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SML3867

Sigma-Aldrich

BI, Broccoli Fluorophore

≥98% (HPLC)

Synonym(s):

(5Z)-3-(1H-Benzimidazol-7-ylmethyl)-5-[(3,5-difluoro-4-hydroxyphenyl)methylene]-3,5-dihydro-2-methyl-4H-imidazol-4-one, (Z)-3-((1H-Benzo[d]imadazol-4-yl)methyl)-5-(3,5-difluoro-4-hydroxybenzylidene)-2-methyl-3,5-dihydro-4H-imidazol-4-one, BI, DFHBI-BI

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About This Item

Empirical Formula (Hill Notation):
C19H14F2N4O2
CAS Number:
Molecular Weight:
368.34
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

room temp

Biochem/physiol Actions

Cell-permeable DFHBI derivative that selectively binds to Broccoli aptamer; used for imaging of RNA in living cells.



BI is a cell-permeable DFHBI benzimidazolo (DFHBI-BI) derivative that greatly and selectively promotes and stabilizes Broccoli aptamer folding in vitro and cells with enhanced photostability. BI displays little background in vitro and cells (ϕ=0.00048, ϵ=42,500 M−1 cm−1), but very high fluorescence activation after binding to Broccoli (ϕ=0.669, ϵ=33,600 M−1 cm−1, KD = 51 nM). DFHBI-BI shows negligible cellular toxicity and binds Squash with much weaker affinity than Broccoli. Ex/Em: 470/505 nm.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Single mRNA Imaging with Fluorogenic RNA Aptamers and Small-molecule Fluorophores
Wei Chen, Xiaoying Zhao, Nanyang Yang, Xing Li
Angewandte Chemie (International Edition in English), 62(7) (2023)
Fluorophore-Promoted RNA Folding and Photostability Enables Imaging of Single Broccoli-Tagged mRNAs in Live Mammalian Cells
Angewandte Chemie (International ed. in English), 59(11), 4511-4518 (2020)
Sourav Kumar Dey et al.
Nature chemical biology, 18(2), 180-190 (2021-12-24)
Fluorogenic RNA aptamers are used to genetically encode fluorescent RNA and to construct RNA-based metabolite sensors. Unlike naturally occurring aptamers that efficiently fold and undergo metabolite-induced conformational changes, fluorogenic aptamers can exhibit poor folding, which limits their cellular fluorescence. To

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