
BDP 558/568 azide
| Catalog Number | F01-0002 |
| Category | BODIPY |
| Molecular Formula | C19H19N6BF2OS |
| Molecular Weight | 428.27 |
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Product Introduction
BDP 558/568 azide is a borondipyrromethene dye with azide functional group for Click chemistry. Its spectra are close to Cyanine3 channel. The fluorophore has been used for lipid tracking as BDP 558/568 C12, but azide functional groups allow easy conjugation with a wide variety of other molecules of interest.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| Synonyms | Bodipy 558/568 azide |
| Purity | NMR 1H, HPLC-MS (95%) |
| IUPAC Name | N-(3-azidopropyl)-3-(2,2-difluoro-12-thiophen-2-yl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-4-yl)propanamide |
| SMILES | [B-]1(N2C(=CC=C2CCC(=O)NCCCN=[N+]=[N-])C=C3[N+]1=C(C=C3)C4=CC=CS4)(F)F |
| InChI | InChI=1S/C19H19BF2N6OS/c21-20(22)27-14(7-9-19(29)24-10-2-11-25-26-23)4-5-15(27)13-16-6-8-17(28(16)20)18-3-1-12-30-18/h1,3-6,8,12-13H,2,7,9-11H2,(H,24,29) |
| InChIKey | ZPOKKCUBLPETSH-UHFFFAOYSA-N |
| Solubility | soluble in many organic solvents (DCM, acetone, alcohols, DMF, DMSO), low solubility in water |
| Appearance | dark colored solid |
Product Specification
| ε, L⋅mol-1⋅cm-1 | 84400 |
| Excitation | 561 |
| Emission | 569 |
| Storage | 24 months after receival at -20°C in the dark. Transportation: at room temperature for up to 3 weeks. Avoid prolonged exposure to light. Desiccate. |
Application
BDP 558/568 azide is an azide-functionalized BODIPY fluorophore designed for copper-free click chemistry workflows that couple bright, photostable dyes to biomolecules and materials. Its BDP core supports fluorescence in the 550-600 nm range, making it a practical red/orange-emitting label for fluorescence microscopy, imaging assays, and flow-based readouts when paired with appropriate excitation optics. The azide handle enables straightforward incorporation into conjugates via strain-promoted azide-alkyne cycloaddition (SPAAC) using complementary cyclooctyne/DBCO partners.
1. Biomolecule Labeling
BDP 558/568 azide is used by chemical biology and glycobiology groups to fluorescently tag proteins, peptides, and other amine-containing or thiol-containing biomolecules after they are equipped with a cyclooctyne/DBCO handle. This labeling approach is common in workflows where researchers need a stable, covalent dye conjugate for tracking biomolecule binding, uptake, or trafficking in cell-based experiments. The 558/568 emission window is frequently selected for multiplexing with other fluorophores and for imaging formats that require a red-shifted signal with reduced spectral overlap compared with green dyes.
2. Fluorescence Microscopy Imaging
BDP 558/568 azide serves as a convenient labeling reagent for fluorescence microscopy studies that visualize labeled biomolecule localization on cells, within extracellular matrices, or on engineered surfaces. In practice, researchers generate dye-biomolecule conjugates by click coupling to cyclooctyne-functional targeting ligands or biomaterials, then image the resulting constructs using standard fluorescence microscopes equipped with appropriate excitation/emission filters for the BDP 558/568 spectral region. The azide functionality supports modular probe construction, enabling rapid swapping of targeting components while keeping the same fluorophore readout.
3. Flow Cytometry Labeling
BDP 558/568 azide is applied in flow cytometry experiments where covalent fluorescent labeling of cell-associated reagents is required for quantitative population analysis. Many users prepare cyclooctyne/DBCO-bearing antibodies, ligands, or polymeric carriers and then couple them with BDP 558/568 azide to generate consistent, dye-defined conjugates for staining panels. The resulting 558/568 emission is commonly leveraged to separate signals from other channels in multicolor panels and to support reproducible fluorescence readouts for binding and uptake studies.
4. Surface Functionalization
BDP 558/568 azide is also used in biomaterials and surface engineering to create fluorescently addressable materials by click immobilization onto cyclooctyne-functional substrates. Researchers incorporate the dye into hydrogels, coatings, and nanoparticle surfaces to enable spatial mapping of material components, monitor coating uniformity, or visualize diffusion and retention in engineered microenvironments. This application benefits from the modular azide handle, which allows the same fluorophore to be attached to different material platforms using the corresponding cyclooctyne/DBCO surface chemistry.
Computed Properties
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 8 |
| Exact Mass | 428.1402169 g/mol |
| Monoisotopic Mass | 428.1402169 g/mol |
| Topological Polar Surface Area | 79.6Ų |
| Heavy Atom Count | 30 |
| Formal Charge | 0 |
| Complexity | 841 |
| 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 |
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