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Doxorubicin

Catalog No.
A3966
DNA topoisomerase II inhibitor
Grouped product items
SizePriceStock Qty
10mM (in 1mL DMSO)
$72.00
In stock
Evaluation Sample
$30.00
In stock
10mg
$66.00
In stock
25mg
$92.00
In stock
100mg
$211.00
In stock
For scientific research use only and should not be used for diagnostic or medical purposes.

Tel: +1-832-696-8203

Email: [email protected]

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Background

Doxorubicin (CAS 23214-92-8) is an anthracycline antibiotic commonly used as an anti-cancer agent targeting DNA replication machinery. Its mechanism of action involves intercalation into DNA double helices and subsequent inhibition of DNA topoisomerase II, impeding DNA synthesis and causing genomic instability. Additionally, Doxorubicin mediates chromatin remodeling by facilitating histone displacement from active chromatin, contributing further to DNA damage and transcriptional dysregulation. It is extensively employed in studies involving hematologic malignancies, solid tumors, and sarcomas, frequently serving as a chemotherapeutic reference compound. In biochemical assays, Doxorubicin has demonstrated inhibitory effects on Topoisomerase II with an IC50 typically ranging between 1-10 µM, depending on assay conditions and cell lines applied.

References:
[1]Brayfield, A, ed. (2013). Doxorubicin. Martindale: The Complete Drug Reference. Pharmaceutical Press. Retrieved 15 April 2014.
[2]Pommier Y., et al. (2010). DNA topoisomerases and their poisoning by anticancer and antibacterial drugs. Chemistry & Biology 17 (5): 421–433.
[3]Pang, B., et al. (2013). Drug-induced histone eviction from open chromatin contributes to the chemotherapeutic effects of doxorubicin. Nature Communications 4 (5): 1908
[4]Boucek RJ., et al. (1987). The major metabolite of doxorubicin is a potent inhibitor of membrane-associated ion pumps. A correlative study of cardiac muscle with isolated membrane fractions. J of Biol Chem 262: 15851-15856.

Product Citation

Chemical Properties

Physical AppearanceA solid
StorageStore at 4°C
M.Wt543.52
Cas No.23214-92-8
FormulaC27H29NO11
SynonymsAdriamycin, Doxil, Adriablastin, Doxorubicinum, Myocet
Solubility≥27.2 mg/mL in DMSO; insoluble in EtOH; ≥24.8 mg/mL in H2O with ultrasonic
Chemical Name(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
SDFDownload SDF
Canonical SMILESCC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O
Shipping ConditionSmall Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips We do not recommend long-term storage for the solution, please use it up soon.

Protocol

Cell experiment [1]:

Cell lines

MDA-MB-231 cells

Preparation method

This compound is soluble in DMSO. General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20 ℃ for several months.

Reaction Conditions

20 nM; 72 hrs

Applications

In MDA-MB-231 cells, SH003 at 120 μg/mL with Doxorubicin at 20 nM showed a synergistic effect.

Animal experiment [2]:

Animal models

Female athymic nude mice injected s.c. with MB231 cells

Dosage form

3 mg/kg/day; delivered intratumorly

Applications

Doxorubicin in combination with adenoviral MnSOD (AdMnSOD) plus 1,3-bis(2-chloroethyl)-1-nitrosourea (BCNU) showed the greatest effect in decreasing the volumes of MB231 tumors and prolonging survival of mice.

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]. Woo SM, Kim AJ, Choi YK, Shin YC, Cho SG, Ko SG. Synergistic Effect of SH003 and Doxorubicin in Triple-negative Breast Cancer. Phytother Res. 2016 Aug 1.

[2]. Sun W, Kalen AL, Smith BJ, Cullen JJ, Oberley LW. Enhancing the antitumor activity of adriamycin and ionizing radiation. Cancer Res. 2009 May 15;69(10):4294-300.

Biological Activity

Description Doxorubicin (Adriamycin) is an antibiotic agent, inhibitor of DNA topoisomerase II and inducer of DNA damage and apoptosis.
Targets Autophagy          
IC50            

Quality Control

Chemical structure

Doxorubicin

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