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761524

Sigma-Aldrich

Dibenzocyclooctyne-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Synonym(s):

DBCO-NHS ester, DBCO-SE

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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW7467
MKCV7905
MKCV7904
MKCV4188
MKCT0153

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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)
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