RT info:eu-repo/semantics/article
T1 Roseophilin-inspired derivatives as transmembrane anion carriers
A1 Díaz Cabrera, Sandra
A1 Carreira Barral, Israel
A1 García Valverde, María
A1 Quesada Pato, Roberto
K1 Supramolecular chemistry
K1 Ionophores
K1 Alkaloids
K1 Roseophilin
K1 Vesicles
K1 Anion transport
K1 Química orgánica
K1 Chemistry, Organic
AB 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.
PB Taylor and Francis
SN 1061-0278
YR 2022
FD 2022
LK http://hdl.handle.net/10259/8354
UL http://hdl.handle.net/10259/8354
LA eng
NO 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.
DS Repositorio Institucional de la Universidad de Burgos
RD 09-may-2024