CAS 474645-27-7: Monomethylauristatin E
Description:Monomethylauristatin E (MMAE) is a synthetic antineoplastic agent primarily used in the development of antibody-drug conjugates (ADCs) for targeted cancer therapy. It is a potent microtubule inhibitor derived from the natural product dolastatin 10, which is known for its ability to disrupt the mitotic spindle, thereby inhibiting cell division. MMAE is characterized by its ability to induce apoptosis in cancer cells, making it effective against various malignancies. The compound features a unique structure that includes a modified peptide backbone, which enhances its stability and solubility compared to its parent compound. Its mechanism of action involves binding to tubulin, leading to cell cycle arrest and ultimately cell death. Due to its specificity when conjugated to antibodies, MMAE minimizes systemic toxicity while maximizing therapeutic efficacy. The compound is under investigation in clinical settings, showcasing its potential in treating hematological malignancies and solid tumors. As with many cytotoxic agents, careful handling and consideration of safety protocols are essential when working with MMAE in laboratory and clinical environments.
Formula:C39H67N5O7
InChI:InChI=1S/C39H67N5O7/c1-13-25(6)34(43(10)39(49)33(24(4)5)42-38(48)32(40-9)23(2)3)30(50-11)22-31(45)44-21-17-20-29(44)36(51-12)26(7)37(47)41-27(8)35(46)28-18-15-14-16-19-28/h14-16,18-19,23-27,29-30,32-36,40,46H,13,17,20-22H2,1-12H3,(H,41,47)(H,42,48)/t25-,26+,27+,29-,30+,32-,33-,34-,35+,36+/m0/s1
InChI key:InChIKey=DASWEROEPLKSEI-UIJRFTGLSA-N
SMILES:O=C(NC(C(=O)N(C)C(C(OC)CC(=O)N1CCCC1C(OC)C(C(=O)NC(C)C(O)C=2C=CC=CC2)C)C(C)CC)C(C)C)C(NC)C(C)C
- Synonyms:
- <span class="text-smallcaps">L</smallcap>-Valinamide, N-methyl-<smallcap>L</span>-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-
- MMAE toxin
- Mmae
- Monomethylauristatin E
- Monomethylauristatin norephedrine
- N-Methyl-<span class="text-smallcaps">L</smallcap>-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-<smallcap>L</span>-valinamide
- Toxin MMAE
- 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
- L-Valinamide, 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-
