SMPH (succinimidyl-6-((b-maleimidopropionamido)hexanoate)

C₁₇H₂₁N₃O₇

379.36

MFCD01863460

329768822

SMPH is a heterobifunctional crosslinker with 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 the maleimides react with sulfhydryl groups at pH 6.5-7.5 to form stable thioether bonds. In aqueous solutions, hydrolytic degradation of the NHS ester 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 also lose its reaction specificity for sulfhydryls at pH values greater than 7.5. For these reasons, conjugation experiments involving this type of heterobifunctional crosslinker are usually performed at pH 7.2-7.5, with the NHS-ester (amine-targeted) reaction being accomplished before or simultaneous with the maleimide (sulfhydryl-targeted) reaction.

This product is sensitive to moisture. The vial is packaged in a resealable bag with a desiccant to reduce exposure to moisture. After cold storage, equilibrate the vial to room temperature before opening to reduce condensation inside the vial. Make fresh solutions. Storage of stock solutions is not recommended. After use, return the vial to the resealable bag. Close the bag and store the product at the recommended temperature.

100

≥90%

powder

379.36

reagent type: cross-linking reagent

desiccated

DMSO or DMF: soluble

ambient

2-8℃

O=C(CCCCCNC(CCN1C(C=CC1=O)=O)=O)ON2C(CCC2=O)=O

1S/C17H21N3O7/c21-12(9-11-19-13(22)5-6-14(19)23)18-10-3-1-2-4-17(26)27-20-15(24)7-8-16(20)25/h5-6H,1-4,7-11H2,(H,18,21)

WCMOHMXWOOBVMZ-UHFFFAOYSA-N

GHS07

Warning

H315 - H319 - H335

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Respiratory system

11 - Combustible Solids

WGK 3