9,10-Bis[(4-(2-hydroxyethyl)piperazine-1-yl)prop-2-yne-1-yl]anthracene: Synthesis and G-quadruplex Selectivity
G-quadruplex DNA is the target of several natural and synthetic small molecules with antiproliferative and antiviral activity. We here report the synthesis through <i>Sonogashira</i> reaction and A3 coupling of a disubstituted anthracene derivative, 9,10-bis[(4-(2-hydroxyethyl)piperazine...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-05-01
|
| Series: | Molbank |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1422-8599/2020/2/M1138 |
| id |
doaj-15062b44892344bcbad555ecf6c2b3ca |
|---|---|
| record_format |
Article |
| spelling |
doaj-15062b44892344bcbad555ecf6c2b3ca2020-11-25T03:10:00ZengMDPI AGMolbank1422-85992020-05-012020M1138M113810.3390/M11389,10-Bis[(4-(2-hydroxyethyl)piperazine-1-yl)prop-2-yne-1-yl]anthracene: Synthesis and G-quadruplex SelectivityGiovanni Ribaudo0Alberto Ongaro1Erika Oselladore2Giuseppe Zagotto3Maurizio Memo4Alessandra Gianoncelli5Department of Molecular and Translational Medicine, University of Brescia, 25121 Brescia, ItalyDepartment of Molecular and Translational Medicine, University of Brescia, 25121 Brescia, ItalyDepartment of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131 Padova, ItalyDepartment of Pharmaceutical and Pharmacological Sciences, University of Padova, 35131 Padova, ItalyDepartment of Molecular and Translational Medicine, University of Brescia, 25121 Brescia, ItalyDepartment of Molecular and Translational Medicine, University of Brescia, 25121 Brescia, ItalyG-quadruplex DNA is the target of several natural and synthetic small molecules with antiproliferative and antiviral activity. We here report the synthesis through <i>Sonogashira</i> 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.https://www.mdpi.com/1422-8599/2020/2/M1138<i>Sonogashira</i> reactionA3 couplinganthraceneG-quadruplexmass spectrometrymolecular modeling |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Giovanni Ribaudo Alberto Ongaro Erika Oselladore Giuseppe Zagotto Maurizio Memo Alessandra Gianoncelli |
| spellingShingle |
Giovanni Ribaudo Alberto Ongaro Erika Oselladore Giuseppe Zagotto Maurizio Memo Alessandra Gianoncelli 9,10-Bis[(4-(2-hydroxyethyl)piperazine-1-yl)prop-2-yne-1-yl]anthracene: Synthesis and G-quadruplex Selectivity Molbank <i>Sonogashira</i> reaction A3 coupling anthracene G-quadruplex mass spectrometry molecular modeling |
| author_facet |
Giovanni Ribaudo Alberto Ongaro Erika Oselladore Giuseppe Zagotto Maurizio Memo Alessandra Gianoncelli |
| author_sort |
Giovanni Ribaudo |
| title |
9,10-Bis[(4-(2-hydroxyethyl)piperazine-1-yl)prop-2-yne-1-yl]anthracene: Synthesis and G-quadruplex Selectivity |
| title_short |
9,10-Bis[(4-(2-hydroxyethyl)piperazine-1-yl)prop-2-yne-1-yl]anthracene: Synthesis and G-quadruplex Selectivity |
| title_full |
9,10-Bis[(4-(2-hydroxyethyl)piperazine-1-yl)prop-2-yne-1-yl]anthracene: Synthesis and G-quadruplex Selectivity |
| title_fullStr |
9,10-Bis[(4-(2-hydroxyethyl)piperazine-1-yl)prop-2-yne-1-yl]anthracene: Synthesis and G-quadruplex Selectivity |
| title_full_unstemmed |
9,10-Bis[(4-(2-hydroxyethyl)piperazine-1-yl)prop-2-yne-1-yl]anthracene: Synthesis and G-quadruplex Selectivity |
| title_sort |
9,10-bis[(4-(2-hydroxyethyl)piperazine-1-yl)prop-2-yne-1-yl]anthracene: synthesis and g-quadruplex selectivity |
| publisher |
MDPI AG |
| series |
Molbank |
| issn |
1422-8599 |
| publishDate |
2020-05-01 |
| description |
G-quadruplex DNA is the target of several natural and synthetic small molecules with antiproliferative and antiviral activity. We here report the synthesis through <i>Sonogashira</i> 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. |
| topic |
<i>Sonogashira</i> reaction A3 coupling anthracene G-quadruplex mass spectrometry molecular modeling |
| url |
https://www.mdpi.com/1422-8599/2020/2/M1138 |
| work_keys_str_mv |
AT giovanniribaudo 910bis42hydroxyethylpiperazine1ylprop2yne1ylanthracenesynthesisandgquadruplexselectivity AT albertoongaro 910bis42hydroxyethylpiperazine1ylprop2yne1ylanthracenesynthesisandgquadruplexselectivity AT erikaoselladore 910bis42hydroxyethylpiperazine1ylprop2yne1ylanthracenesynthesisandgquadruplexselectivity AT giuseppezagotto 910bis42hydroxyethylpiperazine1ylprop2yne1ylanthracenesynthesisandgquadruplexselectivity AT mauriziomemo 910bis42hydroxyethylpiperazine1ylprop2yne1ylanthracenesynthesisandgquadruplexselectivity AT alessandragianoncelli 910bis42hydroxyethylpiperazine1ylprop2yne1ylanthracenesynthesisandgquadruplexselectivity |
| _version_ |
1724661147122008064 |