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

Ordering Information

Catalog Number	Size	Price	Quantity
BADC-00324	25 mg	$298

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Products Information
Reference Reading

Description

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 Number	Condition Or Disease	Phase	Start Date	Sponsor	Status
NCT05113459	Gastric Cancer	Phase 2	2021-11-09	Guoxin Li	Not yet recruiting
NCT03187210	Lymphoma	Phase 1, Phase 2	2021-08-05	University Hospital Inselspital, Berne	Recruiting
NCT04679012	Richter Syndrome	Phase 2	2021-09-22	Weill Medical College of Cornell University	Not yet recruiting
NCT05006664	Lymphoma, T-Cell, Peripheral	Phase 2	2021-09-01	Czech Lymphoma Study Group	Not yet recruiting
NCT02227433	Hodgkin Lymphoma	Phase 2	2020-12-22	Fondazione Italiana Linfomi ONLUS	Completed

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.