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Sigma-Aldrich

Dibenzocyclooctyne-sulfo-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Synonym(s):

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

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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)

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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)
Longyi Zhu et al.
Chemical science, 9(9), 2559-2566 (2018-05-08)
Aggregation-induced emission (AIE) can be generated due to the restriction of intramolecular motions. The controllable assembly of fluorogens with AIE properties (AIEgens) is able to provide a new opportunity for precise manipulation of fluorescent signal transduction. Here, a tetrapod DNA
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
ATP?Responsive Aptamer?Based Metal?Organic Framework Nanoparticles (NMOFs) for the Controlled Release of Loads and Drugs.
Chen WH, et al.
Advances in Functional Materials (2017)
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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.

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