Demethoxyfumitremorgin CCAS# 111768-16-2 |
- Demethoxy-3-epifumitremorgin C
Catalog No.:BCC8315
CAS No.:106292-68-6
Quality Control & MSDS
3D structure
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| Cas No. | 111768-16-2 | SDF | Download SDF |
| PubChem ID | 10337896 | Appearance | Powder |
| Formula | C21H23N3O2 | M.Wt | 349.43 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| SMILES | CC(=CC1C2=C(CC3N1C(=O)C4CCCN4C3=O)C5=CC=CC=C5N2)C | ||
| Standard InChIKey | LQXCSIKDOISJTI-BZSNNMDCSA-N | ||
| Standard InChI | InChI=1S/C21H23N3O2/c1-12(2)10-17-19-14(13-6-3-4-7-15(13)22-19)11-18-20(25)23-9-5-8-16(23)21(26)24(17)18/h3-4,6-7,10,16-18,22H,5,8-9,11H2,1-2H3/t16-,17-,18-/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 1. Demethoxyfumitremorgin C inhibits the proliferation of PC3 human prostate cancer cells via the intrinsic (mitochondrial) and extrinsic pathway, followed by downstream events leading to apoptotic cell death, it could therefore, serve as a useful agent to treat human advanced prostate cancer. 2. Demethoxyfumitremorgin C and tryprostatin B are fungal inhibitors of mammalian cell cycle progression at the G(2)/M transition. |
| Targets | PI3K | Akt | Bcl-2/Bax | Caspase | PARP | Antifection |
Demethoxyfumitremorgin C Dilution Calculator
Demethoxyfumitremorgin C Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.8618 mL | 14.309 mL | 28.618 mL | 57.2361 mL | 71.5451 mL |
| 5 mM | 0.5724 mL | 2.8618 mL | 5.7236 mL | 11.4472 mL | 14.309 mL |
| 10 mM | 0.2862 mL | 1.4309 mL | 2.8618 mL | 5.7236 mL | 7.1545 mL |
| 50 mM | 0.0572 mL | 0.2862 mL | 0.5724 mL | 1.1447 mL | 1.4309 mL |
| 100 mM | 0.0286 mL | 0.1431 mL | 0.2862 mL | 0.5724 mL | 0.7155 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Synthesis and evaluation of tryprostatin B and demethoxyfumitremorgin C analogues.[Pubmed:10780915]
J Med Chem. 2000 Apr 20;43(8):1577-85.
Tryprostatin B and Demethoxyfumitremorgin C are fungal inhibitors of mammalian cell cycle progression at the G(2)/M transition. N-Alkyl derivatives of the L-Trp-L-Pro diketopiperazine were prepared as analogues of tryprostatin B, and two of these were more active than the natural product. A second series of cis- and trans-tetrahydro-beta-carbolines annulated to a diketopiperazine were prepared as analogues of Demethoxyfumitremorgin C. The nature of the alkyl substituent, as well as its cis or trans relationship in the tetrahydro-beta-carboline ring, was found to have a significant effect on cytotoxic activity. Small cis-alkyl substituents fall into the Demethoxyfumitremorgin C family, whereas bulky benzyl trans compounds appear to act via a different mechanism of action.
Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. I. Taxonomy, fermentation, isolation and biological properties.[Pubmed:8698634]
J Antibiot (Tokyo). 1996 Jun;49(6):527-33.
Two novel diketopiperazines named tryprostatins A (1) and B (2) and a new natural product belonging to the diketopiperazine series, designated as Demethoxyfumitremorgin C (3), together with four known diketopiperazines, fumitremorgin C (4), 12,13-dihydroxyfumitremorgin C (5), fumitremorgin B (6) and verruculogen (7), were isolated from the fermentation broth of Aspergillus fumigatus BM939 by the combined use of solvent extraction, silica gel column chromatography, preparative TLC and repeated-preparative HPLC. The diketopiperazines showed an inhibitory activity on the cell cycle progression of mouse tsFT210 cells in the M phase with the MIC values of 16.4 microM (1), 4.4 microM (2), 0.45 microM (3), 4.1 microM (4), 60.8 microM (5), 26.1 microM (6) and 12.2 microM (7), respectively.
Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. II. Physico-chemical properties and structures.[Pubmed:8698635]
J Antibiot (Tokyo). 1996 Jun;49(6):534-40.
Two novel diketopiperazines named tryprostatins A and B and a new natural product belonging to the diketopiperazine series, designated as Demethoxyfumitremorgin C, together with four known diketopiperazines, fumitremorgin C, 12,13-dihydroxyfumitremorgin C, fumitremorgin B and verruculogen, are new M phase inhibitors of the mammalian cell cycle, which were isolated from the secondary metabolites of Aspergillus fumigatus. The structures of tryprostatins A, B and Demethoxyfumitremorgin C were determined mainly by the use of spectroscopic methods especially by detailed analyses of their 1H and 13C NMR spectra with the aid of 2D NMR techniques including pulse field gradient heteronuclear multiple-bond correlation (PFG-HMBC) spectroscopy. Their absolute configurations were determined on the basis of the optical rotational values and CD spectra.
Apoptotic effect of demethoxyfumitremorgin C from marine fungus Aspergillus fumigatus on PC3 human prostate cancer cells.[Pubmed:28359723]
Chem Biol Interact. 2017 May 1;269:18-24.
Demethoxyfumitremorgin C, a secondary metabolite of the marine fungus, Aspergillus fumigatus, had been reported to demonstrate cytotoxic effect on mouse tsFT210 cells. However, no information is available regarding its functional mechanism and the chemo-sensitization effects on different kinds of human cancer cells. We found that treatment of Demethoxyfumitremorgin C inhibited the cell viability of PC3 human advanced prostate cancer cells, induced apoptosis as determined by Annexin V/propidium iodide double staining, and decreased mitochondrial membrane potential. Demethoxyfumitremorgin C induced apoptosis was associated with downregulation of anti-apoptotic proteins: Ras, PI3K, Akt, Bcl-xL, and Bcl-2, and upregulation of pro-apoptotic Bax. Demethoxyfumitremorgin C activated caspase-3, -8, and -9, leading to PARP cleavage. Additionally, caspase inhibitors blocked Demethoxyfumitremorgin C-induced apoptosis of PC3 cells. These results suggest that Demethoxyfumitremorgin C from Aspergillus fumigatus inhibits the proliferation of PC3 human prostate cancer cells via the intrinsic (mitochondrial) and extrinsic pathway, followed by downstream events leading to apoptotic cell death. Demethoxyfumitremorgin C could therefore, serve as a useful agent to treat human advanced prostate cancer.
