title: The size of the aryl linker between two polyaza-cyclophane moieties controls the binding selectivity to ds-RNA vs. ds-DNA.
abstract: Aryl-linked (pyridine- vs. phenanthroline-) bis-polyaza pyridinophane scorpiands PYPOD and PHENPOD strongly bind to the double stranded DNA and RNA, whereby very intriguing RNA over DNA selectivity is finely tuned by aryl-linker length and aromatic surface. Moreover, PYPOD and PHENPOD dimer formation at high compound/polynucleotide ratios is highly sensitive to the fine interplay between the steric and binding properties of compound-dimers and the DNA minor groove/RNA major groove. That is demonstrated by significantly different induced CD spectra, which allow spectroscopic differentiation between various DNA/RNA secondary structures. A significantly higher (micromolar) antiproliferative effect of PYPOD and PHENPOD on human cell lines with respect to previously reported pyridine-based tripodal aliphatic polyamines is attributed to masked positive charges and increased hydrophobicity of novel compounds, resulting in more efficient membrane permeation and cellular uptake.
authors: ICMOL, Departamento de Química Inorgánica, Facultad de Química, Universidad de Valencia, C/Catedrático José Beltrán 2, 46980 Paterna, Valencia, Spain.
authors: Jorge
authors: J
authors: González-García
authors: Lidija
authors: L
authors: Uzelac
authors: Marijeta
authors: M
authors: Kralj
authors: José M
authors: JM
authors: Llinares
authors: Enrique
authors: E
authors: García-España
authors: Ivo
authors: I
authors: Piantanida
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D001665:Binding Sites; D004247:DNA / Q000737:chemistry*; D015394:Molecular Structure; D010316:Particle Size; D010618:Phenanthrolines / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D012330:RNA, Double-Stranded / Q000737:chemistry*
chemical_list: D001372:Aza Compounds; D010618:Phenanthrolines; D011725:Pyridines; D012330:RNA, Double-Stranded; D004247:DNA