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

1
Department of Molecular and Translational Medicine, University of Brescia, 25121 Brescia, Italy
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Department of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131 Padova, Italy
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Author to whom correspondence should be addressed.
Molbank 2020, 2020(2), M1138; https://doi.org/10.3390/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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