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Merck
CN

762040

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
NACRES:
NA.22
PubChem Substance ID:
329766600
UNSPSC Code:
12352108
MDL number:
MFCD22572669
Assay:
≥90.0 %
Form:
solid

Key Documents

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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

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 key

QXKHPYSXPCJSPR-UHFFFAOYSA-M

assay

≥90.0 %

form

solid

reaction suitability

reaction type: click chemistry, reagent type: linker

bp

30 -100 °C

mp

240-260 °C

solubility

water: soluble at 20 °C

storage temp.

−20°C

Quality Level

100

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ9648
MKCZ3488
MKCZ2076
MKCX7752
MKCX2357

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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
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
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)
Switchable supramolecular catalysis using DNA-templated scaffolds.
Garcia MAA, et al.
Chemical Communications (Cambridge, England), 52(10), 2153-2156 (2016)
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