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 (9)
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.

All Tocris products are intended for laboratory research use only.

Solubility Data

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

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.72 mL 8.62 mL 17.24 mL
5 mM 0.34 mL 1.72 mL 3.45 mL
10 mM 0.17 mL 0.86 mL 1.72 mL
50 mM 0.03 mL 0.17 mL 0.34 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

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


If you know of a relevant reference for Doxorubicin hydrochloride, please let us know.

View Related Products by Product Action

View all DNA Topoisomerase Inhibitors

Keywords: Antitumor antibiotics agent inhibitors inhibits DNA topoisomerase II Isomerases NSC123127 chemotherapeutics Adriamycin NSC 123127 DNA Topoisomerase

9 Citations for Doxorubicin hydrochloride

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

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

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

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

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

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

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

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


Do you know of a great paper that uses Doxorubicin hydrochloride from Tocris? If so please let us know.

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Literature in this Area

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.

Pathways for Doxorubicin hydrochloride

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