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
MDL number:
UNSPSC Code:
12352106
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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
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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_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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.
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