CAS 79886-55-8

N-succinimidyl 4-(4-maleimidophenyl)-butyrate

Description:

N-succinimidyl 4-(4-maleimidophenyl)-butyrate, commonly referred to as SMCC, is a chemical compound widely used in bioconjugation and protein labeling applications. It features a succinimidyl ester group that facilitates the formation of stable amide bonds with primary amines, making it particularly useful for conjugating proteins, peptides, or other biomolecules. The maleimide group in its structure allows for selective reaction with thiol groups, enabling the formation of thioether linkages. This dual reactivity makes SMCC a versatile crosslinker in the development of antibody-drug conjugates and other bioconjugates. The compound is typically soluble in organic solvents and exhibits stability under appropriate storage conditions. Its reactivity can be influenced by factors such as pH and the presence of competing nucleophiles. As with many chemical reagents, proper handling and safety precautions are essential, as it may pose risks such as skin and eye irritation. Overall, SMCC is a valuable tool in the fields of biochemistry and molecular biology for creating complex biomolecular structures.

Formula: C₁₈H₁₆N₂O₆

InChI: InChI=1/C18H16N2O6/c21-14-8-9-15(22)19(14)13-6-4-12(5-7-13)2-1-3-18(25)26-20-16(23)10-11-17(20)24/h4-9H,1-3,10-11H2

SMILES: C(Cc1ccc(cc1)N1C(=O)C=CC1=O)CC(=O)ON1C(=O)CCC1=O

Synonyms:

• 4-(4-Maleimidophenyl)butyric acid N-hydroxysuccinimide ester
• Succinimdyl-4-(p-maleimidophenyl)butyrate
• 1-(4-{4-[(2,5-dioxopyrrolidin-1-yl)oxy]-4-oxobutyl}phenyl)-1H-pyrrole-2,5-dione

2,5-Dioxopyrrolidin-1-yl 4-(4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)phenyl)butanoate

CAS: 79886-55-8

Formula: C₁₈H₁₆N₂O₆

Purity: 97%

Color and Shape: Solid

Molecular weight: 356.3294

Ref: IN-DA003TCC

SMPB Crosslinker

CAS: 79886-55-8

SMPB crosslinker reacts with sulfhydryl/amino groups, has a longer chain than MBS, and a non-cleavable spacer arm.

Formula: C₁₈H₁₆N₂O₆

Purity: 98%

Color and Shape: Solid

Molecular weight: 356.33

Ref: TM-T19943

Succinimidyl 4-(4-maleimidophenyl)butyrate

CAS: 79886-55-8

Succinimidyl 4-(4-maleimidophenyl)butyrate

Formula: C₁₈H₁₆N₂O₆

Purity: 99%

Color and Shape: light yellow crystalline powder

Molecular weight: 356.33g/mol

Ref: 54-BICL200

N-Succinimidyl 4-(p-maleimidophenyl)butyrate

CAS: 79886-55-8

N-Succinimidyl 4-(p-maleimidophenyl)butyrate is a fatty acid that has been shown to regulate the effector proteins of cell surface receptors. It has been shown to be site specific, with water permeability and a molecule size of about 200 Daltons. It is able to bind to the regulatory sites on proteins and inhibit their function. The binding of N-succinimidyl 4-(p-maleimidophenyl)butyrate to antibodies can cause an antibody response in humans and other mammals. Additionally, this fatty acid can also be used as a substrate for protein synthesis. N-Succinimidyl 4-(p-maleimidophenyl)butyrate binds to the subunits of proteins by hydrogen bonding or hydrophobic interactions, which are necessary for protein synthesis. This compound has been shown to inhibit the messenger RNA (mRNA) production in Galleria mellonella larvae,

Formula: C₁₈H₁₆N₂O₆

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 356.33 g/mol

Ref: 3D-FS27895

N-SUCCINIMIDYL 4-(4-MALEIMIDOPHENYL)BUTYRATE

CAS: 79886-55-8

Purity: 98%

Molecular weight: 356.3340149

Ref: 10-F842878

N-Succinimidyl 4-(p-Maleimidophenyl)butyrate

Controlled Product

CAS: 79886-55-8

Applications A sulfhydryl and amino reactive heterobifunctional protein crosslinking reagent. Spacer Arm: 11.6 Angstroms
References Martin, F.J., et al.: J. Biol. Chem., 257, 286 (1982), Teale, J.M., et al.: J. Mol. Cell Immunol., 2, 283 (1986)

Formula: C₁₈H₁₆N₂O₆

Color and Shape: Neat

Molecular weight: 356.33

Ref: TR-S690460