Doxorubicin
Doxorubicin (Hydroxydaunorubicin), a broad-spectrum anthracycline antibiotic with cytotoxic properties, is an anti-cancer chemotherapy agent. Doxorubicin has fluorescence properties. Doxorubicin inhibits topoisomerase II with an IC50 of 2.67 μM, thus stopping DNA replication. Doxorubicin reduces basal phosphorylation of AMPK and its downstream target acetyl-CoA carboxylase. Doxorubicin induces apoptosis and autophagy[1][2]. Doxorubicin inhibits human DNA topoisomerase I with an IC50 of 0.8 μM[3].
Product Specifications
CAS Number
[23214-92-8]
Product Name Alternative
Hydroxydaunorubicin
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
ADC Payload; AMPK; Antibiotic; Apoptosis; Autophagy; Bacterial; Fluorescent Dye; HBV; HIV; Mitophagy; Topoisomerase
Type
Natural Products
Related Pathways
Antibody-drug Conjugate/ADC Related; Anti-infection; Apoptosis; Autophagy; Cell Cycle/DNA Damage; Epigenetics; Others; PI3K/Akt/mTOR
Applications
Cancer-Kinase/protease
Field of Research
Cancer; Infection
Assay Protocol
https://www.medchemexpress.com/Doxorubicin.html
Purity
98.60
Solubility
10 mM in DMSO
Smiles
COC1=C2C(C(C(C(O)=C(C[C@](C(CO)=O)(O)C[C@@H]3O[C@@]4([H])C[C@H](N)[C@H](O)[C@H](C)O4)C3=C5O)=C5C2=O)=O)=CC=C1
Molecular Formula
C27H29NO11
Molecular Weight
543.52
Precautions
H302, H315, H319, H335
References & Citations
[1]Nitiss JL, et al. Targeting DNA topoisomerase II in cancer chemotherapy.Nat Rev Cancer. 2009 May;9 (5) :338-50.|[2]Rhee HK, et al. Synthesis, cytotoxicity, and DNA topoisomerase II inhibitory activity of benzofuroquinolinediones. Bioorg Med Chem. 2007 Feb 15;15 (4) :1651-8.|[3]Foglesong PD, et al. Doxorubicin inhibits human DNA topoisomerase I. Cancer Chemother Pharmacol. 1992;30 (2) :123-5.|[4]Sadeghi-Aliabadi H, et al. Cytotoxic evaluation of doxorubicin in combination with simvastatin against human cancer cells. Res Pharm Sci. 2010 Jul;5 (2) :127-33.|[5]El-Zawahry A, et al. Doxorubicin increases the effectiveness of Apo2L/TRAIL for tumor growth inhibition of prostate cancerxenografts. BMC Cancer. 2005 Jan 7;5:2.|[6]Hayward R, et al. Doxorubicin cardiotoxicity in the rat: an in vivo characterization. J Am Assoc Lab Anim Sci. 2007 Jul;46 (4) :20-32.|[7]Johansson S, et al. Elimination of HIV-1 infection by treatment with a doxorubicin-conjugated anti-envelope antibody. AIDS. 2006;20 (15) :1911-1915.|[8]Koda LY, Van der Kooy D. Doxorubicin: a fluorescent neurotoxin retrogradely transported in the central nervous system. Neurosci Lett. 1983 Mar 28;36 (1) :1-8. doi: 10.1016/0304-3940 (83) 90476-7. PMID: 6190113. 9|[9]Mirza A Z, Shamshad H. Preparation and characterization of doxorubicin functionalized gold nanoparticles[J]. European journal of medicinal chemistry, 2011, 46 (5) : 1857-1860.|[10]Kauffman MK, Kauffman ME, Zhu H, Jia Z, Li YR. Fluorescence-Based Assays for Measuring Doxorubicin in Biological Systems. React Oxyg Species (Apex) . 2016;2 (6) :432-439. doi: 10.20455/ros.2016.873. PMID: 29707647; PMCID: PMC5921830.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, sealed storage, away from moisture and light)
Scientific Category
Natural Products
Clinical Information
Launched
Isoform
Daunorubicins/Doxorubicins; HIV-1; Topo I; Topo II
Citation 01
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