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MilliporeSigma

803227

Sigma-Aldrich

Sulfo-MBS (m-maleimidobenzoyl-N-hydroxysulfosuccinimide ester)

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About This Item

Fórmula empírica (notación de Hill):
C15H9O9N2NaS
Número de CAS:
Peso molecular:
416.29
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:

assay

≥80%

form

powder

mol wt

416.3

reaction suitability

reagent type: cross-linking reagent

storage condition

desiccated

solubility

water: soluble

functional group

maleimide

shipped in

ambient

storage temp.

−20°C

SMILES string

O=C(C1=CC(N2C(C=CC2=O)=O)=CC=C1)ON3C(C(S(=O)([O-])=O)CC3=O)=O.[Na+]

InChI

1S/C15H10N2O9S.Na/c18-11-4-5-12(19)16(11)9-3-1-2-8(6-9)15(22)26-17-13(20)7-10(14(17)21)27(23,24)25;/h1-6,10H,7H2,(H,23,24,25);/q;+1/p-1

InChI key

LKUULGDICDGFIQ-UHFFFAOYSA-M

General description

MBS and its water-soluble analog Sulfo-MBS 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 simultaneously with the maleimide (sulfhydryl-targeted) reaction.

Features and Benefits

  • Reactive groups: sulfo-NHS ester and maleimide
  • Reactive towards: amino and sulfhydryl groups
  • Non-cleavable
  • Water-soluble (compare to MBS)
  • Membrane impermeable, allowing cell surface labeling

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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