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Documentos Principais

803227

Sigma-Aldrich

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

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About This Item

Fórmula empírica (Notação de Hill):
C15H9O9N2NaS
Número CAS:
Peso molecular:
416.29
Número MDL:
Código UNSPSC:
12352200
ID de substância PubChem:

Ensaio

≥80%

Formulário

powder

peso molecular

416.3

adequação da reação

reagent type: cross-linking reagent

condição de armazenamento

desiccated

solubilidade

water: soluble

grupo funcional

maleimide

Condições de expedição

ambient

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

chave InChI

LKUULGDICDGFIQ-UHFFFAOYSA-M

Descrição geral

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.

Características e benefícios

  • 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

Atenção

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable


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