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: [C@H]([C@H](C(N[C@@H]([C@@H](O)C1=CC=CC=C1)C)=O)C)(OC)[C@]2(N(C(C[C@H]([C@@H](N(C([C@@H](NC([C@H](C(C)C)NC)=O)[C@H](C)C)=O)C)[C@H](CC)C)OC)=O)CCC2)[H]

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-

MonoMethyl auristatin E

CAS: 474645-27-7

Formula: C₃₉H₆₇N₅O₇

Purity: 97%

Color and Shape: Solid

Molecular weight: 717.9786

Ref: IN-DA00359V

[3H]-Vedotin

CAS: 474645-27-7

[3H]-Vedotin

Purity: 98%

Molecular weight: 717.99g/mol

Ref: 54-OR1025620

Monomethyl auristatin E

CAS: 474645-27-7

Monomethyl auristatin E

Purity: ≥98%

Molecular weight: 717.98g/mol

Ref: 54-BUP11108

Monomethylauristatin E

CAS: 474645-27-7

Formula: C₃₉H₆₇N₅O₇

Color and Shape: Off-White Solid

Molecular weight: 717.99

Ref: 4Z-PA-329001

Monomethyl auristatin E

CAS: 474645-27-7

Monomethyl auristatin E (MMAE) (MMAE), an antimitotic agent, inhibits cell division by blocking the polymerization of tubulin and also has inhibition of

Formula: C₃₉H₆₇N₅O₇

Purity: 98.47% - 99.9%

Color and Shape: Solid

Molecular weight: 717.98

Ref: TM-T6897

MMAE

Controlled Product

CAS: 474645-27-7

Applications MMAE is an effective and synthetic cytotoxic analog of Dolastatin 10 which is a potent antimitotic polypeptide isolated from a marine animal.
References Bai R. et al.: J. biol. Chem., 265, 17141 (1990); Giddens, A. et al.: Bioorg. Med. Chem., 24, 6075 (2016);

Formula: C₃₉H₆₇N₅O₇

Color and Shape: Neat

Molecular weight: 717.98

Ref: TR-M425410

MMAE

CAS: 474645-27-7

Formula: C₃₉H₆₇N₅O₇

Ref: TR-TRC-M425410

Monomethyl auristatin E

CAS: 474645-27-7

Synthetic analog of dolastatin 10; cytotoxic; inhibits tubulin polymerization

Formula: C₃₉H₆₇N₅O₇

Purity: Min. 98 Area-%

Color and Shape: White Off-White Powder

Molecular weight: 717.98 g/mol

Ref: 3D-FM63498

Monomethyl auristatin E

CAS: 474645-27-7

Purity: 98%

Molecular weight: 717.99

Ref: 10-F786682