Salinosporamide A [437742-34-2]
AG-CN2-0444
Overview
- SupplierAdipoGen Life Sciences
- Product NameSalinosporamide A [437742-34-2]
- Delivery Days Customer10
- CAS Number437742-34-2
- CertificationResearch Use Only
- Estimated Purity>95%
- Hazard InformationWarning
- Molecular FormulaC15H20ClNO4
- Molecular Weight313.8
- Scientific DescriptionChemical. CAS: 437742-34-2. Formula: C15H20ClNO4. MW: 313.8. Isolated from Salinospora tropica. Potent, irreversible inhibitor of all the 3 proteolytic activities of the mammalian 20S proteasome. beta5 subunit: chymotrypsin-like (EC50 = 3.5nM) beta2 subunit: trypsin-like (EC50 = 28nM) beta1 subunit: caspase-like or peptidyl-glutamyl peptide-hydrolyzing (PGPH) (EC50 = 430nM) Potent anticancer compound. Triggers apoptosis, with distinct proteasome activity and mechanism of action compared to bortezomib (Velcade) (Prod. No. AG-CR1-3602). Most potent suppressor of NF-kappaB activation, compared with bortezomib, MG-132 (Prod. No. AG-CP3-0011), N-acetyl-leucyl-leucyl-norleucinal (ALLN) and lactacystin (Prod. No. AG-CN2-0104). Inhibitor of TNF-alpha, IL-1, IL-6, ICAM-1 and VEGF synthesis. Displays a longer inhibition duration than bortezomib. Potent antileukemic activity against bortezomib-resistant leukemia cells. - Potent, irreversible inhibitor of all the 3 proteolytic activities of the mammalian 20S proteasome. beta5 subunit: chymotrypsin-like (EC50 = 3.5nM) beta2 subunit: trypsin-like (EC50 = 28nM) beta1 subunit: caspase-like or peptidyl-glutamyl peptide-hydrolyzing (PGPH) (EC50 = 430nM) Potent anticancer compound. Triggers apoptosis, with distinct proteasome activity and mechanism of action compared to bortezomib (Velcade) (Prod. No. AG-CR1-3602). Most potent suppressor of NF-kappaB activation, compared with bortezomib, MG-132 (Prod. No. AG-CP3-0011), N-acetyl-leucyl-leucyl-norleucinal (ALLN) and lactacystin (Prod. No. AG-CN2-0104). Inhibitor of TNF-alpha, IL-1, IL-6, ICAM-1 and VEGF synthesis. Displays a longer inhibition duration than bortezomib. Potent antileukemic activity against bortezomib-resistant leukemia cells.
- SMILES[H][C@](O)([C@@]1([H])CCCC=C1)[C@@]12NC(=O)[C@H](CCCl)[C@]1(C)OC2=O
- Storage Instruction-20°C,2°C to 8°C
- UNSPSC12352200
References
- Salinosporamide A: a highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus salinospora: R.H. Feling, et al.; Angew. Chem. Int. Ed. Engl. 42, 355 (2003)
- Structure-activity relationship studies of salinosporamide A (NPI-0052), a novel marine derived proteasome inhibitor: V.R. Macherla, et al.; J. Med. Chem. 48, 3684 (2005)
- A novel orally active proteasome inhibitor induces apoptosis in multiple myeloma cells with mechanisms distinct from Bortezomib: D. Chauhan, et al.; Cancer Cell 8, 407 (2005)
- Crystal structures of Salinosporamide A (NPI-0052) and B (NPI-0047) in complex with the 20S proteasome reveal important consequences of beta-lactone ring opening and a mechanism for irreversible binding: M. Groll, et al.; JACS 128, 5136 (2006)
- NPI-0052 enhances tumoricidal response to conventional cancer therapy in a colon cancer model: J.C. Cusack, et al.; Clin. Cancer Res. 12, 6758 (2006)
- Comparison of biochemical and biological effects of ML858 (salinosporamide A) and bortezomib: M.J. Williamson, et al.; Mol. Cancer Ther. 5, 3052 (2006)
- Salinosporamide A (NPI-0052) potentiates apoptosis, suppresses osteoclastogenesis, and inhibits invasion through down-modulation of NF-kappaB-regulated gene products: K.S. Ahn, et al.; Blood 110, 2286 (2007)
- A mechanistic and kinetic study of the beta-lactone hydrolysis of Salinosporamide A (NPI-0052), a novel proteasome inhibitor: N. Denora, et al.; J. Pharm. Sci. 96, 2037 (2007)
- Combination of proteasome inhibitors bortezomib and NPI-0052 trigger in vivo synergistic cytotoxicity in multiple myeloma: D. Chauhan, et al.; Blood 111, 1654 (2008)
- Discovery and development of the anticancer agent salinosporamide A (NPI-0052): W. Fenical, et al.; Bioorg. Med. Chem. 17, 2175 (2009)