Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

761524

Sigma-Aldrich

Dibenzocyclooctyne-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Synonym(s):

DBCO-NHS ester, DBCO-SE

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C23H18N2O5
Molecular Weight:
402.40
MDL number:
MFCD24386367
UNSPSC Code:
12352108
PubChem Substance ID:
329766555
NACRES:
NA.22

form

solid

reaction suitability

reaction type: click chemistry
reagent type: cross-linking reagent

mp

149-157 (decomposition)

functional group

NHS ester

storage temp.

−20°C

SMILES string

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

InChI key

XCEBOJWFQSQZKR-UHFFFAOYSA-N

Related Categories

General description

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Preparation of single-and double-oligonucleotide antibody conjugates and their application for protein analytics
J Wiener, et al.
Scientific reports, 10, 1457-1457 (2020)
Nanoparticles functionalized with collagenase exhibit improved tumor accumulation in a murine xenograft model.
Murty S, et al.
Particle & Particle Systems Characterization, 31(12), 1307-1312 (2014)
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)
Vaccination with nanoparticles combined with micro-adjuvants protects against cancer
MO Mohsen, et al.
Journal for Immunotherapy of Cancer, 7, 1-12 (2019)
View All Related Papers

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.

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.

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.

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.

See All

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