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Sigma-Aldrich

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

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Empirical Formula (Hill Notation):
C22H29N3O7
Molecular Weight:
447.48
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Assay

≥90%

Quality Level

form

powder

mol wt

447.48

reaction suitability

reagent type: cross-linking reagent

storage condition

desiccated

solubility

DMSO or DMF: soluble

functional group

NHS ester
maleimide

shipped in

ambient

storage temp.

2-8°C

SMILES string

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)

InChI key

IHVODYOQUSEYJJ-UHFFFAOYSA-N

Related Categories

General description

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

Features and Benefits

  • 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.

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(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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