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The Red Cage: Implementation of pH-Responsiveness Within a Macrobicyclic Pyridinium-Based Molecular Host

dc.contributor.authorCortón, Pablo
dc.contributor.authorWang, Hongye
dc.contributor.authorNeira, Iago
dc.contributor.authorBlanco-Gómez, Arturo
dc.contributor.authorPazos, Elena
dc.contributor.authorPeinador, Carlos
dc.contributor.authorLi, Hao
dc.contributor.authorGarcía, Marcos D.
dc.date.accessioned2022-09-21T09:02:23Z
dc.date.issued2021-11-09
dc.identifier.citationP. Cortón, H. Wang, I. Neira, A. Blanco-Gómez, E. Pazos, C. Peinador, H. Li and M. D. García, “The red cage”: implementation of pH-responsiveness within a macrobicyclic pyridinium-based molecular host, Org. Chem. Front., 2021, 9, 81–87. https://doi.org/10.1039/D1QO01331Aes_ES
dc.identifier.issn2052-4129
dc.identifier.urihttp://hdl.handle.net/2183/31673
dc.description.abstract[Abstract] We present herein the implementation of pH-responsiveness into a new polycationic macrobicyclic structure, namely what we have termed the “red cage”. The hydrolytically-stable cryptand-like compound has been prepared in a relatively high yield in aqueous media by a kinetically-controlled hydrazone-exchange reaction, promoted by the unusual high stability of the new hydrazone C[double bond, length as m-dash]N bonds formed. In organic media the macrobicycle was found not able to complex model aromatic substrates. In buffered aqueous solutions, as a comparison, the “red cage” was found able to recognize them, but the binding was observed to be more efficient in acidic form of the cyclophane compared with its conjugate base.es_ES
dc.description.sponsorshipWe are thankful for the funding received from the Agencia Estatal de Investigación and FEDER (PID2019-105272GB-I00 and CTQ2017-89166-R), the Xunta de Galicia (ED431C 2018/39 and 508/2020), and the European Research Council (grant agreement no. 851179). I. N. and P. C. thank, respectively, the MECD (FPU program, FPU2016/02347) and Xunta de Galicia (Axudas de Apoio á Etapa de Formación Predoutoral, ED481A-2020/019) for financial support. A. B. G. thanks Xunta de Galicia for a Postdoctoral Fellowship (ED481B-2021-099). E. P. thanks the Agencia Estatal de Investigación for her Ramón y Cajal contract (RYC2019-027199-I). H. Li wants to thank the financial supports from the National Natural Science Foundation of China (no. 91856116, 21772173, and 21922108), and the Natural Science Foundation of Zhejiang Province (no. LR18B020001). The authors are deeply grateful to professor Jonathan L. Sessler, for promoting and encouraging the collaboration reported herein: "we should be competing with Mother Nature to extract her secrets, not with one another!"es_ES
dc.description.sponsorshipXunta de Galicia; ED431C 2018/39es_ES
dc.description.sponsorshipXunta de Galicia; ED431C 508/2020es_ES
dc.description.sponsorshipXunta de Galicia; ED481A-2020/019es_ES
dc.description.sponsorshipXunta de Galicia; ED481B-2021-099es_ES
dc.description.sponsorshipChina. National Natural Science Foundation of China; 91856116es_ES
dc.description.sponsorshipChina. National Natural Science Foundation of China; 21772173es_ES
dc.description.sponsorshipChina. National Natural Science Foundation of China; 21922108es_ES
dc.description.sponsorshipChina. Natural Science Foundation of Zhejiang Province; LR18B020001es_ES
dc.language.isoenges_ES
dc.publisherRoyal Society of Chemistryes_ES
dc.relationinfo:eu-repo/grantAgreement/EC/H2020/851179es_ES
dc.relationinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-105272GB-I00/ES/DESARROLLO DE NUEVOS CICLOFANOS AUTOENSAMBLADOS Y SU IMPLEMENTACION EN ESTRUCTURAS NANOMETRICAS/
dc.relationinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-89166-R/ES/HERRAMIENTAS PEPTIDICAS PARA APLICACIONES BIOLOGICAS: SENSORES INTELIGENTES PARA ESTUDIAR NITRACION DE PROTEINAS Y NANOMATERIALES CON FUNCIONALIDADES MODULABLES/
dc.relationinfo:eu-repo/grantAgreement/MECD/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/FPU16%2F02347/ES/
dc.relationinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RYC2019-027199-I/ES/
dc.relation.urihttps://doi.org/10.1039/D1QO01331Aes_ES
dc.titleThe Red Cage: Implementation of pH-Responsiveness Within a Macrobicyclic Pyridinium-Based Molecular Hostes_ES
dc.typeinfo:eu-repo/semantics/articlees_ES
dc.rights.accessinfo:eu-repo/semantics/embargoedAccesses_ES
dc.date.embargoEndDate2022-11-09es_ES
dc.date.embargoLift2022-11-09
UDC.journalTitleOrganic Chemistry Frontierses_ES
UDC.volume9es_ES
UDC.issue1es_ES
UDC.startPage81es_ES
UDC.endPage87es_ES
dc.identifier.doi10.1039/D1QO01331A


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