2026-04-19T16:33:20Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/70852022-10-07T00:05:15Zcom_10259_3924com_10259_5086com_10259_2604col_10259_3925

Picci, Giacomo Carreira Barral, Israel Alonso Carrillo, Daniel Busonera, Chiara Milia, Jessica Quesada Pato, Roberto Caltagirone, Claudia 2022-10-06T09:29:20Z 2022-10-06T09:29:20Z 2022-09 1477-0520 http://hdl.handle.net/10259/7085 10.1039/D2OB01444K 1477-0539 A new family of squaramide-based anionophores (L1–L8) have been synthesised and fully characterised with the aim to investigate the effect of indolyl substituents on their anion binding and transmembrane transport properties. L1, L2, L6, and L8, bearing a 7-indolyl/indol-7-yl moiety as the substituent, were found to be the most efficient of the series in binding chloride with high stability constants. L1, L6, and L8 were also found to be the most potent anionophores of the series, able to mediate transmembrane anion transport. In particular, L6 bearing the 3,5-bis(trifluoromethyl)phenyl group was found to be the most active transporter, and its efficiency as an anionophore/anion transporter was favourably compared with that of their symmetrically-substituted squaramide analogues L9 and L10, previously reported in the literature. Consejería de Educación de la Junta de Castilla y León (project BU067P20) and the Ministerio de Ciencia e Innovación (project PID2020-117610RB-I00). I. C.-B. and D. A.-C. thank the Consejería de Educación de la Junta de Castilla y León, the European Social Fund (ESF) and the European Regional Development Fund (ERDF) for their post-doctoral (I. C.-B.) and pre-doctoral (D. A.-C.) contracts. The authors gratefully acknowledge Andrea Sancho-Medina for her contributions to transmembrane anion transport experiments. Financial support from MIUR (PRIN 2017 project 2017EKCS35) is gratefully acknowledged by C. C. and G. P. along with the Università degli Studi di Cagliari (FIR 2016-2019) and the Fondazione di Sardegna (FdS Progetti Biennali di Ateneo, annualità 2020, project F75F21001260007). application/pdf eng Royal Society of Chemistry Organic & Biomolecular Chemistry. 2022, https://doi.org/10.1039/D2OB01444K info:eu-repo/grantAgreement/Junta de Castilla y León//BU067P20 info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-117610RB-I00/ES/SMALL MOLECULE TRANSMEMBRANE ANION CARRIERS FOR BIOLOGICAL APPLICATIONS info:eu-repo/grantAgreement/MIUR//2017EKCS35 info:eu-repo/grantAgreement/Università degli Studi di Cagliari//FIR 2016-2019 info:eu-repo/grantAgreement/Fondazione di Sardegna//F75F21001260007 Attribution-NonCommercial 3.0 Unported http://creativecommons.org/licenses/by-nc/3.0/ info:eu-repo/semantics/openAccess Química orgánica Bioquímica Chemistry, Organic Biochemistry The role of indolyl substituents in squaramide-based anionophores info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Organic & Biomolecular Chemistry