Doxorubicin

- Overview
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    Background
    
    Doxorubicin is a semi-synthesized anticancer agent derived from bacterial culture. [1] It is an anthracycline antibiotic. It is been widely used in blood cancers, solid tumors and sarcomas.
    Doxorubicin intercalates into DNA double strand and inhibits the progression of DNA topoisomerase II, stopping replication process. [2] Doxorubicin also induces histone eviction from open chromatin, causing DNA damage and epigenetic deregulation. [3]
    Doxorubicin is administrated intravenously. Approximately 75% of doxorubicin and its metabolites bind to plasma protein. Doxorubicin does not cross blood brain barrier. 50% of the drug is eliminated unchanged from the body mainly though bile excretion. The remaining undergoes one-electron reduction, two-electron reduction, and deglycosidation. The major metabolite is a potent membrane ion pump inhibitor, which is associated with cardiomyopathy. [4]
    
    [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.
- Properties
  - Categories
    
    Topo II inhibitor, immunosuppresive antineoplastic antibiotic
    
    Alternative Name
    
    Adriamycin, Doxil, Adriablastin, Doxorubicinum, Myocet; (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
    
    CAS Number
    
    23214-92-8
    
    Molecular Formula
    
    C27H29NO11
    
    Molecular Weight
    
    543.52
    
    Appearance
    
    A solid
    
    Purity
    
    99.09%
    
    Solubility
    
    ≥27.2 mg/mL in DMSO; insoluble in EtOH; ≥24.8 mg/mL in H2O with ultrasonic
    
    Storage
    
    Powder: Store at RT; Solution: Store at -20°C
    
    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
    
    * For Research Use Only
- Reference
  - 1. Ji Yun Lee, Joo Hyun Kim, et al. "EGR1 as a potential marker of prognosis in extranodal NK/T-cell lymphoma." Sci Rep. 2021 May 14;11(1):10342. PMID:33990633
    2. Zhongying Gong, Xiaoying Liu, et al. "Tumor acidic microenvironment-induced drug release of RGD peptide nanoparticles for cellular uptake and cancer therapy." Colloids Surf B Biointerfaces. 2021 Mar 4;202:111673. PMID:33714186
    3. Wang X, Wang Q, et al. "TFEB-NF-κB inflammatory signaling axis: a novel therapeutic pathway of Dihydrotanshinone I in doxorubicin-induced cardiotoxicity." J Exp Clin Cancer Res. 2020;39(1):93. PMID:32448281
    4. Gong Z, Lao J, et al. "pH-Triggered geometrical shape switching of a cationic peptide nanoparticle for cellular uptake and drug delivery." Colloids Surf B Biointerfaces. 2020;188:110811. PMID:31982793
    5. Qi W, Boliang W, et al. "Cardamonin protects against doxorubicin-induced cardiotoxicity in mice by restraining oxidative stress and inflammation associated with Nrf2 signaling." Biomed Pharmacother. 2020;122:109547. PMID:31918264
    6. Gong Z, Shi Y, et al. "Plasma Amine Oxidase-Induced Nanoparticle-to-Nanofiber Geometric Transformation of an Amphiphilic Peptide for Drug Encapsulation and Enhanced Bactericidal Activity." ACS Appl Mater Interfaces. 2020;12(4):4323–4332. PMID:31899611
    7. Gong Z, Liu X, Wu J, et al. "pH-triggered morphological change in a self-assembling amphiphilic peptide used as an antitumor drug carrier." Nanotechnology. 2020;31(16):165601. PMID:31891937
    8. Yan L, Ding B, et al. "Inhibition of SMYD2 suppresses tumor progression by down-regulating microRNA-125b and attenuates multi-drug resistance in renal cell carcinoma." Theranostics. 2019 Oct 22;9(26):8377-8391. PMID:31754403
    9. Wang Z, Chen J, et al. "cGAS/STING axis mediates a topoisomerase II inhibitor-induced tumor immunogenicity." J Clin Invest. 2019 Aug 13;130:4850-4862. PMID:31408442
    10. Wang X, Li C, et al. "Tanshinone IIA Restores Dynamic Balance of Autophagosome/Autolysosome in Doxorubicin-Induced Cardiotoxicity via Targeting Beclin1/LAMP1." Cancers (Basel). 2019 Jun 28;11(7). pii: E910. PMID:31261758
    11. Zhang Y, Xia F, et al. "miR-135b-5p enhances doxorubicin-sensitivity of breast cancer cells through targeting anterior gradient 2." J Exp Clin Cancer Res. 2019 Jan 21;38(1):26. PMID:30665445
    12. Goodspeed A, Jean A, et al. "A Whole-genome CRISPR Screen Identifies a Role of MSH2 in Cisplatin-mediated Cell Death in Muscle-invasive Bladder Cancer." Eur Urol. 2019 Feb;75(2):242-250. PMID:30414698
    13. Deng Y, Li F, et al. "Triptolide sensitizes breast cancer cells to Doxorubicin through the DNA damage response inhibition." Mol Carcinog. 2018 Jun;57(6):807-814. PMID:29500880