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Mc-MMAD

  CAS No.: 1401963-15-2   Cat No.: BADC-00026   Purity: >98% 4.5  

Monomethyl auristatin D (MMAD), a potent tubulin inhibitor, is a toxin payload in antibody drug conjugate; Mc-MMAD is a protective group (maleimidocaproyl) -conjugated MMAD.

Mc-MMAD

Structure of 1401963-15-2

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Category
ADC Cytotoxin
Molecular Formula
C51H77N7O9S
Molecular Weight
964.26
Shipping
Room temperature

* For research and manufacturing use only. We do not sell to patients.

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Synonyms
Mc MMAD; McMMAD
IUPAC Name
6-(2,5-dioxopyrrol-1-yl)-N-[(2S)-1-[[(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]amino]-3-methyl-1-oxobutan-2-yl]-N-methylhexanamide
Canonical 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)N(C)C(=O)CCCCCN4C(=O)C=CC4=O
InChI
InChI=1S/C51H77N7O9S/c1-12-34(6)46(56(9)51(65)44(32(2)3)54-49(64)45(33(4)5)55(8)40(59)23-17-14-18-27-58-41(60)24-25-42(58)61)39(66-10)31-43(62)57-28-19-22-38(57)47(67-11)35(7)48(63)53-37(50-52-26-29-68-50)30-36-20-15-13-16-21-36/h13,15-16,20-21,24-26,29,32-35,37-39,44-47H,12,14,17-19,22-23,27-28,30-31H2,1-11H3,(H,53,63)(H,54,64)/t34-,35+,37-,38-,39+,44-,45-,46-,47+/m0/s1
InChIKey
OZUQLKHIIRUJRZ-PGBUMTRMSA-N
Appearance
Solid Power
Shelf Life
≥360 days if stored properly
Shipping
Room temperature

Mc-MMAD, a modified peptide featuring a combination of methionine, methionine sulfoxide, and aspartic acid residues, is widely used in various fields of biochemical and pharmaceutical research. Its unique composition, combining both sulfur-containing amino acids and a carboxyl group, imparts distinct properties that make it highly suitable for applications in peptide synthesis, drug development, and molecular biology. This peptide's chemical reactivity and structural flexibility offer opportunities for a range of applications, particularly in targeting disease mechanisms and optimizing drug delivery.

One of the key applications of Mc-MMAD is in the development of targeted therapies and drug delivery systems. The methionine residue, especially when oxidized to methionine sulfoxide, plays a crucial role in redox-sensitive processes, making Mc-MMAD useful in designing drugs that are activated or degraded under specific oxidative conditions. This property is particularly valuable in the development of therapies that target oxidative stress-related diseases, such as neurodegenerative disorders and cardiovascular diseases. By modulating the redox state of the peptide, researchers can create more effective and controlled drug delivery systems that respond to the unique biochemical environments of diseases.

Mc-MMAD is also employed in the study of protein-protein interactions and enzymatic activity. The presence of aspartic acid in its sequence allows Mc-MMAD to act as a mimic of certain peptide substrates or inhibitors. Researchers use it to study enzyme mechanisms, particularly those involved in redox reactions and oxidative damage repair. Mc-MMAD can be employed in screening assays to identify novel inhibitors or activators of enzymes involved in cellular stress responses, providing potential therapeutic avenues for treating diseases related to protein misfolding or oxidative damage.

Another important application of Mc-MMAD lies in the development of peptide-based materials for biomedical purposes. The sulfur-containing methionine and methionine sulfoxide residues confer the peptide with the ability to form cross-links or interact with metal ions, which can be exploited to create biomaterials with enhanced mechanical or chemical properties. These materials have potential uses in tissue engineering, wound healing, and drug delivery systems, where stability and controlled release of therapeutic agents are essential. Mc-MMAD's ability to form strong, stable bonds makes it a promising candidate for the development of more durable and functional peptide-based biomaterials.

In addition, Mc-MMAD is utilized in the synthesis of peptide conjugates for molecular imaging and diagnostic applications. Its structure can be modified with fluorescent or radioactive tags, making it an ideal candidate for the design of diagnostic probes. These probes can be used in non-invasive imaging techniques, such as PET or MRI, to track the distribution of peptides in the body and monitor disease progression. By attaching Mc-MMAD to targeting molecules, researchers can improve the specificity and sensitivity of diagnostic imaging, offering insights into the localization and behavior of disease markers.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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Historical Records: N-Acetyl-Calicheamicin | BS3 Crosslinker disodium | Azidoethyl-SS-propionic NHS ester | BCN-PEG4-acid | MC-va-PAB-MMAD | Cys-mcMMAD | MC-vc-PAB-MMAD | OSu-Glu-vc-PAB-MMAD | DBCO-PEG4-vc-PAB-MMAD | Vc-MMAD | Mc-MMAD
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