
DBCO-acid | CAS 1353016-70-2
| Catalog Number | R01-0285 |
| Category | Cycloalkyne Dyes (DBCO) |
| Molecular Formula | C19H15NO3 |
| Molecular Weight | 305.33 |
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Product Introduction
DBCO-acid serves as a copper-free click chemistry linker for azide-based bioconjugation. Its carboxyl group allows further derivatization, making it a key component in the design of stable and bioorthogonal ADC linkers.
Chemical Information
Product Specification
Application
Computed Properties
Patents
Chemical Information
| Synonyms | 11,12-Didehydro-gamma-oxodibenz[b,f]azocine-5(6H)-butanoic acid |
| Purity | > 98.0 % |
| IUPAC Name | |
| 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 |
| Appearance | Solid |
| Melting Point | 179.0 to 183.0 °C |
| LogP | 2.86280 |
Product Specification
| Storage | Store at -20 °C, keep in dry and avoid sunlight. |
| Signal | Warning |
| GHSHazardStatements | H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] |
| Precautionary Statement Codes | P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Application
DBCO-acid is a strained cyclooctyne building block designed for copper-free click chemistry, providing a reactive DBCO (dibenzocyclooctyne) handle that couples efficiently with azide-functional partners under mild conditions. As a carboxylic acid derivative, it is commonly used to introduce a DBCO moiety into linkers, surfaces, and biomolecule conjugates while retaining a functional group for further coupling or material attachment. This reagent is widely relevant to chemical biology workflows where stable, orthogonal conjugation is needed for probe, imaging, and materials fabrication.
1. Bioconjugation With Azides
DBCO-acid is frequently used to generate azide-reactive conjugates for research-grade labeling of biomolecules and biomolecule-derived constructs. The DBCO cyclooctyne enables copper-free strain-promoted azide–alkyne cycloaddition (SPAAC) with azide-bearing targets such as peptides, proteins, glycans, and nucleic-acid analogs, supporting workflows that benefit from avoiding copper-related effects on sensitive biomaterials. The carboxylic acid functionality also supports downstream derivatization into defined linkers, improving how conjugates are presented to cells, enzymes, or binding reagents in assay development and molecular biology toolkits.
2. Surface And Material Functionalization
DBCO-acid is commonly incorporated into surface modification strategies and polymer or hydrogel functionalization schemes where azide groups are presented on the material scaffold. Researchers use this reagent to install DBCO moieties onto coatings, nanoparticles, and macromolecular matrices so that subsequent azide-click steps can attach fluorescent tags, affinity ligands, or other functional components with minimal processing. The acid group facilitates coupling to activated surfaces or incorporation into material chemistries, making DBCO-acid a practical choice for building multicomponent materials used in imaging assays, biosensing platforms, and spatially organized chemical libraries.
3. Fluorescent Probe And Imaging Labeling
DBCO-acid is widely used as a DBCO source for preparing azide-reactive fluorescent probes and imaging reagents in chemical biology and molecular imaging research. By converting the acid into an appropriate linker format, the DBCO handle can be positioned to attach dyes, imaging reporters, or imaging-compatible tags to azide-functional biomolecules and probe scaffolds. This approach is especially useful when probe assembly must proceed under conditions compatible with labeled biomaterials, enabling modular construction of imaging reagents for microscopy, flow-based readouts, and platform screening.
4. Diagnostic Reagent Development
DBCO-acid is applied in the development of diagnostic and assay reagents that rely on modular conjugation to azide-functional capture elements, reporters, or assay components. In many research and industrial settings, DBCO-acid-derived linkers are used to prepare conjugates where a DBCO-bearing reagent can be clicked onto azide-tagged surfaces, beads, or assay reagents to assemble multiplexed detection formats. The carboxylic acid functionality supports integration into linker architectures used to control attachment geometry, which is valuable for building consistent reagent batches for assay prototyping and reagent kit workflows.
Computed Properties
| XLogP3 | 2.3 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Exact Mass | 305.10519334 g/mol |
| Monoisotopic Mass | 305.10519334 g/mol |
| Topological Polar Surface Area | 57.6Ų |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Complexity | 529 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| WO-2022263944-A1 | Azido-containing monomers, polymers, and articles | 2021-06-16 |
| WO-2022258794-A2 | A conjugate | 2021-06-09 |
| CN-113234236-A | Viscoelastic hydrogel and preparation method and application thereof | 2021-05-08 |
| CN-112957463-A | Immune activation type antibody and application thereof | 2021-02-22 |
| CN-113663067-A | Immune activation type antibody and application thereof | 2021-02-22 |
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