
BDP 558/568 maleimide
| Catalog Number | F01-0241 |
| Category | BODIPY |
| Molecular Formula | C22H19N4BF2O3S |
| Molecular Weight | 468.28 |
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Product Introduction
BDP 558/568 is a fluorophore with a fluorescence maximum at 569 nm (in the yellow spectrum range). This dye has a low Stokes shift, high quantum yield; it is hydrophobic and relatively non-sensitive to pH changes or solvent polarity. By its spectral characteristics, BDP 558/568 is an analog of such fluorophores as BODIPY™ 558/568 and Cy3™. BDP 558/568 maleimide can be used for conjugation with peptides, proteins, antibodies, or other molecules that contain free thiol groups (-SH).
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)-N-[2-(2,5-dioxopyrrol-1-yl)ethyl]propanamide |
| SMILES | [B-]1(N2C(=CC=C2CCC(=O)NCCN3C(=O)C=CC3=O)C=C4[N+]1=C(C=C4)C5=CC=CS5)(F)F |
| InChI | InChI=1S/C22H19BF2N4O3S/c24-23(25)28-15(6-8-20(30)26-11-12-27-21(31)9-10-22(27)32)3-4-16(28)14-17-5-7-18(29(17)23)19-2-1-13-33-19/h1-5,7,9-10,13-14H,6,8,11-12H2,(H,26,30) |
| InChIKey | PDTULTXNNBHHHG-UHFFFAOYSA-N |
| Solubility | Very soluble in DMF, DMSO |
| Appearance | Dark green powder |
Product Specification
| CF260 | 0.00 |
| CF280 | 0.07 |
| Excitation | 561 |
| Emission | 569 |
| Storage | Storage: 12 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 maleimide is a maleimide-functional fluorescent dye designed for thiol-reactive bioconjugation, enabling covalent attachment to cysteine-containing biomolecules and thiol-bearing surfaces. The BDP (borondipyrromethene) scaffold provides strong fluorescence in the orange-red spectral region, making it well suited for fluorescence labeling workflows where bright, photostable signals are advantageous. In practice, this reagent is used by chemical biology and imaging teams to build fluorescent conjugates for microscopy and quantitative fluorescence assays.
1. Biomolecule Thiol Labeling
BDP 558/568 maleimide is used to fluorescently label proteins, peptides, and other cysteine- or thiol-containing reagents through rapid maleimide-thiol coupling, supporting downstream fluorescence imaging and quantification. Researchers commonly incorporate the dye into antibody fragments, enzyme reagents, affinity ligands, and protein standards to generate defined fluorescent conjugates for binding studies, localization experiments, and assay development. The orange-red emission profile helps separate labeled targets from common background autofluorescence in many biological sample types, supporting clear visualization in fluorescence microscopy and plate-based readouts.
2. Fluorescent Probe Construction
BDP 558/568 maleimide is frequently employed as a labeling handle during fluorescent probe development, where a thiol-reactive fluorophore is needed to create targeted or modular imaging reagents. In chemical biology workflows, the dye is conjugated to recognition elements such as cysteine-bearing peptides, engineered binding proteins, or oligonucleotide-linked thiols to produce fluorescent molecular imaging tools. Teams developing probe libraries for screening and mechanistic studies use the maleimide functionality to attach the fluorophore at controlled sites, enabling consistent probe performance across experiments and facilitating comparative imaging of probe uptake, binding, or transport.
3. Surface And Material Functionalization
BDP 558/568 maleimide supports fluorescence-enabled biomaterials and surface engineering by enabling covalent dye immobilization on thiol-functionalized polymers, nanoparticles, and hydrogel matrices. Materials scientists and imaging groups use the reagent to create fluorescently labeled surfaces for tracking material interactions, monitoring surface-mediated binding events, and validating surface modification steps. By anchoring the dye via thiol-reactive chemistry, the resulting fluorescent materials are useful for microscopy-based localization and for quantitative fluorescence measurements that report on surface coverage, coating uniformity, or material association in complex experimental systems.
4. Flow Cytometry Labeling
BDP 558/568 maleimide is applied in flow cytometry workflows that require fluorescent labeling of thiol-containing biomolecules for cell-associated readouts. Researchers use maleimide conjugation to attach the dye to cysteine-bearing ligands or to thiol-modified targeting constructs, enabling fluorescence detection of labeled binding events on cell surfaces or in cell-associated assays. The BDP 558/568 emission region is leveraged to select appropriate detector channels and to support multiplexing strategies where separation from other fluorophores is required, improving interpretability of fluorescence signals in quantitative cytometry experiments.
Computed Properties
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 7 |
| Exact Mass | 468.1238981 g/mol |
| Monoisotopic Mass | 468.1238981 g/mol |
| Topological Polar Surface Area | 103Ų |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Complexity | 994 |
| 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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