
BDP 581/591 NHS ester | CAS 654651-21-5
| Catalog Number | R01-0006 |
| Category | BODIPY |
| Molecular Formula | C26H22N3BF2O4 |
| Molecular Weight | 489.28 |
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Product Introduction
BDP 581/591 is a borondipyrromethene dye that has relatively long fluorescence lifetime and two photon excitation cross section. It is useful for fluorescence polarization assays. Due to the presence of a diene system, it can react with reactive oxygen species (ROS) with a change of fluorescence. This is the NHS ester derivative for the conjugation with primary and secondary amine groups of proteins, peptides, and other molecules.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| Synonyms | BDP581/591NHSester |
| Purity | NMR 1H, HPLC-MS (95%) |
| IUPAC Name | (2,5-dioxopyrrolidin-1-yl) 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]propanoate |
| SMILES | [B-]1(N2C(=CC=C2CCC(=O)ON3C(=O)CCC3=O)C=C4[N+]1=C(C=C4)C=CC=CC5=CC=CC=C5)(F)F |
| InChI | InChI=1S/C26H22BF2N3O4/c28-27(29)30-20(9-5-4-8-19-6-2-1-3-7-19)10-12-22(30)18-23-13-11-21(31(23)27)14-17-26(35)36-32-24(33)15-16-25(32)34/h1-13,18H,14-17H2/b8-4+,9-5+ |
| InChIKey | HHJAMTPLXKVOAY-KBXRYBNXSA-N |
| Solubility | good in DMF, DMSO, DCM |
| Appearance | dark colored solid |
Product Specification
| ε, L⋅mol-1⋅cm-1 | 104000 |
| Fluorescence Quantum Yield | 0.83 |
| Excitation | 585 |
| Emission | 594 |
| 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 581/591 NHS ester is a reactive, NHS-ester-functionalized BODIPY dye designed for covalent fluorescent labeling of primary amines. Its bright orange-red fluorescence (581/591 nm emission region) makes it a common choice for building fluorescent conjugates for microscopy and quantitative fluorescence workflows, where stable dye attachment to proteins or peptides is required. Because the dye is pre-activated as an N-hydroxysuccinimide ester, it is routinely used to generate amine-reactive labeling reagents for bioconjugation and downstream imaging assays.
1. Protein And Antibody Labeling
BDP 581/591 NHS ester is widely used to fluorescently label proteins, including antibodies, antibody fragments, and affinity reagents, by targeting accessible lysine residues and N-terminal amines. Researchers incorporate the resulting BDP-labeled biomolecules into immunofluorescence staining, binding studies, and imaging experiments where orange-red emission provides separation from common green-channel fluorophores. In practice, the NHS-ester format supports straightforward conjugate preparation for microscopy platforms and fluorescence-based binding readouts, enabling consistent dye loading for reagent development and assay optimization.
2. Peptide and Biomolecule Conjugation
BDP 581/591 NHS ester supports covalent labeling of peptides and other amine-containing biomolecules used as targeting ligands, affinity tags, or assay components. Chemical biology teams often prepare BDP-labeled peptides for receptor-binding studies, cellular uptake experiments, and fluorescence tracking of biomolecular interactions, leveraging the dye's strong emission in the 581/591 region to improve channel compatibility. The NHS-ester reactivity makes it useful when a stable, non-bleaching covalent dye attachment is preferred over passive adsorption or weaker dye conjugation approaches.
3. Fluorescent Labeling For Flow Cytometry
BDP 581/591 NHS ester is used to generate flow cytometry dyes and labeled detection reagents by covalently attaching the fluorophore to amine-bearing proteins used in immunostaining panels. Flow cytometry users value the orange-red spectral window for multiplexing experiments where separation from green and far-red channels is needed, and where consistent labeling chemistry helps reduce variability between conjugate lots. The covalent NHS-ester labeling strategy also supports preparation of stained standards and labeled controls for instrument setup, gating development, and comparative fluorescence measurements across samples.
4. Fluorescent Probe And Assay Reagent Development
BDP 581/591 NHS ester serves as a building block for fluorescent probe construction and fluorescence assay reagent development, particularly when a stable amine-reactive dye is required to tag assay components. In research settings, teams conjugate the dye to proteins, peptides, or other amine-functional reagents to create fluorescent readouts for binding assays, wash-based immunoassays, and microscopy-compatible labeling reagents. The BDP scaffold's strong fluorescence in the 581/591 region supports assay design where robust signal generation from covalently labeled components is important for reproducible experimental workflows.
Computed Properties
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 8 |
| Exact Mass | 489.1671427 g/mol |
| Monoisotopic Mass | 489.1671427 g/mol |
| Topological Polar Surface Area | 71.6Ų |
| Heavy Atom Count | 36 |
| Formal Charge | 0 |
| Complexity | 1070 |
| 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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