TY - JOUR
T1 - Rational Design of Supramolecular Receptors for Consistent Binding Affinities under High-Salinity Conditions
AU - Gómez-González, Borja
AU - Basílio, Nuno
AU - Vaz, Belén
AU - Paleo, M. Rita
AU - Sardina, F. Javier
AU - Pérez-Lorenzo, Moisés
AU - García-Río, Luis
N1 - info:eu-repo/grantAgreement/FCT/Concurso para Atribuição do Estatuto e Financiamento de Laboratórios Associados (LA)/LA%2FP%2F0008%2F2020/PT#
info:eu-repo/grantAgreement/FCT/Concurso de avaliação no âmbito do Programa Plurianual de Financiamento de Unidades de I&D (2017%2F2018) - Financiamento Programático/UIDP%2F50006%2F2020/PT#
info:eu-repo/grantAgreement/FCT/Concurso de avaliação no âmbito do Programa Plurianual de Financiamento de Unidades de I&D (2017%2F2018) - Financiamento Base/UIDB%2F50006%2F2020/PT#
Funding Information:
This work was funded by Xunta de Galicia (Centro Singular de Investigación de Galicia-Accreditation 2019-2022 ED431G 2019/06, ED431C 2022/24, ED431C 2021/45, and 001_IN853D_2022) and Associate Laboratory for Green Chemistry-LAQV (LA/P/0008/2020 DOI: 10.54499/LA/P/0008/2020, UIDP/50006/2020 DOI: 10.54499/UIDP/50006/2020, and UIDB/50006/2020 DOI: 10.54499/UIDB/50006/2020). F.J.S. and L.G.R. acknowledge the founding of the Mestrelab Research Center (CIM) through the support of the Galician Innovation Agency (GAIN).
Publisher Copyright:
© 2025 American Chemical Society.
PY - 2025/4/17
Y1 - 2025/4/17
N2 - The development of water-soluble multicharged macrocycles has opened promising pathways in biomedical applications, enabling selective molecular recognition for therapeutic and diagnostic uses. Yet, traditional polyanionic and polycationic receptors often face performance limitations under realistic operating conditions. A major drawback is the natural tendency of these polycharged hosts to experience increasing screening effects as concentration rises due to self-ion pairing phenomena, which can reduce binding efficiency by several orders of magnitude. These issues are further intensified when polyionic receptors are used in high-salinity environments, typically used to replicate physiological settings, where the abundance of ions introduces additional screening effects that diminish the supramolecular affinity for a wide range of guests. This study presents a new approach that leverages zwitterionic synthetic receptors with rationally engineered architectures to overcome these challenges. By incorporation of specific structural features, self-ion pairing is eliminated, effectively making host concentration no longer a controlling factor in the thermodynamics of the complexation process. Additionally, these dual-charged hosts achieve self-contained stabilization, naturally shielding recognition sites from external ion interference under high-salinity conditions. Furthermore, the ability of these supramolecular hosts to encapsulate zwitterionic guests, a challenging task due to the strong solvation of these molecules in aqueous solution, adds significant value to the functional versatility of these macrocycles. Altogether, these findings represent a significant advancement in the design of stable and adaptable receptor systems for complex environments.
AB - The development of water-soluble multicharged macrocycles has opened promising pathways in biomedical applications, enabling selective molecular recognition for therapeutic and diagnostic uses. Yet, traditional polyanionic and polycationic receptors often face performance limitations under realistic operating conditions. A major drawback is the natural tendency of these polycharged hosts to experience increasing screening effects as concentration rises due to self-ion pairing phenomena, which can reduce binding efficiency by several orders of magnitude. These issues are further intensified when polyionic receptors are used in high-salinity