Duocarmycin SA
[CAS# 130288-24-3]

Identification

• Classification: API >> Antineoplastic agents
• Name: Duocarmycin SA
• Synonyms: (+)-Duocarmycin SA; Antibiotic DC 113
• Molecular Formula: C₂₅H₂₃N₃O₇
• Molecular Weight: 477.47
• CAS Registry Number: 130288-24-3
• SMILES: COC1=C(C(=C2C(=C1)C=C(N2)C(=O)N3C[C@H]4C[C@@]45C3=CC(=O)C6=C5C=C(N6)C(=O)OC)OC)OC

Properties

• Solubility: 27.79 mg/L (25 °C water)
• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.711, Calc.^*
• Melting point: 281.91 °C
• Boiling Point: 787.7±60.0 °C (760 mmHg), Calc.^*, 648.39 °C
• Flash Point: 430.2±32.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H302-H340-H350-H360
• Safety Statements: P201-P202-P264-P270-P280-P301+P312+P330-P308+P313-P405-P501

Discovery and Applications

Duocarmycin SA is a potent cytotoxic compound derived from the natural product duocarmycin. It was first isolated from the bacterium Streptomyces antibioticus in the 1970s. The discovery of duocarmycin SA was a result of screening microbial extracts for compounds with antitumor activity. Its unique chemical structure and mechanism of action make it a promising candidate for cancer therapy.

Duocarmycin SA is a DNA alkylating agent that selectively targets and binds to the minor groove of DNA, leading to irreversible DNA damage and cell death. It has shown potent antitumor activity against a variety of cancer cell lines in preclinical studies, including lung, breast, and prostate cancers. Duocarmycin SA is being investigated for its potential in the treatment of solid tumors and hematological malignancies. Additionally, efforts are underway to develop novel drug delivery strategies to improve the therapeutic index of duocarmycin SA and minimize off-target toxicity.

References

Trzupek et al.. Alkylation of duplex DNA in nucleosome core particles by duocarmycin SA and yatakemycin, Nature Chemical Biology, 2006