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• W3092463494 endingPage "111270" @default.
• W3092463494 startingPage "111270" @default.
• W3092463494 abstract "Interaction between an Ga(III) phthalocyanine (Pc) derivative bearing eight N -methylpyridinium groups at peripheral β-positions (2,3,6,7,10,11,14,15-octakis-[ N -methyl-(4-methylpyridinium-3-yloxy)phthalocyaninato] chloro gallium(III) iodide (GaPc)) and an all parallel-stranded tetrameric G-quadruplex formed from a heptanucleotide d(TTAGGGT) ([d(TTAGGGT)] 4 ) has been investigated to elucidate the molecular recognition of G-quadruplex DNA by the Pc derivative, which provides a useful insight as to the design of G-quadruplex ligands suitable for various in vitro and in vivo applications. We found that GaPc binds to the A3G4 and G6T7 steps of [d(TTAGGGT)] 4 , with binding constants of (21 ± 2) × 10 6 and (0.09 ± 0.06) × 10 6 M −1 , respectively, to form a 2:1 complex. Obviously, upon the binding of GaPc to each of the sites, the π-π stacking and electrostatic interactions of the Pc moiety and positively-charged side chains of GaPc with a G-quartet and the negatively-charged phosphate groups in nearby phosphodiester bonds of the DNA, respectively, are major driving forces for the complexation. Considering the similarity in the local structural environment between the A3G4 and G6T7 steps of [d(TTAGGGT)] 4 , the remarkably large difference in the GaPc-binding affinity between them is most likely accounted for by the effect of the polarity of the GaPc-binding site on the intermolecular electrostatic interaction. This finding provides valuable insights as to the design of Pc derivatives as G-quadruplex ligands. A cationic gallium(III) phthalocyanine derivative binds to the A3G4 and G6T7 steps of a parallel G-quadruplex DNA formed from d(TTAGGGT), with binding constants ( K a s) of ~21 μM −1 and ~0.09 μM −1 , respectively, to form a 2:1 complex. The polarity of the binding site is possibly responsible for determining the K a . • A cationic Ga(III) phthalocyanine derivative (GaPc) binds to a parallel G-quadruplex DNA. • GaPc exhibits stepwise binding to the G-quadruplex DNA to form a 2:1 GaPc-DNA complex. • The polarity of the binding site alters the GaPc-binding affinity to the DNA." @default.
• W3092463494 created "2020-10-15" @default.
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• W3092463494 date "2020-12-01" @default.
• W3092463494 modified "2023-10-17" @default.
• W3092463494 title "Stepwise binding of a cationic phthalocyanine derivative to an all parallel-stranded tetrameric G-quadruplex DNA" @default.
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• W3092463494 doi "https://doi.org/10.1016/j.jinorgbio.2020.111270" @default.
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