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760676

Sigma-Aldrich

Dibenzocyclooctyne-PEG4-maleimide

for Copper-free Click Chemistry

Synonym(s):

Polyethylene glycol, DBCO-PEG4-maleimide

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About This Item

Empirical Formula (Hill Notation):
C36H42N4O9
Molecular Weight:
674.74
MDL number:
MFCD22572659
UNSPSC Code:
12161502
PubChem Substance ID:
329766888
NACRES:
NA.22

form

solid

reaction suitability

reaction type: click chemistry
reagent type: cross-linking reagent

functional group

maleimide

storage temp.

−20°C

SMILES string

O=C(CCNC(CCOCCOCCOCCOCCNC(CCN1C(C=CC1=O)=O)=O)=O)N2CC3=C(C=CC=C3)C#CC4=C2C=CC=C4

InChI

1S/C36H42N4O9/c41-32(14-18-39-34(43)11-12-35(39)44)38-17-20-47-22-24-49-26-25-48-23-21-46-19-15-33(42)37-16-13-36(45)40-27-30-7-2-1-5-28(30)9-10-29-6-3-4-8-31(29)40/h1-8,11-12H,13-27H2,(H,37,42)(H,38,41)

InChI key

VVFZXPZWVJMYPX-UHFFFAOYSA-N

Application

Maleimide functionalized cyclooctyne derivative for incorporation of the cyclooctyne moiety into thiol 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. The PEG lipophilic spacer helps to reduce aggregation and precipitation problems when labeling biomolecules.
Applications Include:
  • Protein-peptide conjugates
  • Antibody-enzyme or antibody-drug conjugates
  • Protein or peptide-oligonucleotide conjugates
  • Surface modification

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Ning, X., et al.
Angewandte Chemie (International Edition in English), 47, 2253-2255 null
Nano-scale alignment of proteins on a flexible DNA backbone.
Nojima T, et al.
PLoS ONE, 7(12), e52534-e52534 (2012)
Efficient cargo delivery into adult brain tissue using short cell-penetrating peptides
Kizil C, et al.
PLoS ONE, 10(4), e0124073-e0124073 (2015)
Xiaowen Liu et al.
Biomacromolecules, 17(1), 173-182 (2015-12-15)
Intracellularly-acting therapeutic proteins are considered promising alternatives for the treatment of various diseases. Major limitations of their application are low efficiency of intracellular delivery and possible reduction of protein activity during derivatization. Herein, we report pH-sensitive covalent modification of proteins
Lutz Nuhn et al.
Bioconjugate chemistry, 29(7), 2394-2405 (2018-06-12)
Tumor-associated macrophages (TAMs) with high expression levels of the Macrophage Mannose Receptor (MMR, CD206) exhibit a strong angiogenic and immune suppressive activity. Thus, they are a highly attractive target in cancer immunotherapy, with the aim to modulate their protumoral behavior.
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