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762040

Sigma-Aldrich

Dibenzocyclooctyne-sulfo-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C25H21N2NaO8S
Peso molecular:
532.50
Número MDL:
MFCD22572669
Código UNSPSC:
12352108
ID de la sustancia en PubChem:
329766600
NACRES:
NA.22

formulario

solid

idoneidad de la reacción

reaction type: click chemistry
reagent type: linker

mp

240-260 °C

temp. de almacenamiento

−20°C

cadena SMILES

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

Clave InChI

QXKHPYSXPCJSPR-UHFFFAOYSA-M

Categorías relacionadas

Aplicación

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Switchable supramolecular catalysis using DNA-templated scaffolds.
Garcia MAA, et al.
Chemical Communications (Cambridge, England), 52(10), 2153-2156 (2016)
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)
Optically Transparent Dense Colloidal Gels.
Zupkauskas M, et al.
Chemical Science (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
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
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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.

Click Chemistry in Drug Discovery

Drug discovery process by utilizing chemistry reaction of Cu(I)-catalyzed Huisgen 1,3-dipolar cycloaddition of terminal alkynes with organoazides to yield 1,4-disubstituted 1,2,3-triazoles.

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