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908401

Sigma-Aldrich

1-Methyl-7-nitroisatoic anhydride

Synonym(s):

1-Methyl-7-nitro-2H-3,1-benzoxazine-2,4(1H)-dione, 1-methyl-7-nitro-2H-3,1-Benzoxazine-2,4(1H)-dione, 1M7, RNA SHAPE probe, Reagent for RNA SHAPE-MaP

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About This Item

Empirical Formula (Hill Notation):
C9H6N2O5
CAS Number:
73043-80-8
Molecular Weight:
222.15
MDL number:
MFCD18432729
UNSPSC Code:
12352119
NACRES:
NA.22

form

powder

mp

204.5 °C

storage temp.

2-8°C

InChI

1S/C9H6N2O5/c1-10-7-4-5(11(14)15)2-3-6(7)8(12)16-9(10)13/h2-4H,1H3

InChI key

MULNCJWAVSDEKJ-UHFFFAOYSA-N

Application

1-Methyl-7-nitroisatoic anhydride (1M7) is used as an in vivo SHAPE-MaP reagent for live cell RNA structure analysis at single nucleotide resolution. SHAPE -- or selective 2′-hydroxyl acylation analyzed by primer extension -- uses small, electrophilic chemical probes such as 1M7 to react with the 2′-hydroxyl group and provides insight to RNA structure. When combined with mutational profiling (MaP), quantitative nucleotide measurements are possible for entire transciptomes. Together, these methods deepen the understanding of RNA interactions and regions that may be exploited for design of RNA-targeting small-molecule drugs.

Other Notes

Pervasive Regulatory Functions of mRNA Structure Revealed by High-Resolution SHAPE Probing

SnapShot: RNA Structure Probing Technologies

Detection of RNA-Protein Interactions in Living Cells with SHAPE

Standardization of RNA Chemical Mapping Experiments

In-cell RNA structure probing with SHAPE-MaP

A Fast-Acting Reagent for Accurate Analysis of RNA Secondary and Tertiary Structure by SHAPE Chemistry

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Katherine E Deigan et al.
Proceedings of the National Academy of Sciences of the United States of America, 106(1), 97-102 (2008-12-26)
Almost all RNAs can fold to form extensive base-paired secondary structures. Many of these structures then modulate numerous fundamental elements of gene expression. Deducing these structure-function relationships requires that it be possible to predict RNA secondary structures accurately. However, RNA
Kady-Ann Steen et al.
Nature protocols, 6(11), 1683-1694 (2011-10-08)
RNA SHAPE chemistry yields quantitative, single-nucleotide resolution structural information based on the reaction of the 2'-hydroxyl group of conformationally flexible nucleotides with electrophilic SHAPE reagents. However, SHAPE technology has been limited by the requirement that sites of RNA modification be
Paul D Carlson et al.
Cell, 175(2), 600-600 (2018-10-06)
Chemical probing coupled to high-throughput sequencing offers a flexible approach to uncover many aspects of RNA structure relevant to its cellular function. With a wide variety of chemical probes available that each report on different features of RNA molecules, a
Kelly Phelps et al.
ACS chemical biology, 7(1), 100-109 (2011-12-14)
The past several years have seen numerous reports of new chemical modifications for use in RNA. In addition, in that time period, we have seen the discovery of several previously unknown naturally occurring modifications that impart novel properties on the
Kevin A Wilkinson et al.
RNA (New York, N.Y.), 15(7), 1314-1321 (2009-05-22)
Hydroxyl-selective electrophiles, including N-methylisatoic anhydride (NMIA) and 1-methyl-7-nitroisatoic anhydride (1M7), are broadly useful for RNA structure analysis because they react preferentially with the ribose 2'-OH group at conformationally unconstrained or flexible nucleotides. Each nucleotide in an RNA has the potential
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