
BDP 558/568 hydrazide
| Catalog Number | R05-0001 |
| Category | BODIPY |
| Molecular Formula | C16H16N4BClF2OS |
| Molecular Weight | 396.65 |
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Product Introduction
Carbonyl groups of aldehyde/ketone type are very often found in natural and synthetic molecules. Aldehydes and ketones can be efficiently labeled with hydrazides with the formation of stable hydrazones. This compound is a carbonyl reactive hydrazide derivative of BDP 558/568 dye which has its emission in yellow range of the spectrum.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| Purity | NMR 1H, HPLC-MS (95%) |
| IUPAC Name | [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)propanoylamino]azanium;chloride |
| SMILES | [B-]1(N2C(=CC=C2CCC(=O)N[NH3+])C=C3[N+]1=C(C=C3)C4=CC=CS4)(F)F.[Cl-] |
| InChI | InChI=1S/C16H15BF2N4OS.ClH/c18-17(19)22-11(6-8-16(24)21-20)3-4-12(22)10-13-5-7-14(23(13)17)15-2-1-9-25-15;/h1-5,7,9-10H,6,8,20H2,(H,21,24);1H |
| InChIKey | XNJDXKAVOZGJNT-UHFFFAOYSA-N |
| Solubility | good in DMF, DMSO |
| 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 hydrazide is a reactive fluorescent hydrazide designed for covalent labeling of carbonyl-containing biomolecules, enabling stable attachment of a bright BODIPY fluorophore in fluorescence microscopy and fluorescence imaging workflows. The dye's excitation/emission in the yellow-orange to red spectral window supports multicolor experiments where BODIPY brightness and photostability are advantageous, while the hydrazide functionality is used to generate conjugates with aldehyde- or ketone-bearing targets for downstream imaging and assay development.
1. Fluorescent Protein Labeling
BDP 558/568 hydrazide is used by protein chemistry and chemical biology groups to prepare fluorescent protein conjugates for imaging and binding studies. In practical workflows, researchers introduce carbonyl handles to proteins (for example, via oxidation strategies) and then use the hydrazide to form a covalent fluorescent adduct, producing labeling reagents that are compatible with standard fluorescence microscopes and plate-based fluorescence readers. This approach is commonly applied when stable labeling is preferred over passive adsorption, and when a BODIPY dye in the 558/568 region provides strong signal for tracking biomolecular localization.
2. Microscopy Imaging Probes
BDP 558/568 hydrazide is frequently incorporated into microscopy probe development for visualizing labeled biomolecules in fixed-cell or fixed-sample fluorescence experiments. By converting carbonyl-containing biomolecules into covalently labeled fluorescent constructs, researchers generate imaging reagents used to map distributions of targets such as extracellular components, immobilized biomolecular layers, or labeled affinity reagents on surfaces. The hydrazide-driven conjugation strategy is especially useful in molecular staining and imaging reagent pipelines where consistent covalent attachment improves wash resistance during microscopy sample preparation.
3. Biomaterial Surface Functionalization
BDP 558/568 hydrazide is used in biomaterials and surface engineering to create fluorescently tagged coatings and functional layers for materials characterization and imaging-based quality control. After introducing carbonyl functionalities onto polymers, hydrogels, or surface-modified materials, the hydrazide dye is applied to generate fluorescent surfaces that can be imaged to assess coating uniformity, immobilization efficiency, or spatial patterning. This labeling route is also leveraged for building fluorescently readable materials in assay development, where the labeled surface serves as a platform for monitoring binding events or reagent immobilization.
4. Fluorescence-Based Bioassay Development
BDP 558/568 hydrazide supports fluorescence assay development by enabling preparation of fluorescent conjugates used as reporters in binding and detection assays. Researchers use hydrazide labeling to attach the BODIPY fluorophore to carbonyl-bearing assay components, producing fluorescent reagents for plate reader measurements and workflow-compatible imaging readouts. In assay development contexts, the 558/568 spectral region helps align the reporter with common filter sets while the covalent labeling strategy helps maintain reagent integrity across incubation and wash steps.
Computed Properties
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 4 |
| Exact Mass | 396.0794465 g/mol |
| Monoisotopic Mass | 396.0794465 g/mol |
| Topological Polar Surface Area | 92.9Ų |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Complexity | 681 |
| 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 | 2 |
| Compound Is Canonicalized | Yes |
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