Doxorubicin hydrochloride

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Cat.No. 2252 - Doxorubicin hydrochloride | C27H29NO11.HCl | CAS No. 25316-40-9
Description: Antitumor antibiotic agent. Inhibits DNA topoisomerase II
Alternative Names: Adriamycin, NSC 123127
Chemical Name: 10-[(3-Amino-2,3,6-trideoxy-α-L-lyxohexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-5,12-naphthacenedione hydrochloride
Purity: ≥98% (HPLC)
Datasheet
Citations (19)
Reviews (1)
Literature

Biological Activity

Antitumor antibiotic agent that inhibits DNA topoisomerase II. DNA intercalator that inhibits nucleic acid synthesis and induces apoptosis. Reduces intracellular tau levels.

Compound Libraries

Doxorubicin hydrochloride is also offered as part of the Tocriscreen Plus and Tocriscreen Library of FDA-Approved Compounds. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 579.99
Formula C27H29NO11.HCl
Storage Desiccate at RT
Purity ≥98% (HPLC)
CAS Number 25316-40-9
PubChem ID 443939
InChI Key MWWSFMDVAYGXBV-RUELKSSGSA-N
Smiles OC1=C(C[C@]([C@](CO)=O)(O)C[C@@H]4O[C@@]5([H])C[C@H](N)[C@H](O)[C@H](C)O5)C4=C(O)C3=C1C(C2=CC=CC(OC)=C2C3=O)=O.Cl

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
water 29 50
DMSO 29 50

Preparing Stock Solutions

The following data is based on the product molecular weight 579.99. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.5 mM 3.45 mL 17.24 mL 34.48 mL
2.5 mM 0.69 mL 3.45 mL 6.9 mL
5 mM 0.34 mL 1.72 mL 3.45 mL
25 mM 0.07 mL 0.34 mL 0.69 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References

References are publications that support the biological activity of the product.

Skladanowski and Konopa (1993) Adriamycin and daunomycin induce programmed cell death (apoptosis) in tumour cells. Biochem.Pharmacol. 46 357 PMID: 8347161

Patel et al (1997) Identification of yeast DNA topoisomerase II mutants resistant to the antitumor drug doxorubicin: implications for the mechanisms of doxorubicin action and cyotoxicity. Mol.Pharmacol. 52 658 PMID: 9380029

Gewirtz (1999) A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin. Biochem.Pharmacol. 57 727 PMID: 10075079

Dickey et al (2006) Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression. Mol.Neurodegen. 1 6 PMID: 16930453


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View Related Products by Product Action

View all DNA Topoisomerase Inhibitors

Keywords: Doxorubicin hydrochloride, Doxorubicin hydrochloride supplier, Antitumor, antibiotics, agent, inhibitors, inhibits, DNA, topoisomerase, II, Isomerases, NSC123127, chemotherapeutics, Adriamycin, NSC, 123127, Topoisomerase, Apoptosis, Inducers, Antibiotics, 2252, Tocris Bioscience

⚠ WARNING: This product can expose you to chemicals including Doxorubicin hydrochloride (Adriamycin), which is known to the State of California to cause cancer. For more information, go to www.P65Warnings.ca.gov

19 Citations for Doxorubicin hydrochloride

Citations are publications that use Tocris products. Selected citations for Doxorubicin hydrochloride include:

Iriondo (2018) TAK1 mediates microenvironment-triggered autocrine signals and promotes triple-negativebreast cancer lung metastasis. Nat Commun 9 1994 PMID: 29777109

Yuan et al (2017) Tenovin-6 impairs autophagy by inhibiting autophagic flux. Cell Death Dis 8 e2608 PMID: 28182004

Ayoub (2017) Crizotinib, a MET inhibitor, inhibits growth, migration, and invasion of breast cancer cells in vitro and synergizes with chemotherapeutic agents. Onco Targets Ther 10 4869 PMID: 29042798

