N-hydroxysulfosuccinimide active esters: bis(N-hydroxysulfosuccinimide) esters of two dicarboxylic acids are hydrophilic, membrane-impermeant, protein cross-linkers

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Abstract
N-hydroxysulfosuccinimide, a new hydrophilic ligand for the preparation of active esters was synthesized and characterized. This ligand was incorporated into 2 new protein cross-linking reagents, 3,3''-dithiobis(sulfosuccinimidyl propionate) and bis(sulfosuccinimidyl) suberate. In experiments with rabbit muscle aldolase, both of these reagents are highly efficient protein cross-linkers at physiological pH and 3,3''-dithiobis(sulfosuccinimidyl propionate) is quantitatively cleavable by reduction under mild conditions. In experiments with intact human erythrocytes and erythrocyte membranes, both reagents are membrane impermeant and when erythrocytes are treated with either reagent, both cross-link subunits of the anion channel (band 3) to covalent dimers at the extracytoplasmic membrane face.

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