MMAD

Tubulin inhibitor,highly potent CAS# 203849-91-6

MMAD

Catalog No. BCC1774----Order now to get a substantial discount!

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Quality Control of MMAD

Number of papers citing our products

Chemical structure

MMAD

3D structure

Chemical Properties of MMAD

Cas No. 203849-91-6 SDF Download SDF
PubChem ID 10723894 Appearance Powder
Formula C41H66N6O6S M.Wt 771.06
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Demethyldolastatin 10; Monomethylauristatin D; Monomethyl Dolastatin 10
Solubility DMSO : 24.5 mg/mL (31.77 mM; Need ultrasonic and warming)
Chemical Name (2S)-N-[(2S)-1-[[(3R,4S,5S)-3-methoxy-1-[(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-[[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino]propyl]pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-methylamino]-3-methyl-1-oxobutan-2-yl]-3-methyl-2-(methylamino)butanamide
SMILES CCC(C)C(C(CC(=O)N1CCCC1C(C(C)C(=O)NC(CC2=CC=CC=C2)C3=NC=CS3)OC)OC)N(C)C(=O)C(C(C)C)NC(=O)C(C(C)C)NC
Standard InChIKey BLUGYPPOFIHFJS-UUFHNPECSA-N
Standard InChI InChI=1S/C41H66N6O6S/c1-12-27(6)36(46(9)41(51)35(26(4)5)45-39(50)34(42-8)25(2)3)32(52-10)24-33(48)47-21-16-19-31(47)37(53-11)28(7)38(49)44-30(40-43-20-22-54-40)23-29-17-14-13-15-18-29/h13-15,17-18,20,22,25-28,30-32,34-37,42H,12,16,19,21,23-24H2,1-11H3,(H,44,49)(H,45,50)/t27-,28+,30-,31-,32+,34-,35-,36-,37+/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of MMAD

DescriptionMonomethyl auristatin D (MMAD) is a potent inhibitor of tubulin.
TargetstubulinADCs toxin    

Protocol

Cell experiment:[1]

Preparation method

The solubility of this compound in DMSO is >10 mM. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while.Stock solution can be stored below -20°C for several months.

Applications

MMAD is a highly potent inhibitor of tubulin [1]. MMAD is one of the auristatins, which are used as the drugs of antibody drug conjugates (ADCs). In ADCs, the therapeutic compounds and the high selectivity of antibodies are combined by the linkers. By taking advantage of antigen-selectivity of MAbs, it can deliver these cytotoxic drugs to antigen-expressing tumor cells, thus increasing both the efficacy and safety of therapy. As a payload of ADCs, MMAD is used to target the tubulin of the tumor cells. It can interfere with tubulin polymerization and induce rapid cell death at low picomolar concentrations [1]. Additionally, MMAD is reported to be used in the production of site-specific antibody drug conjugates (NDCs). In the NDCs, MMAD is combined with anti-5T4 antibody or anti-Her2 antibody. It is shown that the NDCs demonstrate better efficacy and pharmacokinetics [2].

References:

[1] Puja Sapra, Andrea T Hooper, Christopher J, O’Donnell & Hans-Peter Gerber. Investigational antibody drug conjugates for solid tumors. Expert Opin. Investig. Drugs. 2011, 20(8):1131-1149.

[2] Feng Tiana, Yingchun Lu, Anthony Manibusan, Aaron Sellers et al. A general approach to site-specific antibody drug conjugates. PNAS. 2014, February, 111(5): 1766-1771.

MMAD Dilution Calculator

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MMAD Molarity Calculator

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Preparing Stock Solutions of MMAD

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.2969 mL 6.4846 mL 12.9692 mL 25.9383 mL 32.4229 mL
5 mM 0.2594 mL 1.2969 mL 2.5938 mL 5.1877 mL 6.4846 mL
10 mM 0.1297 mL 0.6485 mL 1.2969 mL 2.5938 mL 3.2423 mL
50 mM 0.0259 mL 0.1297 mL 0.2594 mL 0.5188 mL 0.6485 mL
100 mM 0.013 mL 0.0648 mL 0.1297 mL 0.2594 mL 0.3242 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on MMAD

MMAD is a highly potent inhibitor of tubulin [1].

MMAD is one of the auristatins, which are used as the drugs of antibody drug conjugates (ADCs). In ADCs, the therapeutic compounds and the high selectivity of antibodies are combined by the linkers. By taking advantage of antigen-selectivity of MAbs, it can deliver these cytotoxic drugs to antigen-expressing tumor cells, thus increasing both the efficacy and safety of therapy. As a payload of ADCs, MMAD is used to target the tubulin of the tumor cells. It can interfere with tubulin polymerization and induce rapid cell death at low picomolar concentrations [1].

Additionally, MMAD is reported to be used in the production of site-specific antibody drug conjugates (NDCs). In the NDCs, MMAD is combined with anti-5T4 antibody or anti-Her2 antibody. It is shown that the NDCs demonstrate better efficacy and pharmacokinetics [2].

References:
[1] Puja Sapra, Andrea T Hooper, Christopher J, O’Donnell & Hans-Peter Gerber. Investigational antibody drug conjugates for solid tumors. Expert Opin. Investig. Drugs. 2011, 20(8):1131-1149.
[2] Feng Tiana, Yingchun Lu, Anthony Manibusan, Aaron Sellers et al. A general approach to site-specific antibody drug conjugates. PNAS. 2014, February, 111(5): 1766-1771.

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References on MMAD

MMAD: microarray microdissection with analysis of differences is a computational tool for deconvoluting cell type-specific contributions from tissue samples.[Pubmed:24085566]

Bioinformatics. 2014 Mar 1;30(5):682-9.

BACKGROUND: One of the significant obstacles in the development of clinically relevant microarray-derived biomarkers and classifiers is tissue heterogeneity. Physical cell separation techniques, such as cell sorting and laser-capture microdissection, can enrich samples for cell types of interest, but are costly, labor intensive and can limit investigation of important interactions between different cell types. RESULTS: We developed a new computational approach, called microarray microdissection with analysis of differences (MMAD), which performs microdissection in silico. Notably, MMAD (i) allows for simultaneous estimation of cell fractions and gene expression profiles of contributing cell types, (ii) adjusts for microarray normalization bias, (iii) uses the corrected Akaike information criterion during model optimization to minimize overfitting and (iv) provides mechanisms for comparing gene expression and cell fractions between samples in different classes. Computational microdissection of simulated and experimental tissue mixture datasets showed tight correlations between predicted and measured gene expression of pure tissues as well as tight correlations between reported and estimated cell fraction for each of the individual cell types. In simulation studies, MMAD showed superior ability to detect differentially expressed genes in mixed tissue samples when compared with standard metrics, including both significance analysis of microarrays and cell type-specific significance analysis of microarrays. CONCLUSIONS: We have developed a new computational tool called MMAD, which is capable of performing robust tissue microdissection in silico, and which can improve the detection of differentially expressed genes. MMAD software as implemented in MATLAB is publically available for download at http://sourceforge.net/projects/MMAD/.

Description

MMAD is a potent tubulin inhibitor, is a toxin payload in antibody drug conjugates (ADCs).

Keywords:

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