Accéder au contenu
Merck
Toutes les photos(1)

Documents

761524

Sigma-Aldrich

Dibenzocyclooctyne-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Synonyme(s) :

DBCO-NHS ester, DBCO-SE

Se connecterpour consulter vos tarifs contractuels et ceux de votre entreprise/organisme
Toutes les photos(1)

About This Item

Formule empirique (notation de Hill):
C23H18N2O5
Poids moléculaire :
402.40
Numéro MDL:
MFCD24386367
Code UNSPSC :
12352108
ID de substance PubChem :
329766555
Nomenclature NACRES :
NA.22

Forme

solid

Capacité de réaction

reaction type: click chemistry

Pertinence de la réaction

reagent type: cross-linking reagent

Pf

149-157 (decomposition)

Groupe fonctionnel

NHS ester

Température de stockage

−20°C

Chaîne SMILES 

O=C(CCC(ON(C(CC1)=O)C1=O)=O)N2CC3=C(C=CC=C3)C#CC4=C2C=CC=C4

InChI

1S/C23H18N2O5/c26-20(13-14-23(29)30-25-21(27)11-12-22(25)28)24-15-18-7-2-1-5-16(18)9-10-17-6-3-4-8-19(17)24/h1-8H,11-15H2

Clé InChI

XCEBOJWFQSQZKR-UHFFFAOYSA-N

Catégories apparentées

Description générale

DBCO-NHS ester is commonly used in bioconjugation. It consists of an NHS ester that reacts with primary amines on biomolecules and an alkyne group that allows for a specific reaction with molecules containing azides. This reaction is carried out through a copper-free click chemistry process called strain-promoted alkyne-azide cycloaddition.

Application

Dibenzocyclooctyne-N-hydroxysuccinimidyl ester is commonly used:
  • In the modification and labeling of biomolecules such as antibodies and streptavidin by introducing DBCO groups onto their surfaces
  • As a cross linker to conjugate peptide antigens onto the surface of poly(lactic-co-glycolic acid) (PLGA) nanoparticles

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

Déjà en possession de ce produit ?

Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Zwitterionic-silane copolymer for ultra stable and bright biomolecular probes based on fluorescent quantum dot nanoclusters
Dembele F, et al.
ACS Applied Materials & Interfaces (2017)
DNA-Assembled Core-Satellite Upconverting-Metal-Organic Framework Nanoparticle Superstructures for Efficient Photodynamic Therapy.
He L, et al.
Small (2017)
Graphene Oxide Nanosheets Modified with Single-Domain Antibodies for Rapid and Efficient Capture of Cells.
Chen GY, et al.
Chemistry?A European Journal , 21(48), 17178-17183 (2015)
Polymeric coating of silica microspheres for biological applications: suppression of non-specific binding and functionalization with biomolecules
D Brambilla, et al.
Polymers, 14, 730-730 (2022)
Hao Ma et al.
Biomaterials, 255, 120205-120205 (2020-06-24)
Three biorthogonal click reactions, a photoinitiated thiol-yne reaction, an azide-alkyne cycloaddition, and a methyltetrazine-transcyclooctene Diels Alder, were used to independently control the presentation of several bioactive proteins to valvular interstitial cells (VICs) in hydrogel scaffolds. Tethered fibroblast growth factor (FGF-2)
Afficher tous les articles scientifiques apparentés

Articles

Copper-Free Click Chemistry

Copper-free click chemistry is an alternative approach to click chemistry that proceeds at a lower activation barrier and is free of cytotoxic transition metal catalysts.

Click Chemistry in Drug Discovery

Drug discovery process by utilizing chemistry reaction of Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of terminal alkynes with organoazides to yield 1,4-disubstituted 1,2,3-triazoles.

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

Contacter notre Service technique