2026-04-19T17:03:13Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/83542024-01-16T13:29:03Zcom_10259_3592com_10259_3591com_10259.4_106com_10259_2604com_10259_3924com_10259_5086col_10259_3930col_10259_3925

Díaz Cabrera, Sandra fc3916df-6abf-4744-a527-397631146729 600 Carreira Barral, Israel 763 600 0000-0002-4835-8752 García Valverde, María 222 600 0000-0002-3990-8388 Quesada Pato, Roberto 458 600 0000-0003-2764-7157 2024-01-16T13:22:05Z 2024-01-16T13:22:05Z 2022 1061-0278 http://hdl.handle.net/10259/8354 10.1080/10610278.2022.2099277 1029-0478 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. 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. application/pdf eng Taylor and Francis Supramolecular Chemistry. 2022, V. 33, n. 9, p. 550-558 https://doi.org/10.1080/10610278.2022.2099277 Atribución-NoComercial 4.0 Internacional http://creativecommons.org/licenses/by-nc/4.0/ info:eu-repo/semantics/openAccess Supramolecular chemistry Ionophores Alkaloids Roseophilin Vesicles Anion transport Química orgánica Chemistry, Organic Roseophilin-inspired derivatives as transmembrane anion carriers info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion Supramolecular Chemistry 33 9 550 558 LICENSE license.txt license.txt text/plain; charset=utf-8 999 https://riubu.ubu.es/bitstream/10259/8354/3/license.txt b295bcbce42e2caabeb0c623d3860c06 MD5 3 CC-LICENSE license_rdf license_rdf application/rdf+xml; charset=utf-8 914 https://riubu.ubu.es/bitstream/10259/8354/2/license_rdf 24013099e9e6abb1575dc6ce0855efd5 MD5 2 ORIGINAL Díaz-sc_2022.docx Díaz-sc_2022.docx application/vnd.openxmlformats-officedocument.wordprocessingml.document 368406 https://riubu.ubu.es/bitstream/10259/8354/1/D%c3%adaz-sc_2022.docx a8f3a970f3b0a1e9ea80efceec36a50c MD5 1 10259/8354 oai:riubu.ubu.es:10259/8354 2024-01-16 14:29:03.535 Repositorio Institucional de la Universidad de Burgos bubrep@ubu.es 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