
BDP 581/591 hydrazide
| Catalog Number | R05-0002 |
| Category | BODIPY |
| Molecular Formula | C22H22N4BClF2O |
| Molecular Weight | 442.7 |
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Product Introduction
BDP 581/591 hydrazide is a carbonyl reactive dye. BDP 581/591 is a borondipyrromethene fluorophore with bright emission, and oustanding photostability.Aldehyde and ketone groups that can be labeled can be obtained by oxidation of 1,2-diol groups in sugars; they are also present in proteins after oxidative stress, and in many small molecules.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| Related CAS | 2183473-40-5 (hydrochloride) 2183473-39-2 (inner salt) |
| 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]propanoylamino]azanium;chloride |
| SMILES | [B-]1(N2C(=CC=C2CCC(=O)N[NH3+])C=C3[N+]1=C(C=C3)C=CC=CC4=CC=CC=C4)(F)F.[Cl-] |
| InChI | InChI=1S/C22H21BF2N4O.ClH/c24-23(25)28-18(9-5-4-8-17-6-2-1-3-7-17)10-12-20(28)16-21-13-11-19(29(21)23)14-15-22(30)27-26;/h1-13,16H,14-15,26H2,(H,27,30);1H/b8-4+,9-5+; |
| InChIKey | YBNBSHNGIGNNNW-VYMJFYGFSA-N |
| Solubility | good in DMF, DMSO, alcohols |
| Appearance | dark colored solid |
Product Specification
| ε, L⋅mol-1⋅cm-1 | 104000 |
| Fluorescence Quantum Yield | 0.83 |
| Excitation | 585 |
| Emission | 594 |
| 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 581/591 hydrazide is a reactive fluorescent hydrazide designed for covalent labeling of aldehyde-containing biomolecules and materials, enabling stable attachment of a bright BODIPY dye to biological targets used in fluorescence imaging workflows. In practice, it is commonly paired with aldehyde-functional handles introduced onto proteins, peptides, glycans, or polymer surfaces, providing a convenient route to fluorescent conjugates for microscopy and fluorescence-based assay development. The BDP 581/591 spectral profile (orange-red emission region) supports multicolor imaging strategies where BODIPY signal is detected on standard fluorescence microscope and plate-reader platforms.
1. Protein Aldehyde Labeling
BDP 581/591 hydrazide is frequently used by cell biology and chemical biology groups to fluorescently tag proteins that have been oxidized to introduce aldehyde groups, such as glycoproteins or carbohydrate-modified biomolecules. Researchers use the resulting BDP-labeled conjugates for cellular imaging, localization studies, and quantitative fluorescence readouts in plate-based assays where covalent attachment improves retention during washing steps. This reagent format is also used to prepare fluorescent standards for assay calibration and to generate labeled affinity reagents for downstream binding experiments.
2. Biomolecule Conjugate Preparation
BDP 581/591 hydrazide supports construction of fluorescent bioconjugates from aldehyde-functional biomolecules, including peptides, oligonucleotide conjugates, and affinity ligands that have been equipped with aldehyde handles. In molecular imaging reagent development, teams use the hydrazide to generate stable fluorescent tags for tracking binding events, reagent uptake, or distribution in complex biological mixtures. The covalent labeling approach is particularly useful when conjugates must withstand repeated buffer exchanges, imaging time courses, or assay workflows that include fixation or membrane-permeabilization steps.
3. Polymer And Surface Functionalization
BDP 581/591 hydrazide is applied in biomaterials research to fluorescently functionalize aldehyde-bearing polymers, hydrogels, and surface coatings used for imaging and characterization. Materials scientists commonly incorporate the dye into polymer networks or onto functionalized substrates to visualize surface coverage, track diffusion or adsorption behavior, and verify uniform labeling across batches. This workflow is also used to create fluorescently tagged materials for microscopy-based studies of cell-material interactions, scaffold remodeling, and spatial mapping of labeled biomaterial components.
4. Fluorescence Imaging And Microscopy
BDP 581/591 hydrazide-derived conjugates are used in fluorescence microscopy to visualize labeled biomolecules in fixed-cell and in vitro imaging experiments, leveraging the dye's orange-red emission for clear separation from common green-channel fluorophores. Imaging teams often choose this reagent when they need a covalent fluorescent label that remains associated with the target during staining, washing, and mounting. The resulting BDP-labeled constructs are also used for fluorescence intensity mapping in microscopy studies that require consistent labeling chemistry across experimental conditions.
Computed Properties
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 6 |
| Exact Mass | 442.1543255 g/mol |
| Monoisotopic Mass | 442.1543255 g/mol |
| Topological Polar Surface Area | 64.7Ų |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Complexity | 827 |
| 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 | 2 |
| Compound Is Canonicalized | Yes |
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