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Description: Broad spectrum cysteine reactive probe; suitable for live-cell applications
Alternative Names: N-Acryloylindole-alkyne,NAIA-5
Chemical Name: N-5-Hexyn-1-yl-2-[[1-(1-oxo-2-propen-1-yl)-1H-indol-5-yl]oxy]acetamide
Purity: ≥95% (HPLC)
Biological Activity for NAIA
NAIA (N-Acryloylindole-alkyne) is a broad-spectrum cysteine reactive probe enabling cysteine profiling and imaging. It covalently binds cysteine residues in proteins.
Displays faster reaction kinetics with CYS (k > 102 M-1 s-1) and targets an expanded pool of ligandable cysteines and proteins compared to IA-Alkyne (Cat. No. 7015). Also shows higher stability and selectivity for CYS over SER and LYS than IA-Alkyne (Cat. No. 7015).
NAIA is used in chemoproteomics experiments as a click-chemistry handle to attach a fluorophore or biotin to reactive cysteines in proteins for visualization by in-gel fluorescence or identification by mass spectrometry, respectively. NAIA can also be used to image oxidized cysteines in cells under oxidative stress by confocal fluorescence microscopy.
Cell-permeable and non-cytotoxic, NAIA is suitable for live-cell experiments.
Licensing Information
Sold under license from Versitech Limited
Technical Data for NAIA
| M. Wt | 324.38 |
| Formula | C19H20N2O3 |
| Storage | Store at -20°C |
| Purity | ≥95% (HPLC) |
| CAS Number | 3020685-33-7 |
| InChI Key | STJKPWRTQBLLKC-UHFFFAOYSA-N |
| Smiles | O=C(C=C)N1C=CC=2C=C(OCC(=O)NCCCCC#C)C=CC21 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for NAIA
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 32.44 | 100 |
Preparing Stock Solutions for NAIA
The following data is based on the product molecular weight 324.38. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 3.08 mL | 15.41 mL | 30.83 mL |
| 5 mM | 0.62 mL | 3.08 mL | 6.17 mL |
| 10 mM | 0.31 mL | 1.54 mL | 3.08 mL |
| 50 mM | 0.06 mL | 0.31 mL | 0.62 mL |
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Product Datasheets for NAIA
References for NAIA
References are publications that support the biological activity of the product.
Koo et al (2023) N-Acryloylindole-alkyne (NAIA) enables imaging and profiling new ligandable cysteines and oxidized thiols by chemoproteomics. Nat. Commun 14 3564 PMID: 37322008
If you know of a relevant reference for NAIA, please let us know.
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