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NAIA

Cat. No. 8910 提交评论 说明书 / 分析证书（CoA） / 化学品安全技术说明书（SDS）
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说明： Broad spectrum cysteine reactive probe; suitable for live-cell applications
别名： N-Acryloylindole-alkyne,NAIA-5
化学名： N-5-Hexyn-1-yl-2-[[1-(1-oxo-2-propen-1-yl)-1H-indol-5-yl]oxy]acetamide
纯度： ≥95% (HPLC)
说明书
引用文献
评论
生物活性 Scientific Data 技术数据 溶解性 计算器 说明书 参考文献

生物活性 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.

许可信息

Sold under license from Versitech Limited

技术数据 for NAIA

分子量 324.38
公式 C19H20N2O3
储存 Store at -20°C
纯度 ≥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

上方提供的技术数据仅供参考。批次相关数据请参见分析证书。

Tocris products are intended for laboratory research use only, unless stated otherwise.

溶解性数据 for NAIA

溶剂 最高浓度 mg/mL 最高浓度 mM
溶解性
DMSO 32.44 100

制备储备液 for NAIA

以下数据基于产品分子量 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.

选择批次从而根据批次分子量重新计算:
浓度/溶剂体积/质量 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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参考文献 for NAIA

参考文献是支持产品生物活性的出版物。

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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