646502-53-6

Basic information

• Product Name: VcMMAE
• Synonyms: VcMMAE;MC-Val-Cit-PAB-MMAE;Maleimidocaproyl-valine-citrulline-p-aminobenzoyloxycarbonyl-monomethyl auristatin E;4-((S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3-methylbutanamido)-5-ureidopentanamido)benzyl((S)-1-(((S)-1-(((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-y;MC-VC-PAB-MMAE,MC-Val-Cit-PAB-MMAE;maleimido-caproyl-val-Cit-PAB-MMAE;VeMMAE;EOS-60990
• CAS NO: 646502-53-6
• Molecular Formula: C68H105N11O15
• Molecular Weight: 1316.626
• Mol File: 646502-53-6.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 1347.6±65.0 °C(Predicted)
• Appearance: /
• Density: 1.196±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in DMSO, DCM, DMF
• PKA: 13.29±0.70(Predicted)
• CAS DataBase Reference: VcMMAE(CAS DataBase Reference)
• NIST Chemistry Reference: VcMMAE(646502-53-6)
• EPA Substance Registry System: VcMMAE(646502-53-6)

Safety Data

• Hazardous Substances Data: 646502-53-6(Hazardous Substances Data)

Usage

Description

VcMMAE, also known as MC-Val-Cit-PAB-MMAE, is a precursor of antibody drug conjugate that contains a thio reactive maleimidocaproyl (MC) group, a protease-sensitive Val-Cit dipeptide, a PABC linker, and a MMAE payload. The MMAE is a synthetic antineoplastic agent that can be attached to a monoclonal antibody (MAB) to direct it towards cancer cells.

Uses

Used in Pharmaceutical Industry:
VcMMAE is used as a precursor for antibody drug conjugates for the development of targeted cancer therapies. The MMAE payload, a synthetic antineoplastic agent, can be attached to a monoclonal antibody (MAB) to selectively target and kill cancer cells while minimizing damage to healthy cells.
Used in Tumor-Targeting Applications:
Vedotin, an ultra-high-affinity small organic ligand of fibroblast activation protein, is used in conjunction with VcMMAE for tumor-targeting applications. This combination allows for the specific delivery of the MMAE payload to cancer cells, enhancing the therapeutic efficacy and reducing side effects associated with traditional chemotherapy.

Upstream product

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• 474645-27-7 [3H]-Vedotin 
• 68858-20-8 Fmoc-Val-OH 
• 372-75-8 Citrulline 
• 159858-21-6 (S)-2-((S)-2-((((9H-fluoren-9-yl)-methoxy)carbonyl)amino)-3-methylbutanamido)-5-ureidopentanoic acid 
• 159858-22-7 (9H-fluorenyl)methyl ((S)-1-(((S)-1-(((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidovalerylamido-2-yl)amino))-3-methylbutyramido-2-yl)-carbamate 
• 159857-79-1 (2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-N-[4-(hydroxymethyl)phenyl]-5-ureidopentanamide 
• 159857-80-4 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-N-((S)-1-(((S)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxo-5-ureidopentan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)hexanamide 
• 60-32-2 6-aminohexanoic acid 
• 55750-53-3 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid 
• 623-04-1 4-aminobenzenemethanol 
• 130878-68-1 2,5-dioxopyrrolidin-1-yl-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valinate 
• 1375415-93-2 tert-butyl (3R,4S,5S)-4-[(2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-N,3-dimethylbutanamido]-3-methoxy-5-methylheptanoate 

Relevant articles and documents

EFFICIENT PREPARATION OF DOLASTATIN AND AURISTATIN ANALOGS THROUGH A COMMON INTERMEDIATE

Methods for making a dolastatin, auristatin or related compounds comprising the steps of providing a universal dolastatin core of Formula (I) reacting the C-terminal carboxylic acid group with an amine (A) to form an amide bond and reacting the N-terminal amine with a carboxylic acid (CA) to form an amide bond, wherein the steps can be performed in either order. Also provided are an isolated salt of the universal dolastatin core for use in preparation of dolastatins, auristatins and related compounds. Also provided are a number of intermediates and process steps which are useful for the preparation of high purity dolastatin core and high purity dolastatin and auristatin compounds.

ONE-POT PROCESS FOR PREPARING INTERMEDIATE OF ANTIBODY-DRUG CONJUGATE

The present invention relates to a “one-pot process” for preparing intermediate of antibody-drug conjugate. The preparation process provided by the present invention is simple in operation, and needs no such steps like concentration, washing and filtratio

PROCESS FOR THE PREPARATION OF DRUG LINKER COMPOUNDS

This disclosure generally relates to novel processes for the preparation of drug linker compounds and compositions comprising such drug linker compounds. The presently disclosed methods for synthesizing Fmoc-Val-Cit-PABOH and related compounds have also been found to minimize formation of diastereomeric impurities.