Phenyl, bromo-maleimide as a coupling group for conjugation to sulfhydryl group

Abstract

The invention pertains to the creation of two new classes of compounds, referred to as “phenyl, bromo-maleimide acids” and “Phenyl, bromo-maleimide amines”, which are derivatized from the maleimide, C2H2(CO)2NH (2,5-pyrroledione) and have the backbone structure of formula I and II below, where n is 0-6. In the maleimide ring, a hydrogen in the 3,4-imide (C2H2) is substituted by a bromide and the nitrogen is bonded to a phenyl group, which is bonded to a carboxylic acid or amine. The invention also pertains to the use of these two classes of compounds to tag molecules with a Br,Ph-maleimide group or to synthesize hetrobifunctional linkers with a Br,Ph-maleimide group for conjugating various molecules to the sulfhydryl groups of cysteine residues in proteins, peptides, nanoparticles, or cells. Specifically, the Br,Ph-maleimide group has the structure of formula (III):

Dependencies are inferred from the claim text.