Smyth et al (2015) Biodistribution and delivery efficiency of unmodified tumor-derived exosomes. J Control Release 199 145 PMID: 25523519

Montgomery (2017) An Alpha-1A Adrenergic Receptor Agonist Prevents Acute Doxorubicin Cardiomyopathy in Male Mice. Plos One 12 e0168409 PMID: 28081170

El Zawily (2017) The EphB6 receptor is overexpressed in pediatric T cell acute lymphoblastic leukemia and increases its sensitivity to doxorubicin treatment. Sci Rep 7 14767 PMID: 29116180

Sundaresan et al (2014) Dual-responsive polymer-coated iron oxide nanoparticles for drug delivery and imaging applications. Int J Pharm 466 1 PMID: 24607216

Lim et al (2008) B cell translocation gene 2 enhances susceptibility of HeLa cells to doxorubicin-induced oxidative damage. J Biol Chem 283 33110 PMID: 18840609

Bussey et al (2016) Targeting polo-like kinase 1, a regulator of p53, in the treatment of adrenocortical carcinoma. PLoS One 5 1 PMID: 26754547

Thomas et al (2016) The α-1A Adrenergic Receptor in the Rabbit Heart. Mol Syst Biol 11 e0155238 PMID: 27258143

Hayano et al (2016) Loss of cysteinyl-tRNA synthetase (CARS) induces the transsulfuration pathway and inhibits ferroptosis induced by cystine deprivation. Cell Death Differ 23 270 PMID: 26184909

Aho et al (2016) Extracellular ATP protects endothelial cells against DNA damage. Purinergic Signal 12 575 PMID: 27030122

Thomas et al (2016) A Myocardial Slice Culture Model Reveals Alpha-1A-Adrenergic Receptor Signaling in the Human Heart. JACC Basic Transl Sci 1 155 PMID: 27453955

Natrajan et al (2012) Functional characterization of the 19q12 amplicon in grade III breast cancers. Breast Cancer Res 14 R53 PMID: 22433433

Gligorich et al (2013) Development of a screen to identify selective small molecules active against patient-derived metastatic and chemoresistant breast cancer cells. Breast Cancer Res 15 R58 PMID: 23879992

Zhitomirsky and Assaraf (2015) Lysosomal sequestration of hydrophobic weak base chemotherapeutics triggers lysosomal biogenesis and lysosome-dependent cancer multidrug resistance. Clin Transl Med 6 1143 PMID: 25544758

Gharanei et al (2013) Attenuation of doxorubicin-induced cardiotoxicity by mdivi-1: a mitochondrial division/mitophagy inhibitor. PLoS One 8 e77713 PMID: 24147064

Toldo et al (2013) Comparative cardiac toxicity of anthracyclines in vitro and in vivo in the mouse. PLoS One 8 e58421 PMID: 23516478

Robinson et al (2013) RB1 status in triple negative breast cancer cells dictates response to radiation treatment and selective therapeutic drugs. PLoS One 8 e78641 PMID: 24265703


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Reviews for Doxorubicin hydrochloride

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2uM Doxorubicin damaged NRVM cells in 12 hr
By Anonymous on 12/12/2017
Assay Type: In Vitro
Species: Rat
Cell Line/Tissue: Heart myocyte

Used 2uM Doxorubicin hydrochloride to treat Neonatal rat ventricular myocytes for 12 hr to 24 hr, see clear effect of cell damage.

PMID: 28286875

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Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis
Cell Cycle & DNA Damage Repair

Cell Cycle & DNA Damage Repair Poster

In normal cells, each stage of the cell cycle is tightly regulated, however in cancer cells many genes and proteins that are involved in the regulation of the cell cycle are mutated or over expressed. Adapted from the 2015 Cancer Product Guide, Edition 3, this poster summarizes the stages of the cell cycle and DNA repair. It also highlights strategies for enhancing replicative stress in cancer cells to force mitotic catastrophe and cell death.