803243
Sulfo-SMPB (sulfosuccinimidyl 4-(N-maleimidophenyl)butyrate)
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About This Item
Fórmula empírica (Notação de Hill):
C18H15N2O9SNa
Peso molecular:
458.37
Número MDL:
Código UNSPSC:
12352200
ID de substância PubChem:
NACRES:
NA.22
Produtos recomendados
forma
powder
Nível de qualidade
peso molecular
458.38
adequação da reação
reagent type: cross-linking reagent
condição de armazenamento
desiccated
solubilidade
water: soluble
grupo funcional
maleimide
Condições de expedição
ambient
temperatura de armazenamento
−20°C
cadeia de caracteres SMILES
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
chave InChI
LSZBIKKARBHBPA-UHFFFAOYSA-M
Descrição geral
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.
Características e benefícios
- 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
Atenção
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 classe de armazenamento
11 - Combustible Solids
Classe de risco de água (WGK)
WGK 3
Ponto de fulgor (°F)
Not applicable
Ponto de fulgor (°C)
Not applicable
Certificados de análise (COA)
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