Roseophilin-inspired derivatives as transmembrane anion carriers

Roseophilin is an alkaloid structurally related to prodiginines . The intriguing pharmacological properties of these derivatives have prompted us to prepare synthetic compounds 1–3 inspired by their structure and to explore their transmembrane anion transport activity. The methoxyfuran heterocycle i...

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Autores: Díaz Cabrera, Sandra, Carreira Barral, Israel, García Valverde, María, Quesada Pato, Roberto
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2022
País:España
Institución:Universidad de Burgos (UBU)
Repositorio:Repositorio Institucional de la Universidad de Burgos (RIUBU)
OAI Identifier:oai:riubu.ubu.es:10259/8354
Acceso en línea:http://hdl.handle.net/10259/8354
Access Level:acceso abierto
Palabra clave:Supramolecular chemistry
Ionophores
Alkaloids
Roseophilin
Vesicles
Anion transport
Química orgánica
Chemistry, Organic
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spelling Roseophilin-inspired derivatives as transmembrane anion carriersDíaz Cabrera, SandraCarreira Barral, IsraelGarcía Valverde, MaríaQuesada Pato, RobertoSupramolecular chemistryIonophoresAlkaloidsRoseophilinVesiclesAnion transportQuímica orgánicaChemistry, OrganicRoseophilin is an alkaloid structurally related to prodiginines . The intriguing pharmacological properties of these derivatives have prompted us to prepare synthetic compounds 1–3 inspired by their structure and to explore their transmembrane anion transport activity. The methoxyfuran heterocycle impacts the anionophoric activity of the compounds as a result of the reduced hydrogen-bonding ability and electrostatic repulsions between the oxygen in the furan ring and the anions. The position of the furan was also found to be crucial for determining their anion transport activity. Overall, replacement of the characteristic methoxypyrrole moiety of prodiginines and tambjamines by the methoxyfuran found in roseophilin is detrimental to their ability as anion carriers, suggesting that the biological activity of roseophilin is likely not related to their potential activity as anion carriers. Compound 2, bearing a furan ring attached to a dipyrromethene moiety, was found to be the most active anion carrier.We would like to thank funding from Consejería de Educación de la Junta de Castilla y León and ERDF (project BU067P20) and MCIN/AEI/10.13039/501100011033 (grant PID2020-117610RB-100). S.D.-C. and I. C.-B. thank Consejería de Educación de la Junta de Castilla y León, ERDF (European Regional Development Fund) and European Social Fund for their predoctoral (S. D.-C.) and postdoctoral (I. C.-B.) contracts.Taylor and Francis202420242022info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttp://hdl.handle.net/10259/8354reponame:Repositorio Institucional de la Universidad de Burgos (RIUBU)instname:Universidad de Burgos (UBU)InglésSupramolecular Chemistry. 2022, V. 33, n. 9, p. 550-558https://doi.org/10.1080/10610278.2022.2099277Atribución-NoComercial 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc/4.0/info:eu-repo/semantics/openAccessoai:riubu.ubu.es:10259/83542026-05-28T07:56:11Z
dc.title.none.fl_str_mv Roseophilin-inspired derivatives as transmembrane anion carriers
title Roseophilin-inspired derivatives as transmembrane anion carriers
spellingShingle Roseophilin-inspired derivatives as transmembrane anion carriers
Díaz Cabrera, Sandra
Supramolecular chemistry
Ionophores
Alkaloids
Roseophilin
Vesicles
Anion transport
Química orgánica
Chemistry, Organic
title_short Roseophilin-inspired derivatives as transmembrane anion carriers
title_full Roseophilin-inspired derivatives as transmembrane anion carriers
title_fullStr Roseophilin-inspired derivatives as transmembrane anion carriers
title_full_unstemmed Roseophilin-inspired derivatives as transmembrane anion carriers
title_sort Roseophilin-inspired derivatives as transmembrane anion carriers
dc.creator.none.fl_str_mv Díaz Cabrera, Sandra
Carreira Barral, Israel
García Valverde, María
Quesada Pato, Roberto
author Díaz Cabrera, Sandra
author_facet Díaz Cabrera, Sandra
Carreira Barral, Israel
García Valverde, María
Quesada Pato, Roberto
author_role author
author2 Carreira Barral, Israel
García Valverde, María
Quesada Pato, Roberto
author2_role author
author
author
dc.subject.none.fl_str_mv Supramolecular chemistry
Ionophores
Alkaloids
Roseophilin
Vesicles
Anion transport
Química orgánica
Chemistry, Organic
topic Supramolecular chemistry
Ionophores
Alkaloids
Roseophilin
Vesicles
Anion transport
Química orgánica
Chemistry, Organic
description Roseophilin is an alkaloid structurally related to prodiginines . The intriguing pharmacological properties of these derivatives have prompted us to prepare synthetic compounds 1–3 inspired by their structure and to explore their transmembrane anion transport activity. The methoxyfuran heterocycle impacts the anionophoric activity of the compounds as a result of the reduced hydrogen-bonding ability and electrostatic repulsions between the oxygen in the furan ring and the anions. The position of the furan was also found to be crucial for determining their anion transport activity. Overall, replacement of the characteristic methoxypyrrole moiety of prodiginines and tambjamines by the methoxyfuran found in roseophilin is detrimental to their ability as anion carriers, suggesting that the biological activity of roseophilin is likely not related to their potential activity as anion carriers. Compound 2, bearing a furan ring attached to a dipyrromethene moiety, was found to be the most active anion carrier.
publishDate 2022
dc.date.none.fl_str_mv 2022
2024
2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10259/8354
url http://hdl.handle.net/10259/8354
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Supramolecular Chemistry. 2022, V. 33, n. 9, p. 550-558
https://doi.org/10.1080/10610278.2022.2099277
dc.rights.none.fl_str_mv Atribución-NoComercial 4.0 Internacional
http://creativecommons.org/licenses/by-nc/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Atribución-NoComercial 4.0 Internacional
http://creativecommons.org/licenses/by-nc/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Taylor and Francis
publisher.none.fl_str_mv Taylor and Francis
dc.source.none.fl_str_mv reponame:Repositorio Institucional de la Universidad de Burgos (RIUBU)
instname:Universidad de Burgos (UBU)
instname_str Universidad de Burgos (UBU)
reponame_str Repositorio Institucional de la Universidad de Burgos (RIUBU)
collection Repositorio Institucional de la Universidad de Burgos (RIUBU)
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,301603

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