64191-06-6

Basic information

• Product Name: 4-N-Maleimidobenzoic acid-NHS
• Synonyms: 4-N-Maleimidobenzoic acid-NHS;4-MaleiMidobenzoic acid-NHS ester;2,5-dioxopyrrolidin-1-yl 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoate;4-Mal-Bz-NHS
• CAS NO: 64191-06-6
• Molecular Formula: C₁₅H₁₀N₂O₆
• Molecular Weight: 314.2497
• Mol File: 64191-06-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 205-207 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• Boiling Point: 523.0±52.0 °C(Predicted)
• Appearance: /
• Density: 1.59±0.1 g/cm3(Predicted)
• PKA: -4.69±0.20(Predicted)
• CAS DataBase Reference: 4-N-Maleimidobenzoic acid-NHS(CAS DataBase Reference)
• NIST Chemistry Reference: 4-N-Maleimidobenzoic acid-NHS(64191-06-6)
• EPA Substance Registry System: 4-N-Maleimidobenzoic acid-NHS(64191-06-6)

Safety Data

• Hazardous Substances Data: 64191-06-6(Hazardous Substances Data)

Usage

General Description

4-N-Maleimidobenzoic acid-NHS is a chemical compound used in bioconjugation reactions to covalently link proteins or peptides to other molecules. It contains a maleimide group which specifically reacts with free thiol groups in proteins to form stable thioether bonds. The NHS functional group allows for easy attachment to amine groups on the target molecules. 4-N-Maleimidobenzoic acid-NHS is commonly used in the development of protein conjugates for various research and diagnostic applications, including antibody labeling, protein immobilization, and drug delivery systems. Its high reactivity and specificity make it a valuable tool in bioconjugation chemistry.

Upstream product

• 108-31-6 maleic anhydride 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 150-13-0 4-amino-benzoic acid 
• 17057-04-4 N-(4-carboxyphenyl)maleimide 
• 5432-04-2 N-(4-carboxyphenyl)maleamic acid 
• 5672-89-9 N-trifluoroacetoxy succinimide 

Relevant articles and documents

Synthesis, characterization, and targeted chemotherapy of SCT200-linker-monomethyl auristatin E conjugates

Antibody-drug conjugates (ADCs) are currently among the most successful and important strategies for treating patients with solid tumors. ADCs are composed of a monoclonal antibody and warhead, which are conjugated via a linker. Currently, monomethyl auristatin E (MMAE) is the most widely applied warhead in the development of ADCs. However, MMAE-based ADCs are generally constructed using the MC-VC-PABC linker, and this design has limited structural diversity and some disadvantages. Accordingly, in this study, we generated three types of novel linker-MMAE (with alterations in the spacer, catabolizing area, and self-immolative compared with MC-VC-PABC-MMAE) in ADCs, termed SCT200-linker-MMAE conjugates, and then evaluated the linker-drug plasma stability and the rate of drug release by cathepsin B. The binding ability, internalization rates, and efficacy of all SCT200-linker-MMAE ADCs were systematically studied, and the expression of apoptosis-associated proteins and the therapeutic efficacies of SCT200-M-2, -C-2, and -C-4 were evaluated. The results showed that the activities of some of these ADCs were increased for epidermal growth factor receptor-positive tumors. Moreover, the novel linkers designed in this study can be linked with other antibodies to treat other types of cancer. Overall, these findings provide important insights into the application of SCT200-based linkers in ADCs.

Practical synthesis of maleimides and coumarin-linked probes for protein and antibody labelling via reduction of native disulfides

The cellular tracking, detection and sensing of protein or antibody movement are important aspects to advance our understanding of biomolecular interactions and activity. Antibodies modified with fluorescent dyes are also valuable tools, especially in immunology research. We describe here a proof-of-principle study of a new water-soluble coumarin probe with a maleimide thiol-reacting unit to fluorescently tag biomolecules. Highlights include: (1) a convenient water-based preparation of N-substituted maleimides, (2) a one-pot preparation of activated maleimido-esters, and (3) a bio-conjugation protocol for the selenol-promoted reduction of native disulfide bonds and the 'site-specific' labelling of antibodies with no significant loss of activity.

Facile synthesis of reagents containing a terminal maleimido ligand linked to an active ester

Condensation of ω-amino acids with maleic anhydride to yield maleamino acids and subsequent esterification with N-hydroxysuccinimide, 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine, or pentafluorophenol to give the corresponding esters in a one pot procedure are described. The reagents can be isolated and purified without chromatography in 7-55% yields.