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| | MonoMethylauristatin F Basic information | | in vivo |
| Product Name: | MonoMethylauristatin F | | Synonyms: | MMAF;MonoMethylauristatin F;MonoMethyl Auristatin F | MMAF;MMAF
(MonoMethylauristatin F);Monomethyl auristatin phenylalanine;MONOMETHYLAURISTATIN F; MMAF; MONOMETHYL AURISTATIN PHENYLALANINE; 745017-94-1;(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-phenylpropanoic acid;(2S)-2-[[(2R,3R)-3-methoxy-3-[(2S)-1-[(3R,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-phenylpropanoic acid | | CAS: | 745017-94-1 | | MF: | C39H65N5O8 | | MW: | 731.96 | | EINECS: | | | Product Categories: | ADCs | | Mol File: | 745017-94-1.mol |  |
| | MonoMethylauristatin F Chemical Properties |
| Boiling point | 896.8±65.0 °C(Predicted) | | density | 1.116±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | solubility | Soluble in DMSO | | form | A solid | | pka | 3.56±0.10(Predicted) | | Stability: | Hygroscopic |
| | MonoMethylauristatin F Usage And Synthesis |
| in vivo | The maximum tolerated dose in mice of MMAF (Monomethylauristatin F) (>16 mg/kg) is much higher than MMAF (Monomethylauristatin F) (1 mg/kg). cAC10-L1-MMAF4 has an MTD of 50 mg/kg in mice and 15 mg/kg in rats. The corresponding cAC10-L4-MMAF4 ADC was much less toxic, having MTDs in mice and rats of >150 mg/ kg and 90 mg/kg in rats, respectively. | | Description | MMAF (Monomethylauristatin F) is an effective tubulin polymerization inhibitor, used as an anti-tumor drug. MMAF (Monomethylauristatin F) is widely used as the cytotoxic component of antibody-conjugated drugs (ADCs), such as Vorsetuzumab mafodotin and SGN-CD19A. | | Uses | Monomethyl Auristatin F is an antimicrotubule agent. A potent mitotic inhibitor. | | Biological Activity | MMAF (Monomethylauristatin F) is a potent tubulin polymerization inhibitor and is used as a antitumor agent. MMAF (Monomethylauristatin F) is widely used as a cytotoxic component of antibody-drug conjugates (ADCs) such as vorsetuzumab mafodotin and SGN-CD19A. | | Biotechnological Applications | MMAF is a new auristatin derivative with a charged C-terminal phenylalanine that attenuates its cytotoxic activity compared to its uncharged counterpart, Monomethyl auristatin E (MMAE). Because of MMAF is highly toxic, it cannot be used as a drug itself. MMAF induces potent antitumor effects when conjugated via protease cleavable linkers to a monoclonal antibody targeting internalizing, tumor-specific cell surface antigens. The linker to the monoclonal antibody is stable in extracellular fluid, but is cleaved by cathepsin once the conjugate has entered a tumor cell, thus activating the anti-mitotic mechanism. | | in vitro | MMAF inhibits anaplastic large cell lymphoma Karpas 299, breast carcinoma H3396, renal cell carcinoma 786-O and Caki-1 cells with IC50s of 119, 105, 257 and 200 nM in vitro cytotoxicity assay. |
| | MonoMethylauristatin F Preparation Products And Raw materials |
| Raw materials | L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-L-valyl-L-valyl-(3R,4S,5S)-3-methoxy-5-methyl-4-(methylamino)heptanoyl-(αR,βR,2S)-β-methoxy-α-methyl-2-pyrrolidinepropanoyl--->L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-L-valyl-L-valyl-(3R,4S,5S)-3-methoxy-5-methyl-4-(methylamino)heptanoyl-(αR,βR,2S)-β-methoxy-α-methyl-2-pyrrolidinepropanoyl-, methyl ester |
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