Mc-MMAE - CAS 863971-24-8

Mc-MMAE - CAS 863971-24-8 Catalog number: BADC-00025

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Mc-MMAE is a protective group conjugated MMAE, MMAE inhibits tubulin polymerization so that it inhibits cell division.

Category
ADCs Cytotoxin with Linkers
Product Name
Mc-MMAE
CAS
863971-24-8
Catalog Number
BADC-00025
Molecular Formula
C49H78N6O10
Molecular Weight
911.18
Purity
≥98%
Mc-MMAE

Ordering Information

Catalog Number Size Price Quantity
BADC-00025 1 mg $519 Inquiry
Description
Mc-MMAE is a protective group conjugated MMAE, MMAE inhibits tubulin polymerization so that it inhibits cell division.
Synonyms
Maleimidocaproyl-monomethylauristatin E; N-[6-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-N-methyl-L-valyl-N-[(3R,4S,5S)-1-{(2S)-2-[(1R,2R)-3-{[(1S,2R)-1-hydroxy-1-phenyl-2-propanyl]amino}-1-methoxy-2-methyl-3-oxopropyl]-1-pyrrolidinyl}- 3-methoxy-5-methyl-1-oxo-4-heptanyl]-N-methyl-L-valinamide;
IUPAC Name
6-(2,5-dioxopyrrol-1-yl)-N-[(2S)-1-[[(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]amino]-3-methyl-1-oxobutan-2-yl]-N-methylhexanamide
Canonical SMILES
CC[C@]([C@@](N(C([C@](/N=C(O)/[C@](N(C(CCCCCN1C(C=CC1=O)=O)=O)C)([H])C(C)C)([H])C(C)C)=O)C)([H])[C@@](OC)([H])CC(N2CCC[C@@]2([H])[C@@](OC)([H])[C@@](/C(O)=N/[C@]([C@](O)([H])C3=CC=CC=C3)([H])C)([H])C)=O)([H])C
InChI
InChI=1S/C49H78N6O10/c1-13-32(6)44(37(64-11)29-41(59)54-28-20-23-36(54)46(65-12)33(7)47(61)50-34(8)45(60)35-21-16-14-17-22-35)53(10)49(63)42(30(2)3)51-48(62)43(31(4)5)52(9)38(56)24-18-15-19-27-55-39(57)25-26-40(55)58/h14,16-17,21-22,25-26,30-34,36-37,42-46,60H,13,15,18-20,23-24,27-29H2,1-12H3,(H,50,61)(H,51,62)/t32-,33+,34+,36-,37+,42-,43-,44-,45+,46+/m0/s1
InChIKey
UGJOTJHSQWBROP-AXJCKIDNSA-N
LogP
4.91180
PSA
195.20000
Appearance
Soild powder
Shelf Life
≥360 days if stored properly
Shipping
Room temperature

Mc-MMAE (Monomethyl Auristatin E) is a potent cytotoxic peptide-conjugate used extensively in the development of antibody-drug conjugates (ADCs) for targeted cancer therapies. MMAE, a potent microtubule-disrupting agent, is linked to a peptide carrier to improve its solubility and stability. Mc-MMAE is utilized to specifically deliver MMAE to cancer cells, minimizing off-target toxicity while maximizing therapeutic efficacy. Its targeted delivery system has shown great promise in treating a variety of cancers, including lymphoma, breast cancer, and ovarian cancer.

One of the primary applications of Mc-MMAE is in the design of antibody-drug conjugates (ADCs). ADCs are a class of therapeutic agents that combine the specificity of monoclonal antibodies with the potency of cytotoxic drugs, such as MMAE. Mc-MMAE serves as an efficient linker in these ADC formulations, ensuring that the cytotoxic MMAE payload is delivered directly to tumor cells, where it disrupts microtubules and inhibits cell division. This approach significantly improves the precision of cancer treatment, offering a more targeted and effective therapy with reduced side effects compared to traditional chemotherapy.

Another key application of Mc-MMAE is in the optimization of drug delivery systems. The peptide-based linker between MMAE and Mc-MMAE not only enhances the stability of the cytotoxic payload but also enables it to bypass normal tissues and accumulate more selectively at tumor sites. This selective targeting minimizes the systemic toxicity typically associated with MMAE and other cytotoxic drugs. Researchers continue to optimize Mc-MMAE's structure to improve its pharmacokinetic properties, thereby enhancing its potential for use in clinical settings for cancer therapies.

Mc-MMAE is also utilized in the study of targeted therapy and cancer cell behavior. By using Mc-MMAE conjugates in vitro and in vivo, researchers can investigate the mechanisms of action of microtubule-targeting drugs and gain insights into how cancer cells evade treatment. This application has led to a deeper understanding of drug resistance mechanisms and has paved the way for the development of second-generation ADCs with improved efficacy and reduced resistance. The conjugation of MMAE to peptide carriers like Mc-MMAE helps fine-tune the drug’s delivery and its ability to overcome these resistance mechanisms.

In addition to its use in cancer therapies, Mc-MMAE also holds potential in the development of treatments for other diseases involving abnormal cell proliferation, such as autoimmune disorders. By targeting the underlying cellular mechanisms responsible for disease progression, Mc-MMAE-based therapies could provide a more precise treatment option for conditions where controlling cell division is crucial. The ability to modulate the activity of microtubules and cell cycle progression opens up potential applications beyond oncology, making Mc-MMAE a versatile tool in therapeutic research.

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

Historical Records: Fmoc-VC-PAB-MMAE
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