MMAE is a synthetic antineoplastic agent. Because of its toxicity, it cannot be used as a drug itself; instead, it is linked to a monoclonal antibody (MAB) which directs it to the cancer cells. Monomethyl auristatin E or MMAE is 100-1000 times more potent than doxorubicin. It is a very potent antimitotic agent that inhibits cell division by blocking the polymerization of tubulin.
MMAE is an effective and synthetic cytotoxic analog of Dolastatin 10 which is a potent antimitotic polypeptide isolated from a marine animal.
Dolastatin 10 is a natural antimitotic and antineoplastic agent that binds to tubulin and inhibits tubulin polymerization. Monomethyl Auristatin E (MMAE) is a synthetic analog of dolastatin 10 that similarly inhibits tubulin polymerization and exhibits potent cytotoxicity. It is commonly conjugated with monoclonal antibodies directed at antigens specific to cancer cells for tumor-directed cytotoxicity. MMAE is typically coupled to the antibody via a protease-cleavable linker, allowing separation of the drug from the antibody following intracellular localization.[Cayman Chemical]
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Product Name: | MonoMethyl auristatin E |
Synonyms: | MonoMethyl auristatin E(MMAE, vedotin);HM-297C-22;MonoMethyl auristatin E;MMAE;Vedotin;N-Methyl-L-valyl-N-[(1S,2R)-4-[(2S)-2-[(1R,2R)-3-[[(1R,2S)-2-hydroxy-1-methyl-2-phenylethyl]amino]-1-methoxy-2-methyl-3-oxopropyl]-1-pyrrolidinyl]-2-methoxy-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl-L-valinamide Monomethyl;Monomethyl auristatin E, >=98%;(S)-N-((3R,4S,5S)-1-((S)-2-((1R,2R)-3-(((1R,2R)-1-Hydroxy-1-phenylpropan-2-yl)amino)-1-methoxy-2-methyl-3-oxopropyl)pyrrolidin-1-yl)-3-methoxy-5-methyl-1-oxohe |
CAS: | 474645-27-7 |
MF: | C39H67N5O7 |
MW: | 717.98 |
EINECS: | |
Product Categories: | intermediates;Pharmaceutical; |
Mol File: | 474645-27-7.mol |
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MonoMethyl auristatin E Chemical Properties |
Melting point | >90°C (dec.) |
Boiling point | 873.5±65.0 °C(Predicted) |
density | 1.088±0.06 g/cm3(Predicted) |
storage temp. | -20°C Freezer |
solubility | DMSO (Slightly), Methanol (Slightly, Sonicated) |
pka | 13.66±0.20(Predicted) |
form | Solid |
color | White to Off-White |
InChIKey | RJACXSRFJLSJEZ-UIJRFTGLSA-N |
SMILES | C(NC(=O)[C@H](C(C)C)NC)(=O)[C@H](C(C)C)N([C@@H]([C@@H](C)CC)[C@H](OC)CC(N1CCC[C@H]1[C@H](OC)[C@@H](C)C(N[C@H](C)[C@@H](O)C1=CC=CC=C1)=O)=O)C |
CAS DataBase Reference | 474645-27-7 |
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