Name: DBCO-acid
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Synonyms

11,12-Didehydro-gamma-oxodibenz[b,f]azocine-5(6H)-butanoic acid

IUPAC Name

Canonical SMILES

C1C2=CC=CC=C2C#CC3=CC=CC=C3N1C(=O)CCC(=O)O

InChI

InChI=1S/C19H15NO3/c21-18(11-12-19(22)23)20-13-16-7-2-1-5-14(16)9-10-15-6-3-4-8-17(15)20/h1-8H,11-13H2,(H,22,23)

InChIKey

NDLOVDOICXITOK-UHFFFAOYSA-N

Solubility

10 mm in DMSO

Melting Point

179.0 to 183.0 °C

PSA

57.61000

Appearance

Solid

Shipping

-20°C (International: -20°C)

Storage

Store at -20 °C, keep in dry and avoid sunlight.

Signal Word

Warning

Form

Solid

Biological Activity

DBCO-acid is a cleavable ADC linker used in the synthesis of ADC linker DBCO-NHS ester (HY-115524 and HY-115545), and druglinker conjugates DBCO-PEG-MMAE (HY-111012 and HY-126690)[1] .

DBCO-acid, a versatile chemical reagent for click chemistry applications, facilitates bioorthogonal conjugation seamlessly within biological systems. Here are four key applications of DBCO-acid:

Bioconjugation: Widely utilized for labeling biomolecules like proteins, peptides, and nucleic acids with diverse probes and tags, DBCO-acid enables the formation of stable covalent bonds through strain-promoted azide-alkyne cycloaddition (SPAAC) reactions. This precise method allows for the creation of well-defined conjugates crucial for imaging, diagnostics, and therapeutic interventions.

Drug Delivery: Within targeted drug delivery, DBCO-acid plays a pivotal role in attaching therapeutic compounds to specific targeting moieties such as antibodies or peptides. By conjugating drugs to these molecules, it enables site-specific delivery, enhancing therapeutic efficacy while minimizing off-target effects.

Surface Functionalization: In the realm of biomaterials and nanoparticles, DBCO-acid can be harnessed for surface functionalization in various biomedical applications. By modifying surfaces with DBCO groups, researchers can anchor azide-functionalized biomolecules, creating a versatile platform for applications like biosensors, tissue engineering, and regenerative medicine. This technique ensures precise and stable attachment of functional groups to the surface, enabling tailored applications.

Molecular Probes: Playing a pivotal role in designing molecular probes for biological assays and imaging studies, DBCO-acid facilitates the conjugation of fluorescent dyes or biotin to azide-functionalized molecules via DBCO chemistry. This approach allows researchers to monitor and track biological processes in real time, essential for studying cellular mechanisms, drug interactions, and biomolecular dynamics across diverse biological systems.

1. Rate determination of azide click reactions onto alkyne polymer brush scaffolds: a comparison of conventional and catalyst-free cycloadditions for tunable surface modification

Sara V Orski, Gareth R Sheppard, Selvanathan Arumugam, Rachelle M Arnold, Vladimir V Popik, Jason Locklin Langmuir. 2012 Oct 16;28(41):14693-702. doi: 10.1021/la3032418. Epub 2012 Oct 5.

The postpolymerization functionalization of poly(N-hydroxysuccinimide 4-vinylbenzoate) brushes with reactive alkynes that differ in relative rates of activity of alkyne-azide cycloaddition reactions is described. The alkyne-derived polymer brushes undergo "click"-type cycloadditions with azido-containing compounds by two mechanisms: a strain-promoted alkyne-azide cycloaddition (SPAAC) with dibenzocyclooctyne (DIBO) and azadibenzocyclooctyne (ADIBO) or a copper-catalyzed alkyne-azide cycloaddition (CuAAC) to a propargyl group (PPG). Using a pseudo-first-order limited rate equation, rate constants for DIBO, ADIBO, and PPG-derivatized polymer brushes functionalized with an azide-functionalized dye were calculated as 7.7 × 10(-4), 4.4 × 10(-3), and 2.0 × 10(-2) s(-1), respectively. The SPAAC click reactions of the surface bound layers were determined to be slower than the equivalent reactions in solution, but the relative ratio of the reaction rates for the DIBO and ADIBO SPAAC reactions was consistent between solution and the polymer layer. The rate of functionalization was not influenced by the diffusion of azide into the polymer scaffold as long as the concentration of azide in solution was sufficiently high. The PPG functionalization by CuAAC had an extremely fast rate, which was comparable to other surface click reaction rates. Preliminary studies of dilute solution azide functionalization indicate that the diffusion-limited regime of brush functionalization impacts a 50 nm polymer brush layer and decreases the pseudo-first-order rate by a constant diffusion-limited factor of 0.233.

2. Evaluation of click chemistry microarrays for immunosensing of alpha-fetoprotein (AFP)

Seyed Mohammad Mahdi Dadfar, Sylwia Sekula-Neuner, Vanessa Trouillet, Hui-Yu Liu, Ravi Kumar, Annie K Powell, Michael Hirtz Beilstein J Nanotechnol. 2019 Dec 16;10:2505-2515. doi: 10.3762/bjnano.10.241. eCollection 2019.

The level of cancer biomarkers in cells, tissues or body fluids can be used for the prediction of the presence of cancer or can even indicate the stage of the disease. Alpha-fetoprotein (AFP) is the most commonly used biomarker for early screening and diagnosis of hepatocellular carcinoma (HCC). Here, a combination of three techniques (click chemistry, the biotin-streptavidin-biotin sandwich strategy and the use of antigen-antibody interactions) were combined to implement a sensitive fluorescent immunosensor for AFP detection. Three types of functionalized glasses (dibenzocyclooctyne- (DBCO-), thiol- and epoxy-terminated surfaces) were biotinylated by employing the respective adequate click chemistry counterparts (biotin-thiol or biotin-azide for the first class, biotin-maleimide or biotin-DBCO for the second class and biotin-amine or biotin-thiol for the third class). The anti-AFP antibody was immobilized on the surfaces via a biotin-streptavidin-biotin sandwich technique. To evaluate the sensing performance of the differently prepared surfaces, fluorescently labeled AFP was spotted onto them via microchannel cantilever spotting (µCS). Based on the fluorescence measurements, the optimal microarray design was found and its sensitivity was determined.

3. Surface functionalization using catalyst-free azide-alkyne cycloaddition

Alexander Kuzmin, Andrei Poloukhtine, Margreet A Wolfert, Vladimir V Popik Bioconjug Chem. 2010 Nov 17;21(11):2076-85. doi: 10.1021/bc100306u. Epub 2010 Oct 21.

The utility of catalyst-free azide-alkyne [3 + 2] cycloaddition for the immobilization of a variety of molecules onto a solid surface and microbeads was demonstrated. In this process, the surfaces are derivatized with aza-dibenzocyclooctyne (ADIBO) for the immobilization of azide-tagged substrates via a copper-free click reaction. Alternatively, ADIBO-conjugated molecules are anchored to the azide-derivatized surface. Both immobilization techniques work well in aqueous solutions and show excellent kinetics under ambient conditions. We report an efficient synthesis of aza-dibenzocyclooctyne (ADIBO), thus far the most reactive cyclooctyne in cycloaddition to azides. We also describe convenient methods for the conjugation of ADIBO with a variety of molecules directly or via a PEG linker.