Cyclic Naphthalene Diimide with a Ferrocene Moiety as a Redox-Active Tetraplex-DNA Ligand.

Autor: Kaneyoshi S; Department of Applied Chemistry, Kyushu Institute of Technology, Fukuoka, 804-8550, Japan., Zou T; Department of Applied Chemistry, Kyushu Institute of Technology, Fukuoka, 804-8550, Japan.; Research Center for Bio-microsensing Technology, Kyushu Institute of Technology, Fukuoka, 804-8550, Japan., Ozaki S; Department of Applied Chemistry, Kyushu Institute of Technology, Fukuoka, 804-8550, Japan., Takeuchi R; Department of Applied Chemistry, Kyushu Institute of Technology, Fukuoka, 804-8550, Japan., Udou A; Department of Applied Chemistry, Kyushu Institute of Technology, Fukuoka, 804-8550, Japan., Nakahara T; Department of Applied Chemistry, Kyushu Institute of Technology, Fukuoka, 804-8550, Japan., Fujimoto K; Department of Applied Chemistry and Biochemistry, Kyushu Sangyo University, Fukuoka, 813-8503, Japan., Fujii S; Department of Bioscience and Bioinformatics, Kyushu Institute of Technology, Fukuoka, 820-8502, Japan., Sato S; Department of Applied Chemistry, Kyushu Institute of Technology, Fukuoka, 804-8550, Japan.; Research Center for Bio-microsensing Technology, Kyushu Institute of Technology, Fukuoka, 804-8550, Japan., Takenaka S; Department of Applied Chemistry, Kyushu Institute of Technology, Fukuoka, 804-8550, Japan.; Research Center for Bio-microsensing Technology, Kyushu Institute of Technology, Fukuoka, 804-8550, Japan.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2020 Jan 02; Vol. 26 (1), pp. 139-142. Date of Electronic Publication: 2019 Dec 05.
DOI: 10.1002/chem.201903883
Abstrakt: Cyclic naphthalene diimides (cNDIs), with a ferrocene moiety (cFNDs) and different linker lengths between the ferrocene and cNDI moieties, were designed and synthesized as redox-active, tetraplex-DNA ligands. Intramolecular stacking was observed between ferrocene and the NDI planes, which could affect the binding properties for G-quadruplexes. Interestingly, the circular dichroism spectrum of one of these compounds clearly shows new Cotton effects around 320-380 and 240 nm, which can be considered a direct evidence of intramolecular stacking of ferrocene and the NDI. Regarding recognition of hybrid G-quadruplexes, the less rigid structures (longer linkers) show higher binding affinity (10 6  m -1 order of magnitude). All new compounds show higher selectivity for G4 during electrochemical detection than noncyclic FND derivatives, which further identifies the redox-active potentiality of the cFNDs. Two of the three compounds tested even show preferential inhibition of cell growth in cancer cells over normal cells in a low concentration range, highlighting the potential for bioapplications of these cFNDs.
(© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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