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913812

Sigma-Aldrich

2-(Azidomethyl)nicotinic acid imidazolide

≥95%

Synonyme(s) :

2-(Azidomethyl)-3-(1H-imidazole-1-carbonyl)pyridine, NAI-N3, RNA SHAPE probe, icSHAPE reagent

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About This Item

Formule empirique (notation de Hill):
C10H8N6O
Numéro CAS:
1612756-29-2
Poids moléculaire :
228.21
Numéro MDL:
MFCD31560475
Code UNSPSC :
12352106

Niveau de qualité

100

Essai

≥95%

Forme

powder

Pf

74-80 °C

Température de stockage

−20°C

Chaîne SMILES 

[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

Clé InChI

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.

Autres remarques

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

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

115959

Benzoyl cyanide, 98%

320293

Dimethyl sulfate, ≥99%

908401

1-Methyl-7-nitroisatoic anhydride

913839

2-Methylnicotinic acid imidazolide

914487

2-(Diphenylphosphanyl)benzamide, ≥95%

914983

ThT-NE, ≥95%

914274

DMOTY TEA, ≥95%

Pictogrammes

FlameExclamation mark
GHS02,GHS07

Mention d'avertissement

Danger

Mentions de danger

H242,H315,H319

Classification des risques

Eye Irrit. 2 - Self-react. C - Skin Irrit. 2

Code de la classe de stockage

5.2 - Organic peroxides and self-reacting hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

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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
Pengfei Wang et al.
PloS one, 13(11), e0207344-e0207344 (2018-11-10)
Foxtail millet is very a drought-tolerant crop. Basic helix-loop-helix (bHLH) transcription factors are involved in many drought-stress responses, but foxtail millet bHLH genes have been scarcely examined. We identified 149 foxtail millet bHLH genes in a genome-wide analysis and performed

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