913812

2-(Azidomethyl)nicotinic acid imidazolide

≥95%

• Synonym(s): 2-(Azidomethyl)-3-(1H-imidazole-1-carbonyl)pyridine, NAI-N3, RNA SHAPE probe, icSHAPE reagent
• Empirical Formula (Hill Notation): C₁₀H₈N₆O
• CAS Number: 1612756-29-2
• Molecular Weight: 228.21
• MDL number: MFCD31560475
• UNSPSC Code: 12352106

Properties

• Quality Level: 100
• Assay: ≥95%
• form: powder
• mp: 74-80 °C
• storage temp.: −20°C
• SMILES string: [N+](=[N-])=NCc1ncccc1C(=O)[n]2cncc2
• InChI: 1S/C10H8N6O/c11-15-14-6-9-8(2-1-3-13-9)10(17)16-5-4-12-7-16/h1-5,7H,6H2
• InChI key: QPSQVTFTPHUCEH-UHFFFAOYSA-N

Description

Application

2-(Azidomethyl)nicotinic acid imidazolide (NAI-N3) is an RNA icSHAPE probe for live-cell RNA structure profiling across the genome. icSHAPE -- or in vivo click selective 2′-hydroxyl acylation and profiling experiment -- uses NAI-N3 in a chemoaffinity method to probe RNA structure. NAI-N3 is an azido version of the cell-permeable SHAPE reagent 2-methylnicotinic acid imidazolide (NAI) that permits the tagging of NAI-N3-modified RNA with a biotin moiety for subsequent capture via streptavidin. Not only do such strategies further the understanding of RNA structure in living cells but also provide a tool for identifying regions that may be susceptible to therapeutic targeting. Recently, the azidomethylnicotinyl (AMN) group of NAI-N3 was demonstrated to block the function of gRNA and CRISPR systems, which could be reactivated by removing the AMN groups with Staudinger reduction (DPBM phosphine), overall providing a means to control nucleic acid cleavage and gene editing in live cells.

Other Notes

Conditional control of RNA-guided nucleic acid cleavage and gene editing

SnapShot: RNA Structure Probing Technologies

Multiplex Aptamer Discovery through Apta-Seq and Its Application to ATP Aptamers Derived from Human-Genomic SELEX

Structural imprints in vivo decode RNA regulatory mechanisms

Safety Information

• Pictograms: GHS02,GHS07
• Signal Word: Danger
• Hazard Statements: H242,H315,H319
• Precautionary Statements: P210 - P235 - P302 + P352 - P305 + P351 + P338 - P370 + P378 - P403
• Hazard Classifications: Eye Irrit. 2 - Self-react. C - Skin Irrit. 2
• Storage Class Code: 5.2 - Organic peroxides and self-reacting hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable