SML2298

PhenDC3

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

• 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
• CAS Number: 929895-45-4
• Molecular Weight: 848.75
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥97% (HPLC)
• Form: powder

Properties

• Product Name: PhenDC3, ≥97% (HPLC)
• 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
• InChI: 1S/C34H24N6O2.2CHF3O3S/c1-39-19-25(17-23-7-3-5-9-29(23)39)35-33(41)27-15-13-21-11-12-22-14-16-28(38-32(22)31(21)37-27)34(42)36-26-18-24-8-4-6-10-30(24)40(2)20-26;2*2-1(3,4)8(5,6)7/h3-20H,1-2H3;2*(H,5,6,7)
• InChI key: PYJCATLYPXPYHF-UHFFFAOYSA-N

Description

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

High-affinity DNA and RNA G-quadruplex (G4) stabilizing ligand. A benchmark tool for probing cellular DNA and RNA G4 functions.

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable