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NAIA

Cat. No. 8910 Submit a Review Datasheet / COA / SDS
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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)
Datasheet
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Biological Activity Scientific Data Technical Data Solubility Calculators Datasheets References

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.

Scientific Data

Confocal Microscopy Application of NAIA in HepG2 cells. View Larger

Application of NAIA. HepG2 cells were incubated with NAIA (10 µM) in complete medium for 60 min. The cells were then washed with PBS, fixed by 4% paraformaldehyde, permeabilized, and reacted with azide-fluor 545 (20 µM) by CuAAC reaction at room temperature in the dark for 1 h. The stained cells were washed with PBS and further incubated with Hoechst (8.2 µM) for 15 min. The cells were then washed with PBS and imaged by confocal fluorescence microscopy.

Mass Spectrometry Application for NAIA for Mass spectrometry experiment View Larger

Application for NAIA. HepG2 cells were treated with solvent vehicle, H2O2 (1 mM) or H2O2 (1 mM) + NAC (5 mM) in a serum-free medium for 15 min at 37 °C. The cells were then incubated with NAI (50 µM; 10 min) to label-free thiols in live cells, followed by cell lysis and TCEP (1 mM) reduction for 1 h. After acetone precipitation at -20 °C overnight, the proteins were labeled by NAIA-5 (100 µM) in PBS. The samples were then prepared for MS and analyzed by LC-MS/MS.

Application for NAIA in Gel-based ABPP experiment View Larger

Application for NAIA in Gel-based ABPP experiment. HepG2 cell lysates (100 µg) in PBS were incubated with NAIA for 60 min, followed by copper-catalyzed azide-alkyne cycloaddition reaction with azide-fluor 545 (25 µM). The protein mixtures were then boiled with sampling buffer, resolved by SDS-PAGE and imaged.

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
PubChem ID 171403789
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.

Select a batch to recalculate based on the batch molecular weight:
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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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

Koo et al (2025) Activity-based protein profiling for functional cysteines and protein target identification Methods Mol.Biol. 2921 331 PMID: 40515999

If you know of a relevant reference for NAIA, please let us know.

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