All Photos(1)
Synonym(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
Empirical Formula (Hill Notation):
C34H26N6O2 · 2CF3SO3
Recommended Products
Assay
≥97% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
2-8°C
SMILES string
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
Biochem/physiol Actions
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.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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André Miranda et al.
Pharmaceuticals (Basel, Switzerland), 14(2) (2021-02-10)
We have designed AS1411-N6, a derivative of the nucleolin (NCL)-binding aptamer AS1411, by adding six nucleotides to the 5'-end that are complementary to nucleotides at the 3'-end forcing it into a stem-loop structure. We evaluated by several biophysical techniques if
Anne De Cian et al.
Proceedings of the National Academy of Sciences of the United States of America, 104(44), 17347-17352 (2007-10-24)
Quadruplex ligands are often considered as telomerase inhibitors. Given the fact that some of these molecules are present in the clinical setting, it is important to establish the validity of this assertion. To analyze the effects of these compounds, we
Efficient suppression of gene expression by targeting 5'-UTR-based RNA quadruplexes with bisquinolinium compounds.
Kangkan Halder et al.
Chembiochem : a European journal of chemical biology, 12(11), 1663-1668 (2011-06-18)
Kevin Kok-Phen Yan et al.
Nucleic acids research, 49(14), 8339-8354 (2021-07-25)
The identification of G-quadruplex (G4) binding proteins and insights into their mechanism of action are important for understanding the regulatory functions of G4 structures. Here, we performed an unbiased affinity-purification assay coupled with mass spectrometry and identified 30 putative G4
Judith Lopes et al.
The EMBO journal, 30(19), 4033-4046 (2011-08-30)
G-quadruplexes are four-stranded nucleic acid structures whose biological functions remain poorly understood. In the yeast S. cerevisiae, we report that G-quadruplexes form and, if not properly processed, pose a specific challenge to replication. We show that the G-quadruplex-prone CEB1 tandem
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