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9,10-Bis[(4-(2-hydroxyethyl)piperazine-1-yl)prop-2-yne-1-yl]anthracene: Synthesis and G-quadruplex Selectivity

Department of Molecular and Translational Medicine, University of Brescia, 25121 Brescia, Italy
Department of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131 Padova, Italy
Author to whom correspondence should be addressed.
Molbank 2020, 2020(2), M1138;
Received: 24 April 2020 / Revised: 19 May 2020 / Accepted: 19 May 2020 / Published: 22 May 2020
(This article belongs to the Section Organic Synthesis)
G-quadruplex DNA is the target of several natural and synthetic small molecules with antiproliferative and antiviral activity. We here report the synthesis through Sonogashira reaction and A3 coupling of a disubstituted anthracene derivative, 9,10-bis[(4-(2-hydroxyethyl)piperazine-1-yl)prop-2-yne-1-yl]anthracene. The binding of this compound to G-quadruplex and double stranded DNA sequences was evaluated using electrospray ionization mass spectrometry (ESI-MS), demonstrating selectivity for the first structure. The interaction pattern of the ligand with G-quadruplex was investigated by molecular docking and stacking was found to be the preferred binding mode.
Keywords: Sonogashira reaction; A3 coupling; anthracene; G-quadruplex; mass spectrometry; molecular modeling Sonogashira reaction; A3 coupling; anthracene; G-quadruplex; mass spectrometry; molecular modeling
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MDPI and ACS Style

Ribaudo, G.; Ongaro, A.; Oselladore, E.; Zagotto, G.; Memo, M.; Gianoncelli, A. 9,10-Bis[(4-(2-hydroxyethyl)piperazine-1-yl)prop-2-yne-1-yl]anthracene: Synthesis and G-quadruplex Selectivity. Molbank 2020, 2020, M1138.

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