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    Monomethyl auristatin E (MMAE)
    Monomethyl auristatin E (MMAE)

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V1887
    CAS #: 474645-27-7 Purity ≥98%

    Description: Monomethyl auristatin E (also known as MMAE; SGD-1010), a dolastatin 10 derivative, is a novel, synthetic and potent antimitotic/antitubulin agent which blocks the polymerization of tubulin, due to its high toxicity, it cannot be used as a drug itself; instead, it is linked to a monoclonal antibody (MAB) which directs it to the cancer cells. In the marketed drug Brentuximab vedotin, the name vedotin refers to MMAE plus its linking structure to the antibody (Brentuximab). MMAE is a potent antimitotic drug derived from peptides occurring in marine shell-less mollusc Dolabella auricularia called dolastatins which show potent activity in preclinical studies, both in vitro and in vivo, against a range of lymphomas, leukemia and solid tumors. MMAE show potency of up to 200 times that of vinblastine, another antimitotic drug used for Hodgkin lymphoma as well as other types of cancer. 

    References: Blood. 2003 Aug 15;102(4):1458-65; Blood. 2009 Sep 24;114(13):2721-9. 

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    Molecular Weight (MW)717.98 
    CAS No.474645-27-7 
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 100 mg/mL (139.3 mM) 
    Water: <1 mg/mL
    Ethanol: 100 mg/mL (139.3 mM) 
    Other info
    Chemical Name: (S)-2-(((3R,4S,5S)-1-((S)-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)(methyl)amino)-3-methyl-N-((S)-3-methyl-2-(methylamino)butanoyl)butanamide.

    SMILES Code: CC(C)[[email protected]@H](C(NC([[email protected]](C(C)C)NC)=O)=O)N([[email protected]@H]([[email protected]@H](C)CC)[[email protected]](OC)CC(N1[[email protected]]([[email protected]](OC)[[email protected]@H](C)C(N[[email protected]](C)[[email protected]@H](O)C2=CC=CC=C2)=O)CCC1)=O)C 

    Exact Mass: 717.50405 

    SynonymsSGD1010; SGD 1010; SGD-1010; MMAE; Vedotin; Monomethyl auristatin E. 

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    In Vitro

    In vitro activity: When coupled to cAC10, MMAE shows selective cytotoxicity in CD30+ cells, and induces G2/M-phase growth arrest and cell death through the induction of apoptosis. [1] When coupled to anti-CD79b antibody, anti–CD79b-vcMMAE has very potent and broad activity across a large panel of NHL cell lines in vitro. [2] When coupled to anti-HER2 antibody, hertuzumab-vc-MMAE can also be effectively internalized and potently kill HER2 over-expressing tumor cells.

    Cell Assay: Cytotoxicity is measured using Alamar Blue dye reduction assay according to the manufacturer's directions. Briefly, a 40% solution (wt/vol) of Alamar Blue is freshly prepared in complete media just before cultures are added. Ninety-two hours after drug exposure, Alamar Blue solution is added to cells to constitute 10% culture volume. Cells are incubated for 4 hours, and dye reduction is measured on a Fusion HT fluorescent plate reader (Packard Instruments, Meriden, CT). Cell lines used: CD30+ Karpas 299 cells

    In VivoThe Karpas 299 ALCL model, cAC10-vcMMAE (1 mg/kg, i.v.) induces complete, durable tumor regression, while free MMAE (0.36 mg/kg) doesn’t produce detectable antitumor activity. In mouse xenograft models of NHL, anti–CD79b-vcMMAE (7 mg/kg, p.o.) strikingly results in sustained complete tumor remission. 
    Animal modelIn vivo therapy tests were undertaken in athymic mice with subcutaneous L2987 human lung adenocarcinoma xenografts. MMAE conjugates were administered at 3 mg mAb component/kg/dose. All of the tested MMAE conjugates were highly efficacious, leading to long-term regressions of established tumors, whereas the nonbinding control conjugates had no effect on tumor growth. In addition, there were no apparent toxicities associated with conjugate treatment  
    Formulation & Dosage6-8 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.
    ReferencesBlood. 2003 Aug 15;102(4):1458-65; Blood. 2009 Sep 24;114(13):2721-9; Nat Biotechnol. 2003 Jul;21(7):778-84.  

    These protocols are for reference only. InvivoChem does not independently validate these methods.

    Monomethyl auristatin E (MMAE) MMAE has increased potency compared to paclitaxel in tumor cells.  2015 Apr 1;75(7):1376-1387. Monomethyl auristatin E (MMAE) MMAE increases IR induced DNA double strand breaks in a schedule and dose dependent manner.  2015 Apr 1;75(7):1376-1387. Monomethyl auristatin E (MMAE) MMAE decreases clonogenic survival of irradiated tumor cells.  2015 Apr 1;75(7):1376-1387.
     Monomethyl auristatin E (MMAE) MMAE increases DNA damage response in irradiated tumor cells.  2015 Apr 1;75(7):1376-1387. Monomethyl auristatin E (MMAE) ACPP-cRGD-MMAE in combination with IR significantly reduces tumor growth.  2015 Apr 1;75(7):1376-1387. Monomethyl auristatin E (MMAE) Activatable cell penetrating peptides are cleaved in irradiated tumor microenvironments. A) Orthotopic pancreatic adenocarcinoma PDX were harvested and zymography gels used to assess gelatinase activity, lysates. For each PDX, lysates were run in duplicate (lanes A and B). 2015 Apr 1;75(7):1376-1387.


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