Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

762040

Sigma-Aldrich

Dibenzocyclooctyne-sulfo-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Synonym(s):

DBCO-sulfo-NHS ester, DBCO-sulfo-SE

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

About This Item

Empirical Formula (Hill Notation):
C25H21N2NaO8S
Molecular Weight:
532.50
MDL number:
MFCD22572669
UNSPSC Code:
12352108
PubChem Substance ID:
329766600
NACRES:
NA.22

form

solid

reaction suitability

reaction type: click chemistry
reagent type: linker

mp

240-260 °C

storage temp.

−20°C

SMILES string

O=C(CCCCC(ON(C(CC1S(=O)(O[Na])=O)=O)C1=O)=O)N2CC3=C(C=CC=C3)C#CC4=C2C=CC=C4

InChI

1S/C25H22N2O8S.Na/c28-22(11-5-6-12-24(30)35-27-23(29)15-21(25(27)31)36(32,33)34)26-16-19-9-2-1-7-17(19)13-14-18-8-3-4-10-20(18)26;/h1-4,7-10,21H,5-6,11-12,15-16H2,(H,32,33,34);/q;+1/p-1

InChI key

QXKHPYSXPCJSPR-UHFFFAOYSA-M

Related Categories

Application

Water soluble succinimidyl ester/NHS functionalized cyclooctyne derivative for incorporation of the cyclooctyne moiety into amine containing compounds or biomolecules. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne 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.
Dibenzocyclooctyne-sulfo-N-hydroxysuccinimidyl ester may be used for the covalent modification of nano-sized metal-organic frameworks (NMOFs) with nucleic acids via click chemistry during the synthesis stimuli-responsive DNA-gated NMOFs. These NMOFs can act as carriers of a fluorescent agent or anticancer drug, making them highly useful in targeted drug release system.

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

Instructing cells with programmable peptide DNA hybrids.
Freeman R, et al.
Nature Communications, 8 (2017)
Chen Chen et al.
Small (Weinheim an der Bergstrasse, Germany), 15(43), e1901014-e1901014 (2019-09-04)
Exosomes are endosome-derived vesicles enriched in body fluids such as urine, blood, and saliva. So far, they have been recognized as potential biomarkers for cancer diagnostics. However, the present single-variate analysis of exosomes has greatly limited the accuracy and specificity
Fang Chen et al.
Biomaterials, 255, 120176-120176 (2020-06-20)
Biomaterials that mimic corneal stroma could decrease the need for donor corneal tissue and could decrease the prevalence of complications associated with corneal transplantation, including infection and rejection. We developed a bio-orthogonally crosslinked hyaluronate-collagen hydrogel which can fill corneal defects
Tethering Growth Factors to Collagen Surfaces Using Copper-free Click Chemistry: Surface Characterization and In Vitro Biological Response.
Lee HJ, et al.
ACS Applied Materials & Interfaces, 9(28), 23389-23399 (2017)
Stimuli-Responsive Nucleic Acid-Functionalized Metal-Organic-Framework Nanoparticles Using pH-and Metal-Ion Dependent DNAzymes as Locks.
Chen WH, et al.
Chemical Science (2017)
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