N-Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate丨CAS 64987-85-5

N-Succinimidyl 4-(N-maleimidomethyl)cyclohexane-1-carboxylate (commonly known as SMCC) is a widely used bifunctional crosslinking reagent in bioconjugation, pharmaceutical research, and protein engineering. It is primarily employed to link proteins, peptides, antibodies, or other biomolecules via amine and thiol functional groups, enabling the synthesis of antibody-drug conjugates (ADCs), protein-drug conjugates, and targeted therapeutics. SMCC is also used in immobilization of enzymes or ligands onto solid supports for diagnostics, biosensors, and affinity chromatography. Its selective reactivity towards primary amines (via the NHS ester) and sulfhydryl groups (via the maleimide moiety) allows precise, site-specific conjugation, which is crucial in maintaining biological activity and functionality of the conjugated molecules.

The benefits of SMCC arise from its bifunctional reactivity, chemical stability, and specificity. The NHS ester allows efficient conjugation with primary amines under mild aqueous conditions, while the maleimide group reacts selectively with thiols, enabling targeted and stable crosslinking. This dual functionality minimizes side reactions and ensures reproducibility in bioconjugation processes. SMCC provides robust and stable linkages, maintaining the structural integrity and activity of proteins and other biomolecules. Its versatility in forming antibody-drug conjugates, enzyme immobilization, and targeted delivery systems makes it an indispensable tool in pharmaceutical development, diagnostics, and biochemical research.