Sulfo-SMPB (sulfosuccinimidyl 4-(N-maleimidophenyl)butyrate)

ALDRICH/803243

Empirical Formula (Hill Notation): C₁₈H₁₅N₂O₉SNa
Molecular Weight: 458.37
MDL Number: MFCD00054981
Linear Formula: C₁₈H₁₅N₂O₉SNa
Product Type: Chemical

Catalog Number	PKG Qty.	Price	Quantity


45-803243-50MG	50 mg	$342.00 1/EA		Add To Favorites

Properties
Descriptions
Safety Info.
Basic Data

form	powder
functional group	maleimide
InChI	1S/C18H16N2O9S.Na/c21-14-8-9-15(22)19(14)12-6-4-11(5-7-12)2-1-3-17(24)29-20-16(23)10-13(18(20)25)30(26,27)28;/h4-9,13H,1-3,10H2,(H,26,27,28);/q;+1/p-1
InChI key	LSZBIKKARBHBPA-UHFFFAOYSA-M
mol wt	458.38
Quality Level	100
reaction suitability	reagent type: cross-linking reagent
shipped in	ambient
SMILES string	O=C1CC(S(=O)([O-])=O)C(N1OC(CCCC2=CC=C(N3C(C=CC3=O)=O)C=C2)=O)=O.[Na+]
solubility	water: soluble
storage condition	desiccated
storage temp.	−20°C

Caution:	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.
Features and Benefits:	• Reactive groups: sulfo-NHS ester and maleimide • Reactive towards: amino and sulfhydryl groups • Extended chain length limits steric hindrance • Non-cleavable • Water-soluble (compare to SMPB) • Membrane impermeable, allowing for cell surface labeling
General description:	SMPB and its water-soluble analog Sulfo-SMPB are heterobifunctional crosslinkers that contain 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, 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 > 7.5. For these reasons, conjugation experiments involving these crosslinkers 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.

RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Storage Temp.	−20°C
UNSPSC	12352200

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