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Czerwinska I.,Research Center for Bio microsensing Technology | Sato S.,Research Center for Bio microsensing Technology | Sato S.,Kyushu Institute of Technology | Takenaka S.,Research Center for Bio microsensing Technology | Takenaka S.,Kyushu Institute of Technology
Bioorganic and Medicinal Chemistry | Year: 2012

N,N′-bis[3-[3-(2,2′-dipicolyl)methylaminopropyl] -methylaminopropyl]naphthalene-1,4,5,8-tetracarboxylic acid diimide, 1, and its complex with zinc ions, 2, were investigated against telomeric sequences, [TAGGG(TTAGGG)3] and [AGGG(TTAGGG)3], which reveal different G-quadruplex structures depending on the conditions. Spectrophotometric, SPR, and CD techniques revealed that both ligands showed large binding constants to hybrid-type G-quadruplexes formed in the presence of K+ ions. Moreover, 2 revealed higher affinity to investigated oligonucleotides suggesting that complex of naphthalene diimide derivative with Zn2+, comparing to 1, provided additional electrostatic or coordination interactions between positively charged zinc ions and condensed negative charged phosphate anions from G4 DNA. © 2012 Elsevier Ltd. All rights reserved. Source


Czerwinska I.,Research Center for Bio microsensing Technology | Sato S.,Research Center for Bio microsensing Technology | Sato S.,Kyushu Institute of Technology | Juskowiak B.,Adam Mickiewicz University | And 2 more authors.
Bioorganic and Medicinal Chemistry | Year: 2014

Recently, strategy based on stabilization of G-quadruplex telomeric DNA by small organic molecule has been realized by naphthalene diimide derivatives (NDIs). At the same time NDIs bind to DNA duplex as threading intercalators. Here we present cyclic derivative of naphthalene diimide (ligand 1) as DNA-binding ligand with ability to recognition of different structures of telomeric G-quadruplexes and ability to bis-intercalate to double-stranded helixes. The results have been compared to non-cyclic derivative (ligand 2) and revealed that preferential binding of ligands to nucleic acids strongly depends on their topology and structural features of ligands. © 2014 Elsevier Ltd. All rights reserved. Source

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