2026-08-22T22:58:17Zhttps://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 Carreira Barral, Israel García Valverde, María Quesada Pato, Roberto 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