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761524

Sigma-Aldrich

Dibenzocyclooctyne-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Synonyme(s) :

DBCO-NHS ester, DBCO-SE

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About This Item

Formule empirique (notation de Hill) :
C23H18N2O5
Poids moléculaire :
402.40
Numéro MDL:
MFCD24386367
Code UNSPSC :
12352108
ID de substance PubChem :
329766555
Nomenclature NACRES :
NA.22

96.50 CHF

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Devis pour commande en gros

Niveau de qualité

100

Forme

solid

Capacité de réaction

reaction type: click chemistry

Pertinence de la réaction

reagent type: cross-linking reagent

Pf

149-157 (decomposition)

Groupe fonctionnel

NHS ester

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

XCEBOJWFQSQZKR-UHFFFAOYSA-N

Catégories apparentées

Description générale

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]

Application

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]

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
MKCX5454
MKCX3186
MKCW7467
MKCV7905
MKCV7904

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Polymeric coating of silica microspheres for biological applications: suppression of non-specific binding and functionalization with biomolecules
D Brambilla, et al.
Polymers, 14, 730-730 (2022)
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)
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)
Vaccination with nanoparticles combined with micro-adjuvants protects against cancer
MO Mohsen, et al.
Journal for Immunotherapy of Cancer, 7, 1-12 (2019)
Afficher tous les articles scientifiques apparentés

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.

Click Chemistry in Drug Discovery

Explore the principles and applications of click chemistry in drug discovery, highlighting efficient reactions that streamline the synthesis of bioactive compounds.

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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