Roseophilin-inspired derivatives as transmembrane anion carriers

ABSTRACT

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.

GRAPHICAL ABSTRACT

KEYWORDS:

• Supramolecular chemistry
• ionophores
• alkaloids
• roseophilin
• vesicles
• anion transport

Acknowledgments

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. We also thank Andrea Sancho-Medina for her technical assistance.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Supplementary material

Supplemental data for this article can be accessed online at https://doi.org/10.1080/10610278.2022.2099277

Additional information

Funding

This work was supported by Consejería de Educación, Junta de Castilla y León and European Regional Development Fund [BU067P20]; and MCIN/AEI/10.13039/501100011033 [PID2020-117610RB-100].