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Merck

803383

Sigma-Aldrich

LC-SMCC (succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxy-(6-amidocaproate))

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About This Item

Fórmula empírica (notación de Hill):
C22H29N3O7
Peso molecular:
447.48
Número MDL:
Código UNSPSC:
12352106
ID de la sustancia en PubChem:
NACRES:
NA.22

Ensayo

≥90%

Nivel de calidad

Formulario

powder

mol peso

447.48

idoneidad de la reacción

reagent type: cross-linking reagent

condiciones de almacenamiento

desiccated

solubilidad

DMSO or DMF: soluble

grupo funcional

NHS ester
maleimide

Condiciones de envío

ambient

temp. de almacenamiento

2-8°C

cadena SMILES

O=C(CCC1=O)N1OC(CCCCCNC(C2CCC(CN3C(C=CC3=O)=O)CC2)=O)=O

InChI

1S/C22H29N3O7/c26-17-9-10-18(27)24(17)14-15-5-7-16(8-6-15)22(31)23-13-3-1-2-4-21(30)32-25-19(28)11-12-20(25)29/h9-10,15-16H,1-8,11-14H2,(H,23,31)

Clave InChI

IHVODYOQUSEYJJ-UHFFFAOYSA-N

Descripción general

LC-SMCC 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

Características y beneficios

  • Reactive groups: NHS ester and maleimide
  • Reactive toward: amino and sulfhydryl groups
  • Long-chain variety of SMCC
  • High purity, crystalline reagent can be used to create high-purity maleimide-activated derivatives
  • Non-cleavable
  • Water-insoluble (dissolve first in DMF or DMSO)
  • Cyclohexane bridge confers added stability to the maleimide group making LC-SMCC an ideal crosslinking agent for maleimide activation of proteins. Maleimide groups are stable for 64 hours in 0.1 M sodium phosphate buffer, pH 7 at 4°C.

Precaución

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 clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Salvatore C Ruffolo et al.
The Journal of biological chemistry, 278(27), 25039-25045 (2003-05-02)
Caspase-8 cleaves BID to tBID, which targets mitochondria and induces oligomerization of BAX and BAK within the outer membrane, resulting in release of cytochrome c from the organelle. Here, we have initiated these steps in isolated mitochondria derived from control

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