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Doxorubicin

In stock
Catalog No.
A3966
Topo II inhibitor,immunosuppresive antineoplastic antibiotic
Grouped product items
SizePriceStock Qty
10mM (in 1mL DMSO)
$70.00
In stock
Evaluation Sample
$28.00
In stock
10mg
$50.00
In stock
25mg
$70.00
In stock
100mg
$160.00
In stock

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Background

Doxorubicin is a semi-synthesized anticancer agent derived from bacterial culture. [1] It is an anthracycline antibiotic. It is been widely used in blood cancers, solid tumors and sarcomas.

Doxorubicin intercalates into DNA double strand and inhibits the progression of DNA topoisomerase II, stopping replication process. [2] Doxorubicin also induces histone eviction from open chromatin, causing DNA damage and epigenetic deregulation. [3]

Doxorubicin is administrated intravenously. Approximately 75% of doxorubicin and its metabolites bind to plasma protein. Doxorubicin does not cross blood brain barrier. 50% of the drug is eliminated unchanged from the body mainly though bile excretion. The remaining undergoes one-electron reduction, two-electron reduction, and deglycosidation. The major metabolite is a potent membrane ion pump inhibitor, which is associated with cardiomyopathy. [4]

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 RT
M.Wt543.52
Cas No.23214-92-8
FormulaC27H29NO11
SynonymsAdriamycin, Doxil, Adriablastin, Doxorubicinum, Myocet
Solubility≥27.2 mg/mL in DMSO, <2.17 mg/mL 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 ConditionEvaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tipsFor 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.

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

Related Biological Data

Doxorubicin
Cells were incubated with YSK-MEND for 24h, and then trypsinized and reseeded in 24-well plates. 24 h after reseeding, the cells were washed with PBS and incubated with DOX-containing medium for 6h. DOX-containing medium was removed, and cells were washed with PBS and recovered 18 h after fresh medium incubation. Protein concentrations determined by the CA method were regarded as a viability. Values indicate mRNA expression relative to nontreatment (NT) ± SD.

Related Biological Data

Doxorubicin

Related Biological Data

Doxorubicin