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761524

Sigma-Aldrich

Dibenzocyclooctyne-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Sinonimo/i:

DBCO-NHS ester, DBCO-SE

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82,80 €
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402,00 €

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About This Item

Formula empirica (notazione di Hill):
C23H18N2O5
Peso molecolare:
402.40
Numero MDL:
MFCD24386367
Codice UNSPSC:
12352108
ID PubChem:
329766555
NACRES:
NA.22

82,80 €

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Livello qualitativo

100

Stato

solid

Impiego in reazioni chimiche

reaction type: click chemistry
reagent type: cross-linking reagent

Punto di fusione

149-157 (decomposition)

Gruppo funzionale

NHS ester

Temperatura di conservazione

−20°C

Stringa SMILE

O=C(CCC(ON(C(CC1)=O)C1=O)=O)N2CC3=C(C=CC=C3)C#CC4=C2C=CC=C4

InChI

1S/C23H18N2O5/c26-20(13-14-23(29)30-25-21(27)11-12-22(25)28)24-15-18-7-2-1-5-16(18)9-10-17-6-3-4-8-19(17)24/h1-8H,11-15H2
XCEBOJWFQSQZKR-UHFFFAOYSA-N

Categorie correlate

Descrizione generale

DBCO-NHS ester is commonly used in bioconjugation. It consists of an NHS ester that reacts with primary amines on biomolecules and an alkyne group that allows for a specific reaction with molecules containing azides. This reaction is carried out through a copper-free click chemistry process called strain-promoted alkyne-azide cycloaddition.[1]

Applicazioni

Dibenzocyclooctyne-N-hydroxysuccinimidyl ester is commonly used:
  • In the modification and labeling of biomolecules such as antibodies and streptavidin by introducing DBCO groups onto their surfaces[2]
  • As a cross linker to conjugate peptide antigens onto the surface of poly(lactic-co-glycolic acid) (PLGA) nanoparticles[3]

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
MKCW7467
MKCV7905
MKCV7904
MKCV4188
MKCT0153

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Preparation of single-and double-oligonucleotide antibody conjugates and their application for protein analytics
J Wiener, et al.
Scientific reports, 10, 1457-1457 (2020)
Nanoparticles functionalized with collagenase exhibit improved tumor accumulation in a murine xenograft model.
Murty S, et al.
Particle & Particle Systems Characterization, 31(12), 1307-1312 (2014)
Hao Ma et al.
Biomaterials, 255, 120205-120205 (2020-06-24)
Three biorthogonal click reactions, a photoinitiated thiol-yne reaction, an azide-alkyne cycloaddition, and a methyltetrazine-transcyclooctene Diels Alder, were used to independently control the presentation of several bioactive proteins to valvular interstitial cells (VICs) in hydrogel scaffolds. Tethered fibroblast growth factor (FGF-2)
Investigating functional DNA grafted on nanodiamond surface using site-directed spin labeling and electron paramagnetic resonance spectroscopy.
Akiel RD., et al.
The Journal of Physical Chemistry B, 120(17), 4003-4008 (2016)
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Nature communications, 11(1), 3244-3244 (2020-06-28)
Bioorthogonal chemistry introduces affinity-labels into biomolecules with minimal disruption to the original system and is widely applicable in a range of contexts. In proteomics, immobilized metal affinity chromatography (IMAC) enables enrichment of phosphopeptides with extreme sensitivity and selectivity. Here, we
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