
BDP 581/591 alkyne | CAS 2006345-34-0
| Catalog Number | R02-0014 |
| Category | Alkynes |
| Molecular Formula | C25H22N3BF2O |
| Molecular Weight | 429.27 |
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Product Introduction
BDP 581/591 is a borondipyrromethene fluorophore that is moderately hydrophobic. It is useful for fluorescence polarization assays, and microscopy. Due to its significant two photon absorption cross section, the dye is also useful for two photon experiments. This is a terminal alkyne for copper-catalyzed Click chemistry.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| Synonyms | BDP581/591alkyne |
| Purity | NMR 1H, HPLC-MS (95%) |
| IUPAC Name | 3-[2,2-difluoro-12-[(1E,3E)-4-phenylbuta-1,3-dienyl]-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaen-4-yl]-N-prop-2-ynylpropanamide |
| SMILES | [B-]1(N2C(=CC=C2CCC(=O)NCC#C)C=C3[N+]1=C(C=C3)C=CC=CC4=CC=CC=C4)(F)F |
| InChI | InChI=1S/C25H22BF2N3O/c1-2-18-29-25(32)17-16-22-13-15-24-19-23-14-12-21(30(23)26(27,28)31(22)24)11-7-6-10-20-8-4-3-5-9-20/h1,3-15,19H,16-18H2,(H,29,32)/b10-6+,11-7+ |
| InChIKey | OLFSHALJABVHGP-JMQWPVDRSA-N |
| Solubility | good in DCM, DMF, DMSO |
| Appearance | dark colored solid |
Product Specification
| ε, L⋅mol-1⋅cm-1 | 104000 |
| Fluorescence Quantum Yield | 0.83 |
| Excitation | 585 |
| Emission | 594 |
Application
BDP 581/591 alkyne is an alkyne-functionalized BODIPY fluorophore designed for click chemistry labeling workflows where bright, photostable fluorescence is required. Its reactive alkyne handle enables efficient conjugation to azide-bearing biomolecules, linkers, and surfaces, supporting fluorescent probe construction, biomolecule tracking, and assay reagent development in fluorescence microscopy and related instrumentation. The BDP 581/591 spectral positioning (green-to-orange emission region) makes it a practical dye for multicolor labeling strategies when paired with compatible far-red or green channels.
1. Biomolecule Labeling
BDP 581/591 alkyne is used by chemical biology and fluorescence imaging groups to label proteins, peptides, and other azide-functional biomolecules via copper-catalyzed azide-alkyne cycloaddition or strain-promoted click formats (depending on the azide partner). Researchers incorporate the resulting BODIPY conjugates into labeling panels for tracking binding, uptake, or localization in fixed-cell imaging workflows and in fluorescence-based characterization of biomolecular interactions. The alkyne functionality supports modular probe assembly, including attachment to affinity reagents, targeting ligands, and assay-compatible linkers.
2. Fluorescent Probe Construction
BDP 581/591 alkyne serves as a versatile fluorophore building block for fluorescent probe development, where the alkyne group is used to install the dye onto azide-bearing scaffolds such as peptide probes, polymer backbones, or imaging reporters. Probe developers commonly use BDP 581/591 conjugates in microscopy experiments and fluorescence readouts to visualize labeled targets or to generate standardized fluorescent reagents for method development. Because the dye is directly incorporated through click-compatible handles, it is frequently selected for constructing reproducible conjugates with defined dye loading on the final probe platform.
3. Surface Functionalization
BDP 581/591 alkyne is applied in materials and biomaterials research to create fluorescently addressable surfaces and coatings by click immobilization onto azide-functional substrates. Lab teams use the dye-labeled materials to visualize material-biomolecule interactions, map adsorption or surface coverage, and generate fluorescent reference standards for microscopy studies of engineered interfaces. The alkyne handle enables straightforward coupling to surface chemistries that present azide groups, supporting workflows for nanoparticle labeling, hydrogel functionalization, and fluorescent surface patterning in research settings.
4. Fluorescence Imaging Reagents
BDP 581/591 alkyne is frequently incorporated into imaging reagent development where a stable, BODIPY-based fluorophore is needed for cellular and molecular visualization. Imaging specialists use click-assembled BDP 581/591 conjugates as labeling reagents for multicolor experiments, including experiments that require consistent fluorescence intensity across labeled samples. The alkyne functionality supports rapid exchange of targeting or binding modules by coupling to different azide-bearing ligands, enabling iterative optimization of fluorescent staining and imaging workflows for microscopy and related fluorescence instrumentation.
Computed Properties
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 7 |
| Exact Mass | 429.1823988 g/mol |
| Monoisotopic Mass | 429.1823988 g/mol |
| Topological Polar Surface Area | 37Ų |
| Heavy Atom Count | 32 |
| Formal Charge | 0 |
| Complexity | 934 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 2 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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