761516
Dibenzocyclooctyne-acid
storage temp.:-20°C, 95%
Synonym(s):
DBCO-Acid
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About This Item
Empirical Formula (Hill Notation):
C21H19NO3
Molecular Weight:
333.38
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352106
MDL number:
Assay:
95%
Form:
solid
InChI
1S/C21H19NO3/c23-20(11-5-6-12-21(24)25)22-15-18-9-2-1-7-16(18)13-14-17-8-3-4-10-19(17)22/h1-4,7-10H,5-6,11-12,15H2,(H,24,25)
SMILES string
O=C(CCCCC(O)=O)N1CC2=C(C=CC=C2)C#CC3=C1C=CC=C3
InChI key
NIRLBCOFKPVQLM-UHFFFAOYSA-N
assay
95%
form
solid
Quality Level
reaction suitability
reagent type: linker
mp
118-125 °C
functional group
carboxylic acid
storage temp.
−20°C
General description
Acid functionalized cyclooctyne derivative. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne click chemistry reactions. This azadibenzocyclooctyne will react with azide functionalized compounds or biomolecules without the need for a Cu(I) catalyst to result in a stable triazole linkage.
Application
Dibenzocyclooctyne-acid may be used for the surface modification of eight-arm poly(ethylene glycol), to make it susceptible to strain promoted alkyne-azide cycloaddition (SPAAC) with PEG-bis-azide leading to the formation of hydrogels. These hydrogels are useful for protein immobilization.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Ratiometric Fluorescence Azide?Alkyne Cycloaddition for Live Mammalian Cell Imaging.
Fu H, et al.
Analytical Chemistry, 87(22), 11332-11336 (2015)
Chen Guo et al.
Acta biomaterialia, 56, 80-90 (2017-04-10)
Hydrogels are facile architectures for the controlled presentation of proteins with far-reaching applications, from fundamental biological studies in three-dimensional culture to new regenerative medicine and therapeutic delivery strategies. Here, we demonstrate a versatile approach for spatially-defined presentation of engineered proteins
Seyed Mohammad Mahdi Dadfar et al.
Small (Weinheim an der Bergstrasse, Germany), 14(21), e1800131-e1800131 (2018-04-24)
Different types of click chemistry reactions are proposed and used for the functionalization of surfaces and materials, and covalent attachment of organic molecules. In the present work, two different catalyst-free click approaches, namely azide-alkyne and thiol-alkyne click chemistry are studied
Flexible synthesis of cationic peptide?porphyrin derivatives for light-triggered drug delivery and photodynamic therapy.
Dondi R, et al.
Organic & Biomolecular Chemistry, 14(48), 11488-11501 (2016)
Bio-orthogonal conjugation and enzymatically triggered release of proteins within multi-layered hydrogels.
Guo C, et al.
Acta Biomaterialia (2017)
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