MMAF-Ome
[CAS# 863971-12-4]

Identification

• Name: MMAF-Ome
• Synonyms: methyl (2S)-2-[[(2R,3R)-3-methoxy-3-[(2S)-1-[(3R,4S,5S)-3-methoxy-5-methyl-4-[methyl-[(2S)-3-methyl-2-[[(2S)-3-methyl-2-(methylamino)butanoyl]amino]butanoyl]amino]heptanoyl]pyrrolidin-2-yl]-2-methylpropanoyl]amino]-3-phenylpropanoate
• Molecular Formula: C₄₀H₆₇N₅O₈
• Molecular Weight: 745.99
• CAS Registry Number: 863971-12-4
• SMILES: CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@@H]([C@@H](C)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)OC)OC)OC)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.513, Calc.^*
• Boiling Point: 871.8±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 481.0±34.3 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS0i7 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

MMAF-Ome is a powerful compound with many applications. Driven by the urgent need for more effective cancer treatments, researchers look for molecules that can selectively target and kill cancer cells while sparing healthy tissue. Through a series of chemical transformations and utilizing structure-activity relationship studies, MMAF-Ome emerged as a promising candidate. By binding to tubulin, a key component of microtubules, MMAF-Ome interferes with the assembly and stability of these cellular structures, leading to cell cycle arrest and ultimately cell death. It is expected to minimize off-target effects and improve treatment outcomes.

MMAF-Ome's potential therapeutic applications are not limited to cancer treatment. Its cytotoxic properties make it a candidate for the treatment of a range of diseases characterized by abnormal cell proliferation, including certain types of leukemias, lymphomas and solid tumors. Additionally, studies are exploring its efficacy in combination therapies, where MMAF-Ome may enhance the effectiveness of existing therapies or overcome resistance mechanisms. In addition to direct therapeutic applications, MMAF-Ome has contributed to advances in drug delivery technology. Formulation that incorporates MMAF-Ome into targeted drug delivery systems has the potential to increase drug efficacy, reduce systemic toxicity, and improve patient outcomes. By encapsulating MMAF-Ome in nanoparticles or antibody-drug conjugates, researchers can deliver the compound directly to tumor cells while minimizing contact with healthy tissue.

References

2022. Discovery and Development of Dolastatin 10-Derived Antibody Drug Conjugate Anticancer Drugs. Journal of Natural Products, 85(1).
DOI: 10.1021/acs.jnatprod.1c01135