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Sulfo-SMCC sodium is a commonly used hetero-bifunctional, noncleavable ADC crosslinker bearing N-hydroxysuccinimide (NHS) ester and maleimide groups to react with primary amines and sulfhydryl groups, respectively. Sulfo-SMCC is heterobifunctionalcrosslinker that contains N-hydroxysuccinimide (NHS) ester and maleimide groups that allow covalent conjugation of amine- and sulfhydryl-containing molecules. NHS esters react with primary amines at pH 7~9 to form amide bonds, while maleimides react with sulfhydryl groups at pH 6.5~7.5 to form stable thioether bonds. In aqueous solutions, NHS ester hydrolytic degradation is a competing reaction whose rate increases with pH. The maleimide group is more stable than the NHS-ester group but will slowly hydrolyze and loses its reaction specificity for sulfhydryls at pH values > 7.5. For these reasons, conjugations with these crosslinkers are usually performed at pH 7.2~7.5, with the NHS-ester (amine-targeted) reacted before or simultaneous with the maleimide (sulfhydryltargeted) reaction.
Molecular Weight | 436.37 |
Formula | C16H17N2NaO9S |
CAS Number | 92921-24-9 |
Solubility (25°C) | Water 2.5 mg/mL DMSO |
Storage | 2-8°C, protect from light, dry, sealed |
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