1027338-06-2

Usage

Uses

Used in Bioconjugation Applications:
3-Hydroxy-1,2:5,6-Dibenzocyclooct-7-yne is used as a bioconjugation agent for the selective and efficient ligation of biomolecules. Its unique reactivity allows for the copper-free, strain-promoted alkyne-azide cycloaddition reaction with azide-containing molecules, facilitating the formation of stable triazole linkages without the need for external catalysts.
Used in Chemical Biology Research:
In the field of chemical biology, 3-Hydroxy-1,2:5,6-Dibenzocyclooct-7-yne serves as a key component in the development of innovative imaging probes, drug delivery systems, and biomolecular labeling techniques. Its ability to react with azide-containing molecules makes it an ideal candidate for the study of cellular processes and the development of targeted therapies.
Used in Bioorthogonal Chemistry:
3-Hydroxy-1,2:5,6-Dibenzocyclooct-7-yne is utilized as a bioorthogonal reactant for the selective labeling and manipulation of biomolecules within living systems. Its high reactivity and stability enable the investigation of biological processes without disrupting native biochemical reactions, providing a powerful tool for researchers in the life sciences.
Used in Drug Delivery Systems:
3-Hydroxy-1,2:5,6-Dibenzocyclooct-7-yne is employed as a component in drug delivery systems, where its reactivity with azide-containing molecules allows for the targeted delivery of therapeutic agents to specific cells or tissues. This selective targeting can improve the efficacy and reduce the side effects of various treatments.
Used in Imaging Probe Development:
In the development of imaging probes, 3-Hydroxy-1,2:5,6-Dibenzocyclooct-7-yne is used as a reactive handle for the attachment of imaging agents, such as fluorescent dyes or radioactive isotopes, to biomolecules. This allows for the visualization and tracking of biological processes in real-time, providing valuable insights into disease mechanisms and therapeutic responses.

Upstream product

• 1192262-20-6 C₂₂H₂₆OSi 
• 1144-71-4 3-hydroxy-1,2:5,6-dibenzocycloocta-1,5,7-triene 
• 77733-39-2 5,6,11,12-tetrahydro-5,11-epoxydibenzocyclooctene 
• 122-78-1 phenylacetaldehyde 
• 3111-86-2 5-oxo-5,6-dihydrodibenzocyclooctene 
• 1144-71-4 3-hydroxy-1,2:5,6-dibenzocycloocta-1,5,7-triene 
• 2222-33-5 dibenzosuberenon 
• 3111-86-2 6H-dibenzo[a,e]cyclooctatrien-5-one 
• 1027338-07-3 3-tert-butyl-dimethylsilyl-oxy-1,2:5,6-dibenzocycloocta-1,5,7-triene 
• 1027338-08-4 11,12-dibromo-5,6,11,12-tetrahydrodibenzo[a,e]cycloocten-5-ol 

Downstream Products

• 1027338-13-1 C₃₀H₃₀N₄O₅ 
• 1027338-09-5 11,12-didehydro-5,6-dihydrodibenzo[a,e]cycloocten-5-yl carbonic acid 4-nitrophenyl ester 
• 1253203-66-5 1-benzyl-8,9-dihydro-1H-dibenzo[3,4:7,8]cycloocta[1,2-d][1,2,3]triazol-8-ol 
• 1228462-14-3 N-benzyl-8-hydroxy-2-methyl-2,3,8,9-tetrahydrodibenzo[3,4:7,8]cycloocta[1,2-d]isoxazole-3-carboxamide 
• 1228462-06-3 C₄₅H₅₈N₁₀O₁₀ 
• 1228462-09-6 2-methyl-3-phenyl-2,3,8,9-tetrahydrodibenzo[3,4:7,8]cycloocta[1,2-d]isoxazol-8-ol 
• 1262209-92-6 2-methyl-3-phenyl-2,3,8,9-tetrahydrodibenzo[3,4:7,8]cycloocta[1,2-d]isoxazol-9-ol 
• 1228462-11-0 2,3-diphenyl-2,3,8,9-tetrahydrodibenzo[3,4:7,8]cycloocta[1,2-d]isoxazol-8-ol 
• 1228462-10-9 2-methyl-3-phenethyl-2,3,8,9-tetrahydrodibenzo[3,4:7,8]cycloocta[1,2-d]isoxazol-8-ol 
• 1262209-89-1 3-(4-fluorophenyl)-8,9-dihydrodibenzo[3,4:7,8]cycloocta[1,2-d]isoxazol-9-ol 
• 1262209-94-8 3-(2-toluyl)-8,9-dihydrodibenzo[3,4:7,8]cycloocta[1,2-d]isoxazol-9-ol 
• 1262209-95-9 3-(2-phenylethyl)-8,9-dihydrodibenzo[3,4:7,8]cycloocta[1,2-d]isoxazol-9-ol 
• 1262209-86-8 3-phenyl-8,9-dihydrodibenzo[3,4:7,8]cycloocta[1,2-d]isoxazol-9-ol 
• 1262209-88-0 3-(4-nitrophenyl)-8,9-dihydrodibenzo[3,4:7,8]cycloocta[1,2-d]isoxazol-9-ol 

Relevant academic research and scientific papers

Site-specific conjugation of ScFvs antibodies to nanoparticles by bioorthogonal strain-promoted alkyne-nitrone cycloaddition

