
BDP 581/591 tetrazine
| Catalog Number | R08-0001 |
| Category | BODIPY |
| Molecular Formula | C32H28N7BF2O |
| Molecular Weight | 575.42 |
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Product Introduction
BDP 581/591 is a borondipyrromethene dye with red emission. The dye exhibits high emission quantum yield and molar extinction coefficient, relatively long fluorescence lifetime and two-photon cross section. Additionally, it can be used as an intracellular ROS sensor. This tetrazine derivative allows to conjugate the fluorophore with various strained dienophiles like trans-cyclooctenes in a fast reaction called TCO-ligation.
Chemical Information
Product Specification
Application
Computed Properties
Chemical Information
| 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]-N-[[4-(6-methyl-1,2,4,5-tetrazin-3-yl)phenyl]methyl]propanamide |
| SMILES | [B-]1(N2C(=CC=C2CCC(=O)NCC3=CC=C(C=C3)C4=NN=C(N=N4)C)C=C5[N+]1=C(C=C5)C=CC=CC6=CC=CC=C6)(F)F |
| InChI | InChI=1S/C32H28BF2N7O/c1-23-37-39-32(40-38-23)26-13-11-25(12-14-26)22-36-31(43)20-19-28-16-18-30-21-29-17-15-27(41(29)33(34,35)42(28)30)10-6-5-9-24-7-3-2-4-8-24/h2-18,21H,19-20,22H2,1H3,(H,36,43)/b9-5+,10-6+ |
| InChIKey | FJTGIDJJMYYWBZ-NXZHAISVSA-N |
| Solubility | well soluble in DMF, DMSO, dichloromethane, toluene |
| Appearance | colorless 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 tetrazine is a tetrazine-functional fluorescent labeling reagent designed for fast, bioorthogonal click chemistry with trans-cyclooctene (TCO)-bearing partners. Its BODIPY-derived emission in the 580-600 nm region supports fluorescence imaging workflows where rapid conjugation and bright signal are advantageous, including probe construction and biomolecule tagging for microscopy and flow cytometry development.
1. TCO-Biomolecule Labeling
BDP 581/591 tetrazine is used to label TCO-modified biomolecules such as proteins, peptides, and affinity reagents in fluorescence-based studies. Researchers incorporate the tetrazine dye during conjugate preparation to generate fluorescent bioconjugates for tracking binding interactions, monitoring conjugate stability in assay buffers, and visualizing labeled targets in cellular and biochemical experiments. This reagent is particularly valued in workflows that require rapid labeling after TCO functionalization, enabling efficient generation of fluorescent conjugates for downstream imaging or analytical readouts.
2. Fluorescence Microscopy Tracing
BDP 581/591 tetrazine is commonly applied to produce fluorescent imaging reagents by coupling tetrazine to TCO-tagged probes used for cellular and biomaterial visualization. In microscopy workflows, labeled constructs prepared with this reagent support localization studies of biomolecule distributions, labeling of probe-delivered components, and multi-step staining strategies where a tetrazine handle is introduced for later fluorescent "click-on" conjugation. The dye's orange-red emission region aligns well with standard fluorescence microscope filter sets used for 580-600 nm channels, facilitating integration into existing imaging panels.
3. Flow Cytometry Conjugate Preparation
BDP 581/591 tetrazine supports fluorescence labeling of TCO-bearing targets for flow cytometry sample preparation, including antibody-like reagents, protein conjugates, and other fluorescent tagging constructs used in single-cell analysis. By performing tetrazine-TCO click conjugation under typical labeling conditions, researchers generate fluorescent conjugates that can be used to quantify labeled populations, compare binding outcomes across experimental conditions, and evaluate labeling consistency in multiplex staining panels. This application is especially relevant when rapid, covalent attachment helps reduce variability from noncovalent dye association.
4. Fluorescent Probe Construction
BDP 581/591 tetrazine is used in fluorescent probe development where a tetrazine dye is introduced as a modular component for later assembly with TCO-functional recognition elements. Probe developers use this reagent to create imaging reagents with defined stoichiometry by attaching the BDP fluorophore to TCO-bearing scaffolds such as affinity ligands, targeting peptides, or engineered probe platforms. The resulting fluorescent conjugates are then deployed in molecular imaging experiments, assay development, and platform validation studies that require reproducible fluorescence labeling chemistry rather than passive dye adsorption.
Computed Properties
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 9 |
| Exact Mass | 575.2416450 g/mol |
| Monoisotopic Mass | 575.2416450 g/mol |
| Topological Polar Surface Area | 88.6Ų |
| Heavy Atom Count | 43 |
| 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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