764019

Sigma-Aldrich

Dibenzocyclooctyne-PEG4-N-hydroxysuccinimidyl ester

95%

Synonym(s):
DBCO-PEG4-succinimidyl ester, DBCO-PEG4-NHS ester, DBCO-PEG4-SE
Empirical Formula (Hill Notation):
C34H39N3O10
Molecular Weight:
649.69
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

reaction suitability

reaction type: click chemistry

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

Related Categories

Application

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
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.

Packaging

1, 5, 50 mg in clear glass bottle

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificate of Analysis

Certificate of Origin

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...
null
PSMA?targeted SPECT agents: Mode of binding effect on in vitro performance.
Nedrow?Byers JR, et al.
Prostate, 73(4), 355-362 (2013)
Seong Ho Kim et al.
ACS nano, 11(9), 9352-9359 (2017-08-29)
Reversible regulation of enzyme activity by chemical and physical stimuli is often achieved by incorporating stimuli-responsive domains in the enzyme of interest. However, this method is suitable for a limited number of enzymes with well-defined structural and conformational changes. In...

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