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SML2298

Sigma-Aldrich

PhenDC3

≥97% (HPLC), powder, G-quadruplex ligand

Synonyme(s) :

3,3′-[1,10-Phenanthroline-2,9-diylbis(carbonylimino)]bis[1-methylquinolinium] 1,1,1-trifluoromethanesulfonate (1:2), Phen DC3, Phen-DC(3), Phen-DC3

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About This Item

Formule empirique (notation de Hill):
C34H26N6O2 · 2CF3SO3
Numéro CAS:
929895-45-4
Poids moléculaire :
848.75
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

product name

PhenDC3, ≥97% (HPLC)

Pureté

≥97% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

O=C(NC1=CC2=CC=CC=C2[N+](C)=C1)C3=CC=C4C=CC5=CC=C(N=C5C4=N3)C(NC6=CC7=CC=CC=C7[N+](C)=C6)=O.O=S([O-])(C(F)(F)F)=O.O=S([O-])(C(F)(F)F)=O

Application

PhenDC3 has been used:
  • as a quadruplex (G4) ligand to study its effects on the binding of RNA quadruplex (rG4) to nucleolin (NCL)
  • as a DNA/RNA G-quadruplexes (GQs) ligand to study its effects on the expression of double homeobox 4 (DUX4) gene
  • as a G4 ligand to study its stability and selectivity towards pre-miR-92b rG4 complex and duplex DNA by fluorescence resonance energy transfer (FRET)-melting assay

Actions biochimiques/physiologiques

PhenDC3 (Phen-DC3) is a bisquinolinium-derivatized phenanthroline-dicarboxamide that targets both DNA and RNA G-quadruplex (G4) structure with high affinity (DNA DC50 in μM = 0.31/22AG K+, 0.25/22AG Na+, 0.30/TBA; RNA DC50 in μM = 0.11/(G3U)3G3, 0.12/(G3U2)3G3, 0.16/(G3U3)3G3) and selectivity (duplex DNA DC50 >2.5 μM). PhenDC3 suppresses the translation of reporter mRNA constructs with 5′UTR G4 structure, but not those without, in cell-based reporter assays (0.1-10 μM) and reduces telomerase processivity by promoting telomerase dissociation from its product during elongation. NMR analysis shows that PhenDC3 interacts with the quadruplex through extensive stacking with the guanine bases of the top G-quartet. A powerful benchmark tool for probing and elucidating the biological roles of cellular DNA and RNA G4 sturctures.

Code de la classe de stockage

11 - Combustible Solids

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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Aurèle Piazza et al.
Nucleic acids research, 38(13), 4337-4348 (2010-03-13)
G-quadruplexes are nucleic acid secondary structures for which many biological roles have been proposed but whose existence in vivo has remained elusive. To assess their formation, highly specific G-quadruplex ligands are needed. Here, we tested Phen-DC(3) and Phen-DC(6), two recently
Aleksandr B Sahakyan et al.
Nature structural & molecular biology, 24(3), 243-247 (2017-01-31)
Long interspersed nuclear elements (LINEs) are ubiquitous transposable elements in higher eukaryotes that have a significant role in shaping genomes, owing to their abundance. Here we report that guanine-rich sequences in the 3' untranslated regions (UTRs) of hominoid-specific LINE-1 elements
Highly efficient G-quadruplex recognition by bisquinolinium compounds.
Anne De Cian et al.
Journal of the American Chemical Society, 129(7), 1856-1857 (2007-01-31)
Tovah A Day et al.
Nature communications, 8, 15110-15110 (2017-04-28)
Chromosomal rearrangements are essential events in the pathogenesis of both malignant and nonmalignant disorders, yet the factors affecting their formation are incompletely understood. Here we develop a zinc-finger nuclease translocation reporter and screen for factors that modulate rearrangements in human
D Monchaud et al.
Biochimie, 90(8), 1207-1223 (2008-03-18)
We report here the details of G4-FID (G-quadruplex fluorescent intercalator displacement), a simple method aiming at evaluating quadruplex-DNA binding affinity and quadruplex- over duplex-DNA selectivity of putative ligands. This assay is based on the loss of fluorescence upon displacement of
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