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Doxorubicin (Adriamycin) HCl (Synonyms: DOX)

Katalog-Nr.GC17567

Doxorubicin (Hydroxydaunorubicin) Hydrochlorid, ein zytotoxisches Anthracyclin-Antibiotikum, ist ein Chemotherapeutikum zur Behandlung von Krebs.

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Doxorubicin (Adriamycin) HCl Chemische Struktur

Cas No.: 25316-40-9

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10mM (in 1mL DMSO)
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10mM (in 1mL Water)
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500mg
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Sample solution is provided at 25 µL, 10mM.

Product has been cited by 2 publications

Product Documents

Quality Control & SDS

View current batch:

Protocol

Cell experiment: [1]

Cell lines

H9c2 cells

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.

Reaction Conditions

1 μg/ml, 2 hours

Applications

H9c2 cells were treated with increased concentrations of Doxorubicin (0.1, 0.3, 0.5, and 1.0 μg/ml, equal to 0.17, 0.52, 0.85, and 1.71 μM separately) for 2 h, or treated with 0.3 μg/ml (equal to 0.52 μM) of Doxorubicin for the different time points. Doxorubicin induces strong AMPKα (Thr 172) and its downstream Acetyl-CoA carboxylase (ACC, Ser 79) phosphorylation in both time- and dose-dependent manner. AMPKα phosphorylation became obvious after 1 h of Doxorubicin treatment which was further sustained for at least 6 h. LKB1, the possible upstream kinase for AMPK, was also activated by Doxorubicin in H9c2 cells.

Animal experiment: [2]

Animal models

C57BL/10 mice

Dosage form

Intraperitoneal injection, 20 mg/kg

Applications

Five days after doxorubicin injection, mice displayed significantly impaired systolic (LVP, -29%; dP/dtmax, -45%), diastolic (dP/dtmin, -44%; stiffness, +275%), and global (SV, -61%; HR, -18%; CO,-68%) left ventricular (LV) function when compared with the placebo group. Both cardiac lipid peroxidation activity (+37%) and cardiac nitrotyrosine protein expression (+204%) were increased when compared with placebo 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] Chen M B, Wu X Y, Gu J H, et al. Activation of AMP-activated protein kinase contributes to doxorubicin-induced cell death and apoptosis in cultured myocardial H9c2 cells. Cell biochemistry and biophysics, 2011, 60(3): 311-322.

[2] Riad A, Bien S, Westermann D, et al. Pretreatment with statin attenuates the cardiotoxicity of Doxorubicin in mice. Cancer research, 2009, 69(2): 695-699.

Background

Doxorubicin ist ein halbsynthetisches Antikrebsmittel, das aus einer bakteriellen Kultur gewonnen wird. [1] Es handelt sich um ein Anthracyclin-Antibiotikum. Es wird weit verbreitet bei Blutkrebs, soliden Tumoren und Sarkomen eingesetzt.

Doxorubicin interkaliert in die DNA-Doppelstränge und hemmt den Fortschritt der DNA-Topoisomerase II, was den Replikationsprozess stoppt. Doxorubicin verursacht auch eine Auslagerung von Histonen aus offenem Chromatin, was zu DNA-Schäden und epigenetischer Deregulierung führt.

Doxorubicin wird intravenös verabreicht. Etwa 75% von Doxorubicin und seinen Metaboliten binden an Plasmaproteine. Doxorubicin überwindet nicht die Blut-Hirn-Schranke. 50% des Arzneimittels werden unverändert aus dem Körper ausgeschieden, hauptsächlich durch Gallenausscheidung. Der Rest unterliegt einer Ein-Elektron-Reduktion, Zwei-Elektron-Reduktion und Deglykosidierung. Das wichtigste Stoffwechselprodukt ist ein potenter Membran-Ionenpumpen-Inhibitor, der mit Kardiomyopathie assoziiert ist. [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.

Chemical Properties

Cas No. 25316-40-9 SDF
Überlieferungen DOX
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;hydrochloride
Canonical 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)CO)O)N)O.Cl
Formula C27H29NO11.HCl M.Wt 579.98
Löslichkeit 33.3mg/ml in Water(Need ultrasonic);DMSO : >20 mg/mL (34.48 mM; Need ultrasonic) Storage 4°C, protect from light
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 1.7242 mL 8.621 mL 17.242 mL
5 mM 0.3448 mL 1.7242 mL 3.4484 mL
10 mM 0.1724 mL 0.8621 mL 1.7242 mL
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Related Video

    Doxorubicin (Adriamycin) HCl- GlpBio

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