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Merck
CN

760676

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
NACRES:
NA.22
PubChem Substance ID:
329766888
UNSPSC Code:
12161502
MDL number:
MFCD22572659

Key Documents

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Product Name

Dibenzocyclooctyne-PEG4-maleimide, for Copper-free Click Chemistry

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)

SMILES string

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

InChI key

VVFZXPZWVJMYPX-UHFFFAOYSA-N

form

solid

reaction suitability

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

functional group

maleimide

storage temp.

−20°C

Related Categories

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV6020
MKCT3586
MKCS5655
MKCN2592
MKCR1149

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Efficient cargo delivery into adult brain tissue using short cell-penetrating peptides
Kizil C, et al.
PLoS ONE, 10(4), e0124073-e0124073 (2015)
Nano-scale alignment of proteins on a flexible DNA backbone.
Nojima T, et al.
PLoS ONE, 7(12), e52534-e52534 (2012)
Ning, X., et al.
Angewandte Chemie (International Edition in English), 47, 2253-2255 null
Nalinikanth Kotagiri et al.
Bioconjugate chemistry, 25(7), 1272-1281 (2014-06-18)
Antibody-based proteomics is an enabling technology that has significant implications for cancer biomarker discovery, diagnostic screening, prognostic and pharmacodynamic evaluation of disease state, and targeted therapeutics. Quantum dot based fluoro-immunoconjugates possess promising features toward realization of this goal such as
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
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Click Chemistry in Drug Discovery

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

Copper-Free Click Chemistry

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.

无铜点击化学

无铜点击化学是点击化学的一种替代方法，可在较低的活化屏障下进行，且没有细胞毒性过渡金属催化剂。

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