
BDP 581/591 maleimide | CAS 2183473-29-0
| Catalog Number | F01-0228 |
| Category | BODIPY |
| Molecular Formula | C28H25BF2N4O3 |
| Molecular Weight | 514.3 |
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Product Introduction
BDP 581/591 maleimide is a linker of the BDP 581/591 dye. It has a long fluorescence lifetime and can be used for fluorescence polarization assays. The maleimide group can react with thiol groups to form thioester bonds between pH 6.5 to 7.5.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| Synonyms | BDP581/591maleimide |
| Purity | 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-[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)C=CC=CC5=CC=CC=C5)(F)F |
| InChI | InChI=1S/C28H25BF2N4O3/c30-29(31)34-22(9-5-4-8-21-6-2-1-3-7-21)10-12-24(34)20-25-13-11-23(35(25)29)14-15-26(36)32-18-19-33-27(37)16-17-28(33)38/h1-13,16-17,20H,14-15,18-19H2,(H,32,36)/b8-4+,9-5+ |
| InChIKey | YPTVPBNWROLSKT-KBXRYBNXSA-N |
| Solubility | DMF, DMSO, DCM |
Product Specification
| Excitation | 585 |
| Emission | 594 |
| Storage | -20 °C |
Application
BDP 581/591 maleimide is a maleimide-functionalized BODIPY dye designed for thiol-reactive fluorescent labeling. Its bright, photostable BODIPY core supports fluorescence microscopy and quantitative imaging workflows, while the maleimide handle enables conjugation to cysteine-containing biomolecules and thiol-bearing surfaces. This reagent is frequently used to build fluorescent conjugates for tracking, localization, and labeling optimization in chemical biology, biomaterials, and assay development.
1. Biomolecule Thiol Labeling
BDP 581/591 maleimide is used by chemical biology and protein chemistry groups to fluorescently label peptides, proteins, and other biomolecules that present accessible thiol groups (e.g., engineered cysteine residues or reduced cysteines). Researchers incorporate the resulting dye conjugates into binding studies, uptake and trafficking experiments, and labeling controls where a stable BODIPY fluorophore is advantageous. The maleimide chemistry supports straightforward preparation of fluorescent conjugates for downstream imaging and quantitative fluorescence readouts.
2. Fluorescent Probe Conjugates
BDP 581/591 maleimide serves as a key building block for constructing fluorescent probe conjugates used in molecular imaging and fluorescence-based assays. Teams in diagnostics reagent development and bioassay development often label targeting ligands, affinity reagents, or reporter scaffolds with BDP 581/591 to generate imaging reagents compatible with standard fluorescence instrumentation. By attaching the dye through thiol-reactive conjugation, users can tailor probe format and labeling density for microscopy readouts, plate-based fluorescence assays, and assay development screening.
3. Surface And Biomaterial Functionalization
BDP 581/591 maleimide is applied in biomaterials science to create fluorescently tagged surfaces and matrices by coupling the dye to thiol-functionalized materials. Materials researchers use thiol-bearing linkers on hydrogels, coatings, and nanoparticle surfaces to immobilize BODIPY fluorescence for tracking material distribution, studying surface interactions, and visualizing functionalized constructs under fluorescence microscopy. This labeling approach is also used to generate fluorescent standards and labeling controls for experiments where surface-associated signal is required.
4. Microscopy And Imaging Studies
BDP 581/591 maleimide-derived conjugates are widely used in fluorescence microscopy to visualize labeled biomolecules and biomaterial-associated components in fixed-sample workflows and imaging experiments. Microscopy users rely on the dye's BODIPY emission for clear signal in multi-color imaging panels when spectral separation is planned appropriately. The thiol-reactive conjugation strategy helps generate reproducible labeling of cysteine-containing targets, supporting localization studies, colocalization experiments, and quantitative imaging analyses.
Computed Properties
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 9 |
| Exact Mass | 514.1987772 g/mol |
| Monoisotopic Mass | 514.1987772 g/mol |
| Topological Polar Surface Area | 74.4Ų |
| Heavy Atom Count | 38 |
| Formal Charge | 0 |
| Complexity | 1150 |
| 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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