2026-04-23T00:08:24Zhttps://riubu.ubu.es/oai/requestoai:riubu.ubu.es:10259/56772022-11-21T12:04:43Zcom_10259_4354com_10259_5086com_10259_2604com_10259_4363com_10259_4365col_10259_4355col_10259_4364col_10259_4366
Busto Vázquez, Natalia
83
500
García Calvo, José
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500
Cuevas Vicario, José Vicente
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0000-0002-2421-1529
Herrera, Antonio
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Mergny, Jean-Louis
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Pons, Sebastian
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Torroba Pérez, Tomás
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García Ruiz, Begoña
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2021-04-05T11:46:16Z
2021-04-05T11:46:16Z
2021-03
0045-2068
http://hdl.handle.net/10259/5677
10.1016/j.bioorg.2021.104660
A structure–activity relationship (SAR) study in terms of G-quadruplex binding ability and antiproliferative activity of six fluorescent perylenemonoimide (PMIs) derivatives is reported. A positive charge seems to be the key to target G4. This study also reveals the importance of the element substitution in the potential biological activity of PMIs, being the polyethylene glycol (PEG) chains in the peri position responsible for their antiproliferative activity. Among them, the cationic PMI6 with two PEG chains is the most promising compound since its fluorescence is enhanced in the presence of G-quadruplex structures. Moreover, PMI6 binds to the human telomeric G-quadruplex hTelo with high affinity and displays a high antiproliferative potential towards HeLa (cervical adenocarcinoma), A549 (lung adenocarcinoma) and A2780 (ovarian adenocarcinoma) cells. Its fate can be followed inside cells thanks to its fluorescent properties: the compound is found to accumulate in the mitochondria.
“la Caixa” Foundation (LCF/PR/PR12/11070003), Ministerio de Ciencia, Innovación y Universidades-FEDER (RTI2018-102040-B-100), Junta de Castilla y León-FEDER (BU305P18 and BU263P18) is gratefully acknowledged. N.B. is grateful to Aurore Guédin of the ARNA Laboratory for technical support and also to the financial support of the José Castillejo Program by the Spanish Ministry of Education, Culture and Sports (JC2015-00403). A.H. was funded by a Juan de la Cierva fellowship (FJCI-2015-26175) from the Ministerio de Economía y Competitividad. This research has made use of the high-performance computing resources of the Castilla y León Supercomputing Center (SCAYLE, https://www.scayle.es), financed by FEDER (Fondo Europeo de Desarrollo Regional). Networking support of NECTAR COST Action CA18202 is fully acknowledged. This work was supported by the SYMBIT project (reg. no. CZ.02.1.01/0.0/0.0/15_003/0000477) financed by the ERDF.
application/pdf
eng
Elsevier
Bioorganic Chemistry. 2021, V. 108, 104660
https://doi.org/10.1016/j.bioorg.2021.104660
info:eu-repo/grantAgreement/FundaciónLaCaixa/LCF/PR/PR12/11070003
info:eu-repo/grantAgreement/MICINN/RTI2018-102040-B-100
info:eu-repo/grantAgreement/JCyL/BU305P18
info:eu-repo/grantAgreement/JCyL/BU263P18
Attribution-NonCommercial-NoDerivatives 4.0 Internacional
http://creativecommons.org/licenses/by-nc-nd/4.0/
info:eu-repo/semantics/openAccess
G-quadruplexes
Antiproliferative
Perylenemonoimide
DNA binding
Química física
Química orgánica
Química inorgánica
Chemistry, Physical and theoretical
Chemistry, Organic
Chemistry, Inorganic
Influence of core extension and side chain nature in targeting G-quadruplex structures with perylene monoimide derivatives
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Bioorganic Chemistry
108
104660
TEXT
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2022-11-21 13:04:43.748
Repositorio Institucional de la Universidad de Burgos
bubrep@ubu.es
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