803243
Sulfo-SMPB (sulfosuccinimidyl 4-(N-maleimidophenyl)butyrate)
Sign Into View Organizational & Contract Pricing
All Photos(1)
About This Item
Empirical Formula (Hill Notation):
C18H15N2O9SNa
Molecular Weight:
458.37
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
form
powder
Quality Level
mol wt
458.38
reaction suitability
reagent type: cross-linking reagent
storage condition
desiccated
solubility
water: soluble
functional group
maleimide
shipped in
ambient
storage temp.
−20°C
SMILES string
O=C1CC(S(=O)([O-])=O)C(N1OC(CCCC2=CC=C(N3C(C=CC3=O)=O)C=C2)=O)=O.[Na+]
InChI
1S/C18H16N2O9S.Na/c21-14-8-9-15(22)19(14)12-6-4-11(5-7-12)2-1-3-17(24)29-20-16(23)10-13(18(20)25)30(26,27)28;/h4-9,13H,1-3,10H2,(H,26,27,28);/q;+1/p-1
InChI key
LSZBIKKARBHBPA-UHFFFAOYSA-M
General description
SMPB and its water-soluble analog Sulfo-SMPB 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 simultaneous with the maleimide (sulfhydryl-targeted) reaction.
Features and Benefits
- Reactive groups: sulfo-NHS ester and maleimide
- Reactive towards: amino and sulfhydryl groups
- Extended chain length limits steric hindrance
- Non-cleavable
- Water-soluble (compare to SMPB)
- Membrane impermeable, allowing for cell surface labeling
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
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Choose from one of the most recent versions:
Certificates of Analysis (COA)
Lot/Batch Number
Don't see the Right Version?
If you require a particular version, you can look up a specific certificate by the Lot or Batch number.
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Customers Also Viewed
Aygun A Mamedova et al.
The Journal of biological chemistry, 279(22), 23830-23836 (2004-03-24)
The mechanism coupling electron transfer and proton pumping in respiratory complex I (NADH-ubiquinone oxidoreductase) has not been established, but it has been suggested that it involves conformational changes. Here, the influence of substrates on the conformation of purified complex I
Xiao-Qi Wang et al.
The Journal of biological chemistry, 277(49), 47028-47034 (2002-10-02)
Although caveolin-1 is thought to facilitate the interaction of receptors and signaling components, its role in epidermal growth factor receptor (EGFR) signaling remains poorly understood. Ganglioside GM3 inhibits EGFR autophosphorylation and may thus affect the interaction of caveolin-1 and the
Silvia Goldoni et al.
The Journal of biological chemistry, 279(8), 6606-6612 (2003-12-09)
It has been reported that decorin and its protein core can have molecular masses nearly double the size of those previously published, suggesting a dimeric structure. In this study we tested whether biologically active decorin and its glycoprotein core would
Zhenhui Chen et al.
The Journal of biological chemistry, 278(48), 48348-48356 (2003-09-16)
Heterobifunctional thiol to amine cross-linking agents were used to gain new insights on the dynamics and conformational factors governing the interaction between the cardiac Ca2+ pump (SERCA2a) and phospholamban (PLB). PLB is a small protein inhibitor of SERCA2a that reduces
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