One-step template-directed synthesis of acridine-based rigid cyclophanes

Cyclo-bisintercalands are macrocyclic systems containing aromatic subunits, which are commonly used as hosts for aromatic molecules and as DNA intercalators. In this article, a step-by-step synthesis of a series of cyclo-bisintercalands containing 3,6-diaminoacridines as aromatic units, and connecte...

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Detalhes bibliográficos
Autores: Sierra Tornero, Sara, Duskova, Katerina|||0000-0003-4500-186X, Fernández Domínguez, María José, Gude Rodríguez, Lourdes|||0000-0002-0220-3755, Lorente Pérez, Antonio
Formato: artículo
Fecha de publicación:2012
País:España
Recursos:Universidad de Alcalá (UAH)
Repositorio:e_Buah Biblioteca Digital Universidad de Alcalá
Idioma:inglés
OAI Identifier:oai:ebuah.uah.es:10017/65013
Acesso em linha:http://hdl.handle.net/10017/65013
https://dx.doi.org/10.1016/j.tet.2012.08.003
Access Level:acceso abierto
Palavra-chave:Cyclophanes
Template effect
Acridine
Cyclo-bisintercalands
Química
Chemistry
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spelling One-step template-directed synthesis of acridine-based rigid cyclophanesSierra Tornero, SaraDuskova, Katerina|||0000-0003-4500-186XFernández Domínguez, María JoséGude Rodríguez, Lourdes|||0000-0002-0220-3755Lorente Pérez, AntonioCyclophanesTemplate effectAcridineCyclo-bisintercalandsQuímicaChemistryCyclo-bisintercalands are macrocyclic systems containing aromatic subunits, which are commonly used as hosts for aromatic molecules and as DNA intercalators. In this article, a step-by-step synthesis of a series of cyclo-bisintercalands containing 3,6-diaminoacridines as aromatic units, and connected by rigid spacers of different lengths, is reported. In addition, we describe herein a more efficient synthetic alternative, involving single-step template-directed processes. The new routes allow the easy synthetic access to these macrocyclic systems with acceptable yields. The synthesized cyclo-bisintercalands and their precursors have been structurally characterized by UV-visible and NMR methods. Preliminary biological activity assays performed on the bis- and cyclo-bisintercalands revealed interesting cytotoxic properties against different tumor cell lines, especially in the case of the bisintercalands, highlighting their potential as cancer chemotherapeutic agents.Comunidad de MadridUniversidad de AlcaláMinisterio de Ciencia e InnovaciónPharmaMar20122012-10-21journal articlehttp://purl.org/coar/resource_type/c_6501NAhttp://purl.org/coar/version/c_be7fb7dd8ff6fe43info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10017/65013https://dx.doi.org/10.1016/j.tet.2012.08.003reponame:e_Buah Biblioteca Digital Universidad de Alcaláinstname:Universidad de Alcalá (UAH)InglésengComunidad de Madrid http://dx.doi.org/10.13039/100012818 Not available CCG10-UAH%2FPPQ-5961Ministerio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 Not available CTQ2011-26822open accesshttp://purl.org/coar/access_right/c_abf2Attribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:ebuah.uah.es:10017/650132026-06-18T11:13:07Z
dc.title.none.fl_str_mv One-step template-directed synthesis of acridine-based rigid cyclophanes
title One-step template-directed synthesis of acridine-based rigid cyclophanes
spellingShingle One-step template-directed synthesis of acridine-based rigid cyclophanes
Sierra Tornero, Sara
Cyclophanes
Template effect
Acridine
Cyclo-bisintercalands
Química
Chemistry
title_short One-step template-directed synthesis of acridine-based rigid cyclophanes
title_full One-step template-directed synthesis of acridine-based rigid cyclophanes
title_fullStr One-step template-directed synthesis of acridine-based rigid cyclophanes
title_full_unstemmed One-step template-directed synthesis of acridine-based rigid cyclophanes
title_sort One-step template-directed synthesis of acridine-based rigid cyclophanes
dc.creator.none.fl_str_mv Sierra Tornero, Sara
Duskova, Katerina|||0000-0003-4500-186X
Fernández Domínguez, María José
Gude Rodríguez, Lourdes|||0000-0002-0220-3755
Lorente Pérez, Antonio
author Sierra Tornero, Sara
author_facet Sierra Tornero, Sara
Duskova, Katerina|||0000-0003-4500-186X
Fernández Domínguez, María José
Gude Rodríguez, Lourdes|||0000-0002-0220-3755
Lorente Pérez, Antonio
author_role author
author2 Duskova, Katerina|||0000-0003-4500-186X
Fernández Domínguez, María José
Gude Rodríguez, Lourdes|||0000-0002-0220-3755
Lorente Pérez, Antonio
author2_role author
author
author
author
dc.subject.none.fl_str_mv Cyclophanes
Template effect
Acridine
Cyclo-bisintercalands
Química
Chemistry
topic Cyclophanes
Template effect
Acridine
Cyclo-bisintercalands
Química
Chemistry
description Cyclo-bisintercalands are macrocyclic systems containing aromatic subunits, which are commonly used as hosts for aromatic molecules and as DNA intercalators. In this article, a step-by-step synthesis of a series of cyclo-bisintercalands containing 3,6-diaminoacridines as aromatic units, and connected by rigid spacers of different lengths, is reported. In addition, we describe herein a more efficient synthetic alternative, involving single-step template-directed processes. The new routes allow the easy synthetic access to these macrocyclic systems with acceptable yields. The synthesized cyclo-bisintercalands and their precursors have been structurally characterized by UV-visible and NMR methods. Preliminary biological activity assays performed on the bis- and cyclo-bisintercalands revealed interesting cytotoxic properties against different tumor cell lines, especially in the case of the bisintercalands, highlighting their potential as cancer chemotherapeutic agents.
publishDate 2012
dc.date.none.fl_str_mv 2012
2012-10-21
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
NA
http://purl.org/coar/version/c_be7fb7dd8ff6fe43
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10017/65013
https://dx.doi.org/10.1016/j.tet.2012.08.003
url http://hdl.handle.net/10017/65013
https://dx.doi.org/10.1016/j.tet.2012.08.003
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Comunidad de Madrid http://dx.doi.org/10.13039/100012818 Not available CCG10-UAH%2FPPQ-5961
Ministerio de Ciencia e Innovación http://dx.doi.org/10.13039/501100004837 Not available CTQ2011-26822
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:e_Buah Biblioteca Digital Universidad de Alcalá
instname:Universidad de Alcalá (UAH)
instname_str Universidad de Alcalá (UAH)
reponame_str e_Buah Biblioteca Digital Universidad de Alcalá
collection e_Buah Biblioteca Digital Universidad de Alcalá
repository.name.fl_str_mv
repository.mail.fl_str_mv
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