913812
2-(Azidomethyl)nicotinic acid imidazolide
≥95%
Synonym(s):
2-(Azidomethyl)-3-(1H-imidazole-1-carbonyl)pyridine, NAI-N3, RNA SHAPE probe, icSHAPE reagent
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About This Item
Empirical Formula (Hill Notation):
C10H8N6O
CAS Number:
Molecular Weight:
228.21
UNSPSC Code:
12352106
MDL number:
NACRES:
NA.21
Assay:
≥95%
Form:
powder
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
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
signalword
Danger
hcodes
Hazard Classifications
Eye Irrit. 2 - Self-react. C - Skin Irrit. 2
Storage Class
5.2 - Organic peroxides and self-reacting hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Michael M Abdelsayed et al.
ACS chemical biology, 12(8), 2149-2156 (2017-07-01)
Laboratory-evolved RNAs bind a wide variety of targets and serve highly diverse functions, including as diagnostic and therapeutic aptamers. The majority of aptamers have been identified using in vitro selection (SELEX), a molecular evolution technique based on selecting target-binding RNAs
Robert C Spitale et al.
Nature, 519(7544), 486-490 (2015-03-25)
Visualizing the physical basis for molecular behaviour inside living cells is a great challenge for biology. RNAs are central to biological regulation, and the ability of RNA to adopt specific structures intimately controls every step of the gene expression program.
Fuyou Fu et al.
Scientific reports, 7(1), 2580-2580 (2017-06-02)
Macrosclereid cells, which are a layer in the seed coat of Medicago truncatula, accumulate large amounts of phytochemicals during their development. But little is known about the complex and dynamic changes during macrosclereid cell development. To characterize the phytochemicals and
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 913812-250MG | 04061842052639 |
| 913812-50MG | 04061842052646 |