MMAE - CAS 474645-27-7
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MMAE - CAS 474645-27-7 Catalog number: BADC-00324

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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.

Category
ADCs Cytotoxin
Product Name
MMAE
CAS
474645-27-7
Catalog Number
BADC-00324
Molecular Formula
C39H67N5O7
Molecular Weight
717.98
Target
Microtubule/Tubulin
MMAE

Ordering Information

Catalog Number Size Price Quantity
BADC-00324 25 mg $298
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Description
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.
Synonyms
MMAE; Vedotin; Monomethyl auristatin E; Monomethylauristatin E; N-methyl-L-valyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino}-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl}-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide
IUPAC Name
(2S)-N-[(2S)-1-[[(3R,4S,5S)-1-[(2S)-2-[(1R,2R)-3-[[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino]-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl]-3-methoxy-5-methyl-1-oxoheptan-4-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-3-methyl-2-(methylamino)butanamide
Canonical SMILES
CC(C)C(C(CC(=O)N1CCCC1C(C(C)C(=O)NC(C)C(C2=CC=CC=C2)O)OC)OC)N(C)C(=O)C(C(C)C)NC(=O)C(C(C)C)NC
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
InChIKey
DASWEROEPLKSEI-UIJRFTGLSA-N
Density
1.088±0.06 g/cm3 (Predicted)
Solubility
Soluble in DMSO (Slightly), Methanol (Slightly, Sonicated); Insoluble in Water
Melting Point
>90°C (dec.)
Flash Point
482.1±34.3 °C
Index Of Refraction
1.519
LogP
4.13
PSA
149.54000
Vapor Pressure
0.0±0.3 mmHg at 25°C
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. 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.
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.
Clinical Trial Information
NCT NumberCondition Or DiseasePhaseStart DateSponsorStatus
NCT05113459Gastric CancerPhase 22021-11-09Guoxin LiNot yet recruiting
NCT03187210LymphomaPhase 1, Phase 22021-08-05University Hospital Inselspital, BerneRecruiting
NCT04679012Richter SyndromePhase 22021-09-22Weill Medical College of Cornell UniversityNot yet recruiting
NCT05006664Lymphoma, T-Cell, PeripheralPhase 22021-09-01Czech Lymphoma Study GroupNot yet recruiting
NCT02227433Hodgkin LymphomaPhase 22020-12-22Fondazione Italiana Linfomi ONLUSCompleted
Application
ADCs Cytotoxin
Appearance
White to Off-white Solid
Purity
≥98.0% by HPLC
Shipping
Ice packs
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Pictograms
Irritant; Health Hazard
Signal Word
Warning
Boiling Point
873.5±65.0 °C at 760 mmHg
1.An anti-HER2 antibody conjugated with monomethyl auristatin E is highly effective in HER2-positive human gastric cancer.
Li H1, Yu C2, Jiang J3, Huang C2, Yao X1, Xu Q2, Yu F2, Lou L4, Fang J1,5,6. Cancer Biol Ther. 2016 Apr 2;17(4):346-54. doi: 10.1080/15384047.2016.1139248. Epub 2016 Feb 6.
Antibody-drug conjugate (ADC) is a novel class of therapeutics for cancer target therapy. This study assessed antitumor activity of ADC with an antimitotic agent, monomethyl auristatin E (MMAE) and a humanized monoclonal anti-HER2 antibody, hertuzumab, in gastric cancer. The efficacy of hertuzumab-MC-Val-Cit-PAB-MMAE (hertuzumab-vcMMAE) on human epidermal growth factor receptor 2 (HER2) positive human gastric cancer cells, NCI-N87, was evaluated in vitro and in vivo. The cytotoxicity of hertuzumab was significantly enhanced after conjugation with MMAE. Compared to trastuzumab, hertuzumab had a higher affinity to HER2 and had more potent antibody-dependent cell-mediated cytotoxicity (ADCC) activity in vitro. After conjugation with MMAE, the binding specificity for HER2 was not affected. Furthermore, the internalization of hertuzumab-vcMMAE in HER2 positive gastric cancer cells was verified. Although the conjugation of hertuzumab and MMAE decreased the ADCC effect, the overall cytotoxicity was dramatically increased in HER2 positive gastric cancer cells.
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Historical Records: MMAE
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