761524

Dibenzocyclooctyne-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

• Synonym(s): DBCO-NHS ester, DBCO-SE
• Empirical Formula (Hill Notation): C₂₃H₁₈N₂O₅
• Molecular Weight: 402.40
• MDL number: MFCD24386367
• UNSPSC Code: 12352108
• PubChem Substance ID: 329766555
• NACRES: NA.22

Properties

• 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

Description

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable