Daun02Cell viability inhibitor,DNA synthisis inhibitor CAS# 290304-24-4 |
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Quality Control & MSDS
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Chemical structure
3D structure
| Cas No. | 290304-24-4 | SDF | Download SDF |
| PubChem ID | 74891316 | Appearance | Powder |
| Formula | C41H44N2O20 | M.Wt | 884.79 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO : ≥ 100 mg/mL (113.02 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | [3-nitro-4-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl N-[(2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-3-hydroxy-2-methyloxan-4-yl]carbamate | ||
| SMILES | CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)C)O)NC(=O)OCC6=CC(=C(C=C6)OC7C(C(C(C(O7)CO)O)O)O)[N+](=O)[O-])O | ||
| Standard InChIKey | BOIXMGNMIWJAEW-LCTCPDETSA-N | ||
| Standard InChI | InChI=1S/C41H44N2O20/c1-15-31(46)20(42-40(54)59-14-17-7-8-22(21(9-17)43(56)57)62-39-38(53)37(52)34(49)25(13-44)63-39)10-26(60-15)61-24-12-41(55,16(2)45)11-19-28(24)36(51)30-29(33(19)48)32(47)18-5-4-6-23(58-3)27(18)35(30)50/h4-9,15,20,24-26,31,34,37-39,44,46,48-49,51-53,55H,10-14H2,1-3H3,(H,42,54)/t15-,20-,24-,25+,26-,31+,34-,37-,38+,39+,41-/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 | Daun02 is an inhibitor of cell viability with IC50 values of 1.5 μM, 3.5 μM and 0.5 μM, respectively in Panc02, MCF-7 and T47-D cell lines. | |||||
| Targets | Panc02 | MCF-7 | T47-D | |||
| IC50 | 1.5 μM | 3.5 μM | 0.5 μM | |||
| Cell experiment: [1] | |
| Cell lines | Panc02, MCF-7, T47-D, PC3, DU145 and LNCap cells (transduced to express E.coli β-gal) |
| Preparation method | The solubility of this compound in DMSO is >10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while.Stock solution can be stored below -20°C for several months. |
| Reacting condition | EC50: 0.5 to 5.5 μM, 24 hours |
| Applications | The prodrug Daun02 was converted to daunomycin by the β-galactosidase. It inhibited the cell viability with EC50 values of 1.5, 3.5, 0.5, 5.0, 5.5, 5.0 for Panc02, MCF-7, T47-D, PC3, DU145 and LNCap tumor cells, respectively. |
| Animal experiment: [1] | |
| Animal models | Male athymic BALB/c mice implanted with β-gal-transduced Panc02 cells |
| Dosage form | Intraperitoneal injection, 200 mg/kg |
| Application | None of the tumors responded to treatment with intraperitoneal Daun02. The dose for Daun02 was the highest tested due to the limited water solubilityof the compound. At this dose, the animals did not appear to experience anytoxicityas evidenced bynormal physical and behavioral characteristics and continued weight gain. It may be due to the less distribution and the poor penetrability of Daun02 across cell membranes. |
| Other notes | Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
| References: [1] David Farquhar, Bih Fang Pan, Mamoru Sakurai, AjitGhosh, Craig A. Mullen, J. Arly Nelson. Suicide gene therapy using E.Coli β-galactosidase. Cancer ChemotherPharmacol.2002, 50: 65–70. | |
Daun02 Dilution Calculator
Daun02 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.1302 mL | 5.6511 mL | 11.3021 mL | 22.6042 mL | 28.2553 mL |
| 5 mM | 0.226 mL | 1.1302 mL | 2.2604 mL | 4.5208 mL | 5.6511 mL |
| 10 mM | 0.113 mL | 0.5651 mL | 1.1302 mL | 2.2604 mL | 2.8255 mL |
| 50 mM | 0.0226 mL | 0.113 mL | 0.226 mL | 0.4521 mL | 0.5651 mL |
| 100 mM | 0.0113 mL | 0.0565 mL | 0.113 mL | 0.226 mL | 0.2826 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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Daun02 is an inhibitor of cell viability with IC50 values of 1.5μM, 3.5μM and 0.5μM, respectively in Panc02, MCF-7 and T47-D cell lines [1].
Daun02, an anthracycline derivative, is a substrate of β-galactosidase. β-galactosidase catalyses Daun02 into daunomycin, which causes apoptotic cell death and blockade of voltagedependent calcium channels. Daun02 has been used in the study of suicide gene therapy which has thepotential to increase the selective toxicityof conventional antitumor agents. In this study, Daun02 is shown to suppress the viability of several β-gal gene transduced tumor celllinesin vitro. However, none of thetumors responded to treatment withDaun02in vivo. This mayhave been due tothe limited aqueous solubilityof the agent.Daun02 is also used to study activated neuronal ensembles in models of conditioned drug effects and relapse. The method is called Daun02 inactivation method. In the Fos–lacZ transgenic rats, the previously drug activated neurons can be inactivated through injection of the prodrug Daun02 [1,2].
References:
[1] David Farquhar, Bih Fang Pan, Mamoru Sakurai, AjitGhosh, Craig A. Mullen, J. Arly Nelson. Suicide gene therapy using E.Coliβ-galactosidase. Cancer ChemotherPharmacol.2002, 50: 65–70.
[2] Fabio C. Cruz, EisukeKoya, Danielle H. Guez-Barber, Jennifer M. Bossert,
Carl R. Lupica, YavinShaham and Bruce T. Hope.New technologies for examining the role of neuronal ensembles in drug addiction and fear.Nature Reviews/Neuroscience. 2013, 14: 743-754.
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Daun02 Inactivation of Behaviorally Activated Fos-Expressing Neuronal Ensembles.[Pubmed:27367964]
Curr Protoc Neurosci. 2016 Jul 1;76:8.36.1-8.36.17.
Learned associations about salient experiences (e.g., drug exposure, stress) and their associated environmental stimuli are mediated by a minority of sparsely distributed, behaviorally activated neurons coined 'neuronal ensembles.' For many years, it was not known whether these neuronal ensembles played causal roles in mediating learned behaviors. However, in the last several years the 'Daun02 inactivation technique' in Fos-lacZ transgenic rats has proved very useful in establishing causal links between neuronal ensembles that express the activity-regulated protein Fos and learned behaviors. Fos-expressing neurons in these rats also express the bacterial protein beta-galactosidase (beta-gal) in strongly activated neurons. When the prodrug Daun02 is injected into the brains of these rats 90 min after a behavior (e.g., drug-seeking) or cue exposure, then Daun02 is converted into daunorubicin by beta-gal, which selectively inactivates Fos- and beta-gal-expressing neurons that were activated 90 min before the Daun02 injection. This unit presents protocols for breeding the Fos-lacZ rats and conducting appropriate Daun02 inactivation experiments. (c) 2016 by John Wiley & Sons, Inc.