Particularly suitable: An N-terminal serine mutant of anti-HER2 scFv antibody was conjugated to polymer-coated magnetofluorescent nanoparticles by strain-promoted alkyne-nitrone cycloaddition. The resulting nanoparticles (see scheme) proved effective in t

Synthesis of 11,12-didehydrodibenzo[a,e]cycloocten-5(6H)-one: A strained eight-membered alkyne

An eight-step synthesis of 11,12-didehydrodibenzo[ a,e]cycloocten-5(6H)-one (10) was developed. The structure of 10 was assigned by spectroscopic means and confirmed by X-ray analysis of its 2,4-dinitrophenylhydrazone derivative. Reaction of the triple bond of 10 with dicarbonyl(h5-cyclopentadienyl)cobalt or dicarbonyl(η5-pentamethylcyclopentadienyl)cobalt gave the corresponding metal-stabilized cyclobutadiene complexes. Georg Thieme Verlag Stuttgart.

Bioorthogonal "labeling after Recognition" Affording an FRET-Based Luminescent Probe for Detecting and Imaging Caspase-3 via Photoluminescence Lifetime Imaging

Bis-labeling with a luminescent energy donor/acceptor pair onto biological substrates affords probes which give FRET readouts for the detection of interaction partners. However, the covalently bound luminophores bring about steric hindrance and nonspecific interaction, which probably perturb the biological recognition. Herein, we designed a highly sensitive and specific "labeling after recognition" sensing approach, where luminophore labeling occurred after the biological recognition. Taking the cutting enzyme caspase-3 as an example, we demonstrated the detection of its catalytic activity in solution and apoptotic cells using the tetrapeptide motif Asp-Glu-Val-Asp (DEVD) as the cleavable substrate, and an iridium(III) complex and a rhodamine derivative as the energy donor/acceptor pair. The DEVD tetrapeptide was modified with an azide and a GK-norbornylene groups at the amino and carboxyl terminuses, respectively, which allowed donor/acceptor bis-labeling via two independent catalysis-free bioorthogonal reactions. The phosphorescence lifetime of the iridium(III) complex was quenched upon bis-labeling owing to the intracellular FRET to the rhodamine derivative, and significantly elongated upon the peptide being catalytically cleaved by caspase-3. Interestingly, the sensitivity and efficiency of the lifetime responses were much higher in the "labeling after recognition" sensing approach. Molecular docking analysis showed that the steric hindrance and nonspecific interactions partially inhibited the biological recognition of the DEVD substrate by caspase-3. The imaging of the catalytic activity of caspase-3 in apoptotic cells was demonstrated via photoluminescence lifetime imaging microscopy. Lifetime analysis not only confirmed the occurrence of intracellular bioorthogonal bis-labeling and catalytic cleavage, but also showed the extent to which the two dynamic processes occurred.

Post-assembly derivatization of electrospun nanofibers via strain-promoted azide alkyne cycloaddition

A primary amine-derivatized 4-dibenzocyclooctynol (DIBO) was used to initiate the ring-opening polymerization of poly(γ-benzyl-l-glutamate) (DIBO-PBLG). This initiator yields well-defined PBLG polymers functionalized with DIBO at the chain termini. The DI

ALKYNES AND METHODS OF REACTING ALKYNES WITH 1,3-DIPOLE-FUNCTIONAL COMPOUNDS

1,3-Dipole-functional compounds (e.g., azide functional compounds) can be reacted with certain alkynes in a cyclization reaction to form heterocyclic compounds. Useful alkynes (e.g., strained, cyclic alkynes) and methods of making such alkynes are also di

Monomers and oligonucleotides comprising cycloaddition adduct(s)

The invention features compounds of formula (V) or (XII). In one embodiment, the invention relates compounds and processes for conjugating ligand to oligonucleotide. The invention further relates to methods for treating various disorders and diseases such

POLYMERIC STRUCTURES CONTAINING STRAINED CYCLOALKYNE FUNCTIONALITY FOR POST-FABRICATION AZIDEALKYNE CYCLOADDITION FUNCTIONALIZATION

A method of creating biocompatible polymeric structures includes the steps of: providing a biocompatible polymer including a strained cycloalkyne end group; forming a polymeric structure from the biocompatible polymer such that the strained cycloalkyne en

STRAIN-PROMOTED CROSSLINKING OF PEG-BASED HYDROGELS VIA COPPER-FREE CYCLOADDITION

The present invention is directed to a covalently crosslinked hydrogel comprising the strain-promoted reaction product of an 8-member cycloalkyne functionalized polyalkylene glycol and a multi-arm glycerol exytholate triazide and methods for making them.

Strain-Promoted Alkyne-Azide Cycloadditions (SPAAC) Reveal New Features of Glycoconjugate Biosynthesis

We have shown that 4-dibenzocyclooctynol (DIBO), which can easily be obtained by a streamlined synthesis approach, reacts exceptionally fast in the absence of a CuI catalyst with azido-containing compounds to give stable triazoles. Chemical mod

Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast huisgen cycloadditions

(Chemical Presented) CuI-free click: 4-Dibenzocyclooctynol reacts, in the absence of a CuI catalyst, exceptionally fast with azido-containing saccharides and amino acids to give stable triazoles. A biotin-modified derivative is ideal