CC(=CC=2)[N+](=O)[O-])/C(/C(=C/C2C=CC(=CC=2)[N+](=O)[O-])/C1)=O)(=O)=O |
| InChi Key | SSAMIOWVUGBIJK-KAVGSWPWSA-N |
| InChi Code | InChI=1S/C19H14N2O7S/c22-19-15(9-13-1-5-17(6-2-13)20(23)24)11-29(27,28)12-16(19)10-14-3-7-18(8-4-14)21(25)26/h1-10H,11-12H2/b15-9+,16-10+ |
| Chemical Name | (3Z,5Z)-3,5-bis[(4-nitrophenyl)methylidene]-1,1-dioxothian-4-one |
| Synonyms | Ubiquitin Isopeptidase Inhibitor I; NSC-144303; NSC144303; NSC 144303; G5 |
| 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: This product is not stable in solution, please use freshly prepared working solution for optimal results. |
| 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 | E1A cells (IC50 = 1.76 μM); E1A/C9DN cells (IC50 = 1.6 μM) |
| ln Vitro | By blocking ubiquitin peptidase, it suppresses the ubiquitin kinase body system. Kinase-independent pathways can be activated by G5. G5 has the ability to trigger several unusual kinase pathways, such as the apoptotic body's Bcl-2-dependent mitochondrial pathway. It can also increase the stability of the BH3 protein Noxa, the antagonist Smac, and the death receptor pathway. With IC50s of 1.76 and 1.6 μM in E1A and E1A/C9DN cells, respectively, G5 is a powerful inducer of cell death [1]. |
| References | [1]. Aleo E, et al. Identification of new compounds that trigger apoptosome-independent caspase activation and apoptosis. Cancer Res. 2006 Sep 15;66(18):9235-44 |
Solubility Data
| Solubility (In Vitro) |
DMSO: ~50 mg/mL (~120.7 mM; Need ultrasonic) THF: ~3.4 mg/mL (~8.3 mM; Need ultrasonic) Acetone: ~2.9 mg/mL (~6.9 mM; Need ultrasonic) Ethanol: < 1 mg/mL (ultrasonic) (insoluble) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 10 mg/mL (24.13 mM) in 15% Cremophor EL 85% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O 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 | 2.4132 mL | 12.0659 mL | 24.1319 mL | |
| 5 mM | 0.4826 mL | 2.4132 mL | 4.8264 mL | |
| 10 mM | 0.2413 mL | 1.2066 mL | 2.4132 mL |