
JOE azide, 5-isomer
| Catalog Number | F12-0001 |
| Category | JOE Dyes |
| Molecular Formula | C26H20N4Cl2O8 |
| Molecular Weight | 587.37 |
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Product Introduction
JOE is a fluorescent dye with the emission in yellow region of the spectrum. The fluorophore matches channel of HEX dye, another chlorinated fluorescein.JOE dye is often used in qPCR; oligo labeling can be achieved using Click chemistry. This is an azide derivative of JOE for Click chemistry, pure 5-isomer.
Chemical Information
Product Specification
Application
Computed Properties
Patents
Chemical Information
| Purity | NMR 1H, HPLC-MS (95%) |
| IUPAC Name | N-(3-azidopropyl)-4',5'-dichloro-3',6'-dihydroxy-2',7'-dimethoxy-3-oxospiro[2-benzofuran-1,9'-xanthene]-5-carboxamide |
| SMILES | COC1=C(C(=C2C(=C1)C3(C4=C(C=C(C=C4)C(=O)NCCCN=[N+]=[N-])C(=O)O3)C5=CC(=C(C(=C5O2)Cl)O)OC)Cl)O |
| InChI | InChI=1S/C26H20Cl2N4O8/c1-37-16-9-14-22(18(27)20(16)33)39-23-15(10-17(38-2)21(34)19(23)28)26(14)13-5-4-11(8-12(13)25(36)40-26)24(35)30-6-3-7-31-32-29/h4-5,8-10,33-34H,3,6-7H2,1-2H3,(H,30,35) |
| InChIKey | HEOCCOHXKKBACD-UHFFFAOYSA-N |
| Solubility | good in DMF, DMSO |
| Appearance | red solid |
Product Specification
| ε, L⋅mol-1⋅cm-1 | 75000 |
| Excitation | 533 |
| Emission | 554 |
| 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
JOE azide, 5-isomer is an azide-functional fluorescent labeling reagent designed for copper-catalyzed azide-alkyne cycloaddition (CuAAC) workflows. As a fluorophore-bearing azide, it enables post-labeling installation of JOE-derived fluorescence into biomolecules, polymers, and surfaces through click chemistry, supporting fluorescence imaging and assay development where robust conjugation is required.
1. Biomolecule Click Labeling
JOE azide, 5-isomer is used by chemical biology and fluorescence microscopy groups to introduce JOE fluorescence into proteins, peptides, and other biomolecules that have been equipped with complementary alkyne handles. In labeling workflows, researchers typically prepare alkyne-functional targets (for example, via amine-reactive or cysteine-reactive strategies in upstream steps) and then perform CuAAC to obtain stable triazole-linked fluorescent conjugates. This approach is commonly used when a modular labeling strategy is preferred, such as comparing multiple labeling densities, generating reference standards, or building conjugates for downstream imaging and quantitative fluorescence readouts.
2. Oligonucleotide Modification
JOE azide, 5-isomer supports fluorescence tagging of nucleic acids in molecular biology workflows that rely on azide-alkyne click conjugation. Researchers use it to attach fluorescent JOE signal to alkyne-modified oligonucleotides for hybridization-based experiments, probe construction, and nucleic-acid tracing studies where a defined fluorophore position is important. The azide functionality allows modular probe assembly, enabling rapid exchange of fluorescent labels across different oligo sequences or assay formats without redesigning the entire oligonucleotide synthesis.
3. Fluorescent Probe Construction
JOE azide, 5-isomer is frequently incorporated into custom fluorescent probe development where a fluorophore needs to be appended to a targeting scaffold via click chemistry. In practice, probe developers functionalize a recognition element or reporter scaffold with an alkyne group and then use JOE azide, 5-isomer to install the fluorescent reporter through CuAAC, producing triazole-linked fluorescent conjugates suitable for microscopy and fluorescence-based assays. This strategy is especially useful for building modular probe libraries, optimizing labeling positions, and generating consistent fluorescent readouts for method development in chemical biology and materials screening.
4. Surface and Polymer Functionalization
JOE azide, 5-isomer is used in biomaterials and materials research to fluorescently tag surfaces, hydrogels, and polymer films that present alkyne functionalities. Researchers can create fluorescently addressable materials by click-immobilizing JOE signal onto alkyne-bearing coatings, enabling visualization of material distribution, tracking of functional layer formation, and development of fluorescence readout platforms for assay integration. The azide-based click handle also supports iterative material engineering, where fluorescent labeling can be introduced after surface preparation while maintaining the integrity of other functional groups on the material.
Computed Properties
| XLogP3 | 5.2 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 10 |
| Rotatable Bond Count | 7 |
| Exact Mass | 586.0658190 g/mol |
| Monoisotopic Mass | 586.0658190 g/mol |
| Topological Polar Surface Area | 138Ų |
| Heavy Atom Count | 40 |
| Formal Charge | 0 |
| Complexity | 981 |
| 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 |
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| US-2014024137-A1 | Methods and compositions related to nucleic acid binding assays | 2012-07-11 |
| US-2014330001-A1 | Methods and compositions related to nucleic acid binding assays | 2012-07-11 |
| US-2016282357-A1 | Methods and compositions related to nucleic acid binding assays | 2012-07-11 |
| US-9017943-B2 | Methods and compositions related to nucleic acid binding assays | 2012-07-11 |
| US-9410186-B2 | Methods and compositions related to nucleic acid binding assays | 2012-07-11 |
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