Doxorubicin (hydrochloride)

Doxorubicin hydrochloride (Hydroxydaunorubicin hydrochloride; ADR), a cytotoxic anthracycline antibiotic, is an anti-cancer chemotherapy agent. Doxorubicin hydrochloride is a potent human DNA topoisomerase I and topoisomerase II inhibitor with IC50s of 0.8 μM and 2.67 μM, respectively. Doxorubicin hydrochloride reduces basal phosphorylation of AMPK and its downstream target acetyl-CoA carboxylase. Doxorubicin hydrochloride induces apoptosis and autophagy[1][2][3].

Product Specifications

CAS Number

[25316-40-9]

Product Name Alternative

Hydroxydaunorubicin (hydrochloride) ; ADR

UNSPSC

12352005

Hazard Statement

H302, H340, H350, H360

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-hydrochloride.html

Purity

99.90

Solubility

DMSO : 25 mg/mL (ultrasonic; warming; heat to 60°C) |H2O : 50 mg/mL (ultrasonic; warming; heat to 60°C)

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.[H]Cl

Molecular Formula

C27H30ClNO11

Molecular Weight

579.98

Precautions

H302, H340, H350, H360

References & Citations

[1]John L. Nitiss, et al. Targeting DNA topoisomerase II in cancer chemotherapy.Nat Rev Cancer. 2009 May;9 (5) :338-50.|[2]Hee-KyungRhee, et al. Synthesis, cytotoxicity, and DNA topoisomerase II inhibitory activity of benzofuroquinolinediones. Bioorg Med Chem. 2007 Feb 15;15 (4) :1651-8.|[3]P D Foglesong, et al. Doxorubicin inhibits human DNA topoisomerase I. Cancer Chemother Pharmacol. 1992;30 (2) :123-5.|[4]Nesstor Pilco-Ferreto, et al. Influence of doxorubicin on apoptosis and oxidative stress in breast cancer cell lines. Int J Oncol. 2016 Aug;49 (2) :753-62.|[5]Regine Lüpertz, et al. Dose- and time-dependent effects of doxorubicin on cytotoxicity, cell cycle and apoptotic cell death in human colon cancer cells. Toxicology. 2010 May 27;271 (3) :115-21.|[6]Penelope D Ottewell, et al. Antitumor effects of doxorubicin followed by zoledronic acid in a mouse model of breast cancer. J Natl Cancer Inst. 2008 Aug 20;100 (16) :1167-78.|[7]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|[8]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.|[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]Pecoraro M, et al. Inflammatory mediators in a short-time mouse model of doxorubicin-induced cardiotoxicity. Toxicol Appl Pharmacol. 2016 Feb 15;293:44-52.|[11]Sun X, et al. Qiliqiangxin improves cardiac function and attenuates cardiac remodelling in doxorubicin-induced heart failure rats. Pharm Biol. 2020 Dec;58 (1) :417-426.