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Acronycine

CAS# 7008-42-6

Acronycine

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Chemical structure

Acronycine

3D structure

Chemical Properties of Acronycine

Cas No. 7008-42-6 SDF Download SDF
PubChem ID 345512 Appearance Powder
Formula C20H19NO3 M.Wt 321.4
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 6-methoxy-3,3,12-trimethylpyrano[2,3-c]acridin-7-one
SMILES CC1(C=CC2=C3C(=C(C=C2O1)OC)C(=O)C4=CC=CC=C4N3C)C
Standard InChIKey SMPZPKRDRQOOHT-UHFFFAOYSA-N
Standard InChI InChI=1S/C20H19NO3/c1-20(2)10-9-13-15(24-20)11-16(23-4)17-18(13)21(3)14-8-6-5-7-12(14)19(17)22/h5-11H,1-4H3
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.
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.
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.

Acronycine Dilution Calculator

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Acronycine Molarity Calculator

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Preparing Stock Solutions of Acronycine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1114 mL 15.5569 mL 31.1139 mL 62.2278 mL 77.7847 mL
5 mM 0.6223 mL 3.1114 mL 6.2228 mL 12.4456 mL 15.5569 mL
10 mM 0.3111 mL 1.5557 mL 3.1114 mL 6.2228 mL 7.7785 mL
50 mM 0.0622 mL 0.3111 mL 0.6223 mL 1.2446 mL 1.5557 mL
100 mM 0.0311 mL 0.1556 mL 0.3111 mL 0.6223 mL 0.7778 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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References on Acronycine

Acronycine derivatives: a promising series of anticancer agents.[Pubmed:19594412]

Anticancer Agents Med Chem. 2009 Sep;9(7):804-15. Epub 2009 Sep 1.

The pyranoacridone Acronycine (1) exhibits antitumor properties against a large panel of solid tumor models, but its moderate potency and low water solubility severely hampered the subsequent clinical trials. Development of synthetic analogues followed the isolation from several Sarcomelicope species of Acronycine epoxide (17), which led to a hypothesis of bioactivation of Acronycine by transformation of the 1,2-double bond into the corresponding oxirane. 1,2-Diacyloxy-1,2-dihydroAcronycine derivatives exhibited antitumor properties, with a broadened spectrum of activity and an increased potency. The demonstration that Acronycine interacted with DNA led to the development of benzo[a], [b], and [c]Acronycine analogs. 1,2-Dihydroxy-1,2-dihydrobenzo[b]Acronycine esters and diesters were active in human orthotopic models of cancers xenografted in nude mice. The activity of these compounds, exemplified by cis-1,2-diacetoxy-1,2-dihydrobenzo[b]Acronycine (49), developed in phase I clinical trials under the code S23906-1, was correlated with their ability to give covalent adducts with DNA, involving reaction between the N-2 amino group of guanines in the minor groove and the ester group at the benzylic position of the drug. The influence of the kinetics of DNA alkylation on the cytotoxic and antitumor properties showed a strong correlation between antiproliferative activity and DNA alkylation kinetics, with the most cytotoxic compounds, appearing as the slowest DNA alkylators. Hybrid compounds associating the acridone or benzo[b]acridone chromophore of Acronycine derivatives and the epoxyfuran alkylating unit present in psorospermin also displayed potent antiproliferative activities, alkylating DNA guanine units at position N-7 in the major groove, as natural xanthones belonging to the psorospermin series.

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