761524

Sigma-Aldrich

Dibenzocyclooctyne-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Synonym(s):
DBCO-SE, DBCO-NHS ester
Empirical Formula (Hill Notation):
C23H18N2O5
Molecular Weight:
402.40
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

reaction suitability

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

mp

149-157 (decomposition)

storage temp.

−20°C

SMILES string

O=C(CCC(=O)N1Cc2ccccc2C#Cc3ccccc13)ON4C(=O)CCC4=O

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

Application

Succinimidyl ester (NHS, amine reactive) functionalized cyclooctyne derivative for incorporation of the cyclooctyne moiety into amine containing compounds or biomolecules. Cyclooctynes are useful in strain-promoted copper-free click chemistry cycloaddition reactions. This dibenzocyclooctyne will react with azide functionalized compounds or biomolecules without the need for a Cu(I) catalyst to result in a stable triazole linkage.

Applications Include:
  • Protein-peptide conjugates
  • Antibody-enzyme or antibody-drug conjugates
  • Protein or peptide-oligonucleotide conjugates
  • Surface modification

Packaging

1, 5, 50 mg in clear glass bottle

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

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)...
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)
DNA-Assembled Core-Satellite Upconverting-Metal-Organic Framework Nanoparticle Superstructures for Efficient Photodynamic Therapy.
He L, et al.
Small (2017)
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)
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)
Articles
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.
Read More

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

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.