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762040

Sigma-Aldrich

Dibenzocyclooctyne-sulfo-N-hydroxysuccinimidyl ester

for Copper-free Click Chemistry

Synonym(s):

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

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10 G
¥1,590.46
100 G
¥9,752.37

¥1,590.46

Available to ship on2025年4月07日Details

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10 G
¥1,590.46
100 G
¥9,752.37

About This Item

Empirical Formula (Hill Notation):
C25H21N2NaO8S
Molecular Weight:
532.50
MDL number:
MFCD22572669
UNSPSC Code:
12352108
PubChem Substance ID:
329766600
NACRES:
NA.22

¥1,590.46

Available to ship on2025年4月07日Details

Request a Bulk Order

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

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

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

InChI key

QXKHPYSXPCJSPR-UHFFFAOYSA-M

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technique(s)

cell culture | embryo: suitable

technique(s)

cell culture | insect: suitable, cell culture | mammalian: suitable, cell culture | plant: suitable

technique(s)

cell culture | hybridoma: suitable

technique(s)

gas chromatography (GC): suitable

solubility

H2O: 2g + 15 mL, clear, colorless

solubility

H2O: 2g + 15 mL (Tested)

solubility

H2O: 2g + 15 mL (Tested)

solubility

H2O: 1 M

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

powder

form

powder

form

powder

form

powder

mp

150-152 °C (lit.)

mp

150-152 °C (lit.)

mp

150-152 °C (lit.)

mp

150-152 °C (lit.)

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.[1]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    MKCX2357
    MKCX1661
    MKCX2001
    MKCV9503
    MKCW6127

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    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)
    Switchable supramolecular catalysis using DNA-templated scaffolds.
    Garcia MAA, et al.
    Chemical Communications (Cambridge, England), 52(10), 2153-2156 (2016)
    Hyun Jong Lee et al.
    Advanced healthcare materials, 7(19), e1800560-e1800560 (2018-08-15)
    In this study, an in situ forming corneal stromal substitute based on collagen type I crosslinked by bio-orthogonal strain-promoted azide-alkyne cycloaddition (SPAAC) is presented. The crosslinked collagen gel has greater transparency compared to non-crosslinked collagen gels. The mechanical properties of
    Stimuli-Responsive Nucleic Acid-Functionalized Metal-Organic-Framework Nanoparticles Using pH-and Metal-Ion Dependent DNAzymes as Locks.
    Chen WH, et al.
    Chemical Science (2017)
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