2,3-Dihydro-5,8-dihydroxy-1,4-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione
[CAS# 70476-74-3]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Anthracenes
• Name: 2,3-Dihydro-5,8-dihydroxy-1,4-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione
• Synonyms: 5,8-bis[2-(2-hydroxyethylamino)ethylimino]-6,7-dihydroanthracene-1,4,9,10-tetrol
• Molecular Formula: C₂₂H₃₀N₄O₆
• Molecular Weight: 446.50
• CAS Registry Number: 70476-74-3
• SMILES: C1CC(=NCCNCCO)C2=C(C3=C(C=CC(=C3C(=C2C1=NCCNCCO)O)O)O)O

Properties

• Solubility: Very slightly soluble (0.54 g/L) (25 ºC), Calc.^*
• Density: 1.43±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Boiling point: 771.4±60.0 ºC (760 Torr), Calc.^*
• Flash point: 420.3±32.9 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2021 ACD/Labs)

Discovory and Applicatios

2,3-Dihydro-5,8-dihydroxy-1,4-bis[[2-[(2-hydroxyethyl)amino]ethyl]amino]-9,10-anthracenedione, commonly known as Doxorubicin, was discovered in the 1960s during a systematic exploration of anthracycline derivatives for their anticancer properties. Chemists synthesized a series of anthracycline compounds and evaluated their cytotoxic effects on cancer cells. Among these compounds, Doxorubicin emerged as a potent anticancer agent with remarkable efficacy against various types of cancer, including leukemia, lymphoma, breast cancer, and lung cancer. Its discovery revolutionized cancer chemotherapy and paved the way for the development of anthracycline-based chemotherapeutic agents.

Doxorubicin is widely used in cancer chemotherapy regimens as a first-line or adjuvant treatment for various solid tumors and hematological malignancies. It inhibits DNA replication and RNA synthesis by intercalating into DNA strands, leading to DNA damage and cell death. Its broad-spectrum anticancer activity makes it effective against a wide range of cancers. Doxorubicin is often combined with other anticancer drugs or radiation therapy to enhance treatment efficacy and reduce the risk of drug resistance. Combination regimens, such as CHOP (cyclophosphamide, doxorubicin, vincristine, and prednisone), are commonly used in the treatment of lymphomas and solid tumors.

Despite its efficacy in cancer treatment, Doxorubicin can cause cardiotoxicity, leading to irreversible damage to cardiac tissues and heart failure. Research is underway to develop strategies to mitigate Doxorubicin-induced cardiotoxicity, including the use of cardioprotective agents or liposomal formulations to reduce cardiac exposure to the drug. Liposomal formulations of Doxorubicin, such as Doxil and Myocet, encapsulate the drug within lipid vesicles, allowing for targeted delivery to tumor tissues while reducing systemic toxicity and cardiotoxicity. These formulations enhance the therapeutic index of Doxorubicin and improve patient tolerance to treatment.

Researchers are exploring targeted therapies that selectively deliver Doxorubicin to cancer cells while sparing normal tissues, thereby minimizing side effects. These strategies involve conjugating Doxorubicin to targeting ligands or nanoparticles that recognize cancer-specific biomarkers or tumor microenvironments. Doxorubicin is widely used in laboratory research to study mechanisms of cancer cell death, drug resistance, and DNA damage repair. It serves as a valuable tool for elucidating molecular pathways involved in cancer progression and identifying potential targets for therapeutic intervention.