CAS 886578-07-0|6,6',7,7'-TETRAHYDROXY-5,5'-DIISOPROPYL-3,3'-DIMETHYL-[2,2'-BINA
Introduction：Basic information about CAS 886578-07-0|6,6',7,7'-TETRAHYDROXY-5,5'-DIISOPROPYL-3,3'-DIMETHYL-[2,2'-BINA, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | 6,6',7,7'-TETRAHYDROXY-5,5'-DIISOPROPYL-3,3'-DIMETHYL-[2,2'-BINAPHTHALENE]-1,1',4,4'-TETRAONE | ||
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| CAS Number | 886578-07-0 | Molecular Weight | 490.50 |
| Density | / | Boiling Point | / |
| Molecular Formula | C28H26O8 | Melting Point | / |
| MSDS | / | Flash Point | / |
Names
| Name | 6-(1,4-dihydroxy-3-methyl-6,7-dioxo-5-propan-2-ylnaphthalen-2-yl)-5,8-dihydroxy-7-methyl-1-propan-2-ylnaphthalene-2,3-dione |
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| Synonym | More Synonyms |
BiologicalActivity
| Description | Apogossypolone (ApoG2) is an orally active Bcl-2 family proteins inhibitor with Ki values of 35, 25 and 660 nM for Bcl-2, Mcl-1 and Bcl-XL, respectively. Apogossypolone shows antitumor activities, induces cell apoptosis[1] and autophagy[2]. Apogossypolone also has antifungal activity[3]. |
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| Related Catalog | Signaling Pathways >>Apoptosis >>Bcl-2 FamilySignaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerResearch Areas >>InfectionSignaling Pathways >>Anti-infection >>FungalSignaling Pathways >>Protein Tyrosine Kinase/RTK >>ROSSignaling Pathways >>Autophagy >>Autophagy |
| Target | Mcl-1:25 nM (Ki) Bcl-2:35 nM (Ki) Bcl-xL:660 nM (Ki) |
| In Vitro | Apogossypolone (ApoG2) shows improved stability under stressed conditions[1]. Apogossypolone (0-1 µM, 72 or 96 h) inhibits WSU-DLCL2 cells growth in a dose-dependent manner[1]. Apogossypolone (0-5 µM, 24 or 48 h) interferes with the formation of heterodimers between anti-apoptotic and pro-apoptotic Bcl-2 family members, and leads to cleavage of caspase-3, caspase-9 and PARP[1]. Apogossypolone (0-8 µM, 0-72 h) induces apoptotic WSU-DLCL2 cell death in a time- and dose-dependent manner[1]. Apogossypolone (0-10 µM, 0-24 h) induces autophagy and promotes ROS generation in HCC cells[2]. Cell Proliferation Assay[1] Cell Line: WSU-DLCL2 Concentration: 250, 350, 500 and 1000 nM Incubation Time: 96 h for cell counting, 72 h for MTT Result: Inhibited growth in a dose-dependent manner. The 50% growth inhibition concentration (IC50) was approximately 350 nM. Western Blot Analysis[1] Cell Line: WSU-DLCL2 Concentration: 0.35, 0.5, 1 and 5 µM Incubation Time: 24 or 48 h Result: Blocked the formation of heterodimers between Bcl-XL and Bim in a concentration-dependent manner. Resulted in the activation of cleavages of caspase-3, caspase-9 and PARP. Apoptosis Analysis[1] Cell Line: WSU-DLCL2 Concentration: 0, 1, 2, 4 and 8 µM Incubation Time: 24, 48 and 72 h Result: Induced cell apoptosis in a time- and dose-dependent manner. Cell Autophagy Assay[2] Cell Line: HepG2 and Hep3B Concentration: 1.25, 2.5, 5 and 10 µM Incubation Time: 6, 12, 18 and 24 h Result: Induced LC3 (Light chain 3)-II conversion in a dose- and time-dependent manner. |
| In Vivo | Apogossypolone (ApoG2) (120 mg/kg; i.v. or p.o.; once a day for 5 days) effectively inhibits growth of diffuse large cell lymphoma cells without toxicity[1]. Animal Model: Four-week-old female ICR-SCID mice, each mouse received 107 WSU-DLCL2 cells (in serum-free RPMI 1640) subcutaneously (sc) in each flank area[1] Dosage: 120 mg/kg Administration: Intravenous or administration per day for five days Result: Inhibited the growth of WSU-DLCL2 and significantly decreased the tumor weight. Animal Model: Non-tumor-bearing SCID mice[1] Dosage: 160 mg/kg Administration: Intravenous or administration per day for five days Result: Was well tolerated in mice up to 800 mg/kg. Displayed no gross signs of toxicity. |
| References | [1]. Yuan Sun, et al. Apogossypolone, a nonpeptidic small molecule inhibitor targeting Bcl-2 family proteins, effectively inhibits growth of diffuse large cell lymphoma cells in vitro and in vivo. Cancer Biol Ther. 2008 Sep;7(9):1418-26. [2]. Cheng P, et al. The novel BH-3 mimetic apogossypolone induces Beclin-1- and ROS-mediated autophagy in human hepatocellular carcinoma [corrected] cells. Cell Death Dis. 2013 Feb 7;4(2):e489. [3]. Jay E Mellon, et al. Inhibitory effects of gossypol, gossypolone, and apogossypolone on a collection of economically important filamentous fungi. J Agric Food Chem. 2012 Mar 14;60(10):2740-5. |
Chemical & Physical Properties
| Molecular Formula | C28H26O8 |
|---|---|
| Molecular Weight | 490.50 |
| Exact Mass | 490.16300 |
| PSA | 149.20000 |
| LogP | 4.84700 |
| InChIKey | PXSGRWNXASCGTJ-UHFFFAOYSA-N |
| SMILES | Cc1c(-c2c(C)c(=O)c3c(C(C)C)c(=O)c(=O)cc-3c2=O)c(O)c2cc(O)c(O)c(C(C)C)c2c1O |
| Storage condition | -20℃ |
Synonyms
| apogossypolone |
| 6,6',7,7'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-2,2'-binaphthyl-1,1',4,4'-tetraone |
