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803227

Sigma-Aldrich

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

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About This Item

Formule empirique (notation de Hill):
C15H9O9N2NaS
Numéro CAS:
Poids moléculaire :
416.29
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :

Essai

≥80%

Forme

powder

Poids mol.

416.3

Pertinence de la réaction

reagent type: cross-linking reagent

Conditions de stockage

desiccated

Solubilité

water: soluble

Groupe fonctionnel

maleimide

Conditions d'expédition

ambient

Température de stockage

−20°C

Chaîne 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

Clé InChI

LKUULGDICDGFIQ-UHFFFAOYSA-M

Description générale

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.

Caractéristiques et avantages

  • 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

Attention

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Antinuclear antibodies in the investigation of rheumatic diseases.
M J Fritzler
Bulletin on the rheumatic diseases, 35(6), 1-10 (1985-01-01)

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