CAS 474645-27-7|Monomethyl auristatin E

Introduction：Basic information about CAS 474645-27-7|Monomethyl auristatin E, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Monomethyl auristatin E BiologicalActivity
3. Chemical & Physical Properties
4. Synonyms

Common Name	Monomethyl auristatin E
CAS Number	474645-27-7	Molecular Weight	717.979
Density	1.1±0.1 g/cm3	Boiling Point	873.5±65.0 °C at 760 mmHg
Molecular Formula	C₃₉H₆₇N₅O₇	Melting Point	/
MSDS	/	Flash Point	482.1±34.3 °C

Names

Name	[3H]-Vedotin
Synonym	More Synonyms

Monomethyl auristatin E BiologicalActivity

Description	Monomethyl auristatin E (MMAE) is a synthetic derivative of dolastatin 10 and functions as a potent mitotic inhibitor by inhibiting tubulin polymerization. MMAE is widely used as a cytotoxic component of antibody-drug conjugates (ADCs) to treat several different cancer types.
Related Catalog	Signaling Pathways >>Antibody-drug Conjugate >>ADC CytotoxinSignaling Pathways >>Cell Cycle/DNA Damage >>Microtubule/TubulinSignaling Pathways >>Cytoskeleton >>Microtubule/TubulinResearch Areas >>Cancer
Target	Microtubule[1]
In Vitro	Monomethyl auristatin E (MMAE) is efficiently released from SGN-35 within CD30+ cancer cells and, due to its membrane permeability, is able to exert cytotoxic activity on bystander cells[1]. MMAE sensitizes colorectal and pancreatic cancer cells to IR in a schedule and dose dependent manner correlating with mitotic arrest. Radiosensitization is evidenced by decreased clonogenic survival and increased DNA double strand breaks in irradiated cells[2].
In Vivo	Monomethyl auristatin E (MMAE) in combination with IR results in tumor growth delay, tumor-targeted ACPP-cRGD-MMAE with IR produces a more robust and significantly prolongs tumor regression in xenograft models[2].
Cell Assay	Monomethyl auristatin E (MMAE, 5 nM) and ionizing radiation (IR) treated cells are harvested and lysed in RIPA buffer with protease and phosphatase inhibitors. Thirty μg of lysate undergo electrophoresis using 4-12% Bis-Tris gels, transferred to PVDF membranes and incubated with indicated primary antibodies. Blots are developed by ECL.
Animal Admin	Mice[2] 6-8 week old female athymic nu/nu mice are injected subcutaneously into thighs with 5×106 HCT-116 or PANC-1 cells in a 1:1 Matrigel and PBS solution. Mice are treated with IR or intravenous (IV) injection of ACPP-cRGD-MMAE (6 nmoles/day, 18 nmoles total, i.v.), tumor tissue is harvested, formalin fixed and paraffin embedded followed by staining with indicated antibodies. The primary antibody is used at a 1:250 dilution and is visualized using DAB as a chromagen with the UltraMap system.
References	[1]. Okeley, et al. Intracellular Activation of SGN-35, a Potent Anti-CD30 Antibody-Drug Conjugate. Clinical Cancer Research (2010), 16(3), 888-897. [2]. Lisa Buckel, et al. Tumor radiosensitization by monomethyl auristatin E: mechanism of action and targeted delivery. Cancer Res. 2015 Apr 1;75(7):1376-87.

Chemical & Physical Properties

Density	1.1±0.1 g/cm3
Boiling Point	873.5±65.0 °C at 760 mmHg
Molecular Formula	C₃₉H₆₇N₅O₇
Molecular Weight	717.979
Flash Point	482.1±34.3 °C
Exact Mass	717.504028
PSA	149.54000
LogP	4.13
Vapour Pressure	0.0±0.3 mmHg at 25°C
Index of Refraction	1.519
InChIKey	DASWEROEPLKSEI-UIJRFTGLSA-N
SMILES	CCC(C)C(C(CC(=O)N1CCCC1C(OC)C(C)C(=O)NC(C)C(O)c1ccccc1)OC)N(C)C(=O)C(NC(=O)C(NC)C(C)C)C(C)C

Synonyms

MMAE

Monomethyl auristatin E

Monomethylauristatin E

UNII-V7I58RC5EJ

monomethylauristatinE

N-Methyl-L-valyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(1S,2R)-1-hydroxy-1-phenyl-2-propanyl]amino}-1-methoxy-2-methyl-3-oxopropyl]-1-pyrrolidinyl}-3-methoxy-5-methyl-1-oxo-4-heptanyl]-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-

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