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762040

Sigma-Aldrich

Dibenzocyclooctyne-sulfo-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Sinonimo/i:

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

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1 MG
CHF 40.10
5 MG
CHF 141.00
50 MG
CHF 433.00

CHF 40.10


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1 MG
CHF 40.10
5 MG
CHF 141.00
50 MG
CHF 433.00

About This Item

Formula empirica (notazione di Hill):
C25H21N2NaO8S
Peso molecolare:
532.50
Numero MDL:
Codice UNSPSC:
12352108
ID PubChem:
NACRES:
NA.22

CHF 40.10


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Livello qualitativo

Saggio

≥90.0 %

Stato

solid

Impiego in reazioni chimiche

reaction type: click chemistry
reagent type: linker

P. ebollizione

30 -100 °C

Punto di fusione

240-260 °C

Solubilità

water: soluble at 20 °C

Temperatura di conservazione

−20°C

Stringa SMILE

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
QXKHPYSXPCJSPR-UHFFFAOYSA-M

Applicazioni

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.[1]

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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Instructing cells with programmable peptide DNA hybrids.
Freeman R, et al.
Nature Communications, 8 (2017)
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
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)

Articoli

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.

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

Questions

1–3 of 3 Questions  
  1. how stable would be a 10 mM stock in PBS/Water? Thank you

    1 answer
    1. The stability of this product in a 10 mM stock solution in PBS/water has not been tested. It is advisable to conduct preliminary stability assessments before further use.

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

    1 answer
    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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  3. 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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