803383
LC-SMCC (succinimidyl-4-(N-maleimidomethyl)cyclohexane-1-carboxy-(6-amidocaproate))
Sign In to View Organizational & Contract Pricing.
Select a Size
About This Item
Empirical Formula (Hill Notation):
C22H29N3O7
Molecular Weight:
447.48
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352106
MDL number:
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)
SMILES string
O=C(CCC1=O)N1OC(CCCCCNC(C2CCC(CN3C(C=CC3=O)=O)CC2)=O)=O
InChI key
IHVODYOQUSEYJJ-UHFFFAOYSA-N
assay
≥90%
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
Quality Level
Related Categories
Disclaimer
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.
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.
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
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
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
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service