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764019

Sigma-Aldrich

Dibenzocyclooctyne-PEG4-N-hydroxysuccinimidyl ester

≥90%

Synonym(s):

DBCO-PEG4-NHS ester, DBCO-PEG4-SE, DBCO-PEG4-succinimidyl ester

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About This Item

Empirical Formula (Hill Notation):
C34H39N3O10
Molecular Weight:
649.69
MDL number:
MFCD26793797
UNSPSC Code:
12352108
PubChem Substance ID:
329767092
NACRES:
NA.22

Quality Level

100

assay

≥90%

form

paste

reaction suitability

reaction type: click chemistry
reagent type: linker

functional group

NHS ester

storage temp.

−20°C

SMILES string

O=C(CCC(NCCOCCOCCOCCOCCC(ON1C(CCC1=O)=O)=O)=O)N2CC3=C(C=CC=C3)C#CC4=C2C=CC=C4

InChI

1S/C34H39N3O10/c38-30(11-12-31(39)36-25-28-7-2-1-5-26(28)9-10-27-6-3-4-8-29(27)36)35-16-18-44-20-22-46-24-23-45-21-19-43-17-15-34(42)47-37-32(40)13-14-33(37)41/h1-8H,11-25H2,(H,35,38)

InChI key

RRCXYKNJTKJNTD-UHFFFAOYSA-N

Application

Dibenzocyclooctyne-PEG4-N-hydroxysuccinimidyl ester may be used in the synthesis of a prostate-specific membrane antigen (PSMA)-targeted single photon emission computed tomography (SPECT) agent via copper-less click chemistry.
Succinimidyl ester (NHS, amine reactive) functionalized cyclooctyne derivative for incorporation of the cyclooctyne moiety into amine containing compounds or biomolecules. Cyclooctynes are useful in strain-promoted copper-free click chemistry 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.

Applications Include:
  • Protein-peptide conjugates
  • Antibody-enzyme or antibody-drug conjugates
  • Protein or peptide-oligonucleotide conjugates
  • Surface modification

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ4602
MKCM2106
MKCM2410
MKCM2107
MKCL7020

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Huang-Chiao Huang et al.
Small (Weinheim an der Bergstrasse, Germany), e1800236-e1800236 (2018-07-03)
The past three decades have witnessed notable advances in establishing photosensitizer-antibody photo-immunoconjugates for photo-immunotherapy and imaging of tumors. Photo-immunotherapy minimizes damage to surrounding healthy tissue when using a cancer-selective photo-immunoconjugate, but requires a threshold intracellular photosensitizer concentration to be effective.
Clinton H Hansen et al.
Proceedings of the National Academy of Sciences of the United States of America, 114(39), 10367-10372 (2017-09-13)
Protein detection and quantification play critical roles in both basic research and clinical practice. Current detection platforms range from the widely used ELISA to more sophisticated, and more expensive, approaches such as digital ELISA. Despite advances, there remains a need
PSMA?targeted SPECT agents: Mode of binding effect on in vitro performance.
Nedrow?Byers JR, et al.
Prostate, 73(4), 355-362 (2013)
Matthias Krumb et al.
Cells, 9(9) (2020-09-17)
Herein, we report the synthesis of carbohydrate and glycodendron structures for dendritic cell targeting, which were subsequently bound to hydroxyethyl starch (HES) nanocapsules prepared by the inverse miniemulsion technique. The uptake of the carbohydrate-functionalized HES nanocapsules into immature human dendritic
Hong Pan et al.
Biomaterials, 181, 199-209 (2018-08-08)
Enterovirus 71 (EV71), the major pathogen of hand-foot-and-mouth disease (HFDM), can cause severe neurological and respiratory manifestations in young children. Viral spread route and tissue tropism are key factors contributing to different pathogenicity of EV71, however it remains a challenge
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