Mal-Phe-C4-VC-PAB-MMAE - CAS 2259318-51-7

Mal-Phe-C4-VC-PAB-MMAE - CAS 2259318-51-7 Catalog number: BADC-00866

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Mal-Phe-C4-VC-PAB-MMAE is made by MMAE conjugated to Mal-Phe-C4-VC-PAB linker. Monomethyl auristatin E (MMAE), a potent tubulin inhibitor, is a toxin payload in antibody drug conjugate.

Category
ADCs Cytotoxin
Product Name
Mal-Phe-C4-VC-PAB-MMAE
CAS
2259318-51-7
Catalog Number
BADC-00866
Molecular Formula
C72H105N11O15
Molecular Weight
1364.67
Purity
>98.0%

Ordering Information

Catalog Number Size Price Quantity
BADC-00866 -- $-- Inquiry
Description
Mal-Phe-C4-VC-PAB-MMAE is made by MMAE conjugated to Mal-Phe-C4-VC-PAB linker. Monomethyl auristatin E (MMAE), a potent tubulin inhibitor, is a toxin payload in antibody drug conjugate.
IUPAC Name
[4-[[(2S)-5-(carbamoylamino)-2-[[(2S)-2-[4-[4-(2,5-dioxopyrrol-1-yl)phenyl]butanoylamino]-3-methylbutanoyl]amino]pentanoyl]amino]phenyl]methyl 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-methylcarbamate
Canonical SMILES
CCC(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)N(C)C(=O)OCC3=CC=C(C=C3)NC(=O)C(CCCNC(=O)N)NC(=O)C(C(C)C)NC(=O)CCCC4=CC=C(C=C4)N5C(=O)C=CC5=O
InChI
InChI=1S/C72H105N11O15/c1-15-45(8)63(55(96-13)40-59(87)82-39-21-26-54(82)65(97-14)46(9)66(89)75-47(10)64(88)50-23-17-16-18-24-50)80(11)70(93)61(43(4)5)79-69(92)62(44(6)7)81(12)72(95)98-41-49-28-32-51(33-29-49)76-67(90)53(25-20-38-74-71(73)94)77-68(91)60(42(2)3)78-56(84)27-19-22-48-30-34-52(35-31-48)83-57(85)36-37-58(83)86/h16-18,23-24,28-37,42-47,53-55,60-65,88H,15,19-22,25-27,38-41H2,1-14H3,(H,75,89)(H,76,90)(H,77,91)(H,78,84)(H,79,92)(H3,73,74,94)/t45-,46+,47+,53-,54-,55+,60-,61-,62-,63-,64+,65+/m0/s1
Solubility
10 mm in DMSO
Appearance
Solid
Shelf Life
0-4°C for short term (days to weeks), or -20°C for long term (months).
Shipping
Room temperature
Storage
Store at -20 °C, keep in dry and avoid sunlight.
Form
Solid

Mal-Phe-C4-VC-PAB-MMAE is a highly versatile compound used primarily in the development of targeted cancer therapies, especially in antibody-drug conjugates (ADCs). The maleimide (Mal) group allows for specific and efficient conjugation to thiol-containing molecules such as antibodies or peptides, ensuring precise targeting of tumor cells. The VC (valine-citrulline) linker is designed to be cleaved by enzymes present in the tumor microenvironment, releasing the cytotoxic drug MMAE (monomethyl auristatin E) directly at the target site. This targeted release of MMAE enhances the therapeutic effect while minimizing systemic toxicity, making it a key component of ADC-based therapies.

A major application of Mal-Phe-C4-VC-PAB-MMAE is in the development of ADCs for cancer treatment. In ADCs, the compound links the potent cytotoxic agent MMAE to a targeting antibody or peptide. The cleavable VC linker ensures that the drug is only released within the tumor cells, where it can be activated by tumor-specific enzymes. This selective drug release improves the precision of the therapy, significantly reducing off-target effects and enhancing the therapeutic efficacy of the treatment. The PAB (p-aminobenzyl) group serves as a spacer, improving the stability and solubility of the conjugate, while the overall design ensures the efficient delivery of the drug to the tumor site.

Mal-Phe-C4-VC-PAB-MMAE is also utilized in the creation of peptide-drug conjugates (PDCs), where peptides serve as targeting agents to direct MMAE to specific tissues. This application benefits from the same cleavable VC linker, ensuring the selective release of MMAE in the tumor microenvironment. By conjugating MMAE with targeting peptides, the compound enhances the specificity and efficiency of cancer therapies. The incorporation of PAB improves the solubility of the conjugate, allowing it to circulate in the bloodstream for longer periods without rapid clearance, thereby increasing the exposure time of the drug at the target site.

Beyond cancer treatment, Mal-Phe-C4-VC-PAB-MMAE can be used in molecular imaging and diagnostic applications. By attaching imaging agents, such as fluorescent dyes or radiolabels, to antibodies or peptides, this compound enables the precise detection of disease biomarkers. The cleavable VC linker ensures that the imaging agents are released only in the targeted tissues, improving the sensitivity and accuracy of the imaging process. This makes Mal-Phe-C4-VC-PAB-MMAE a valuable tool in the development of diagnostic technologies for cancer and other diseases, facilitating early detection and more accurate monitoring of treatment responses.

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: Mal-Phe-C4-VC-PAB-MMAE
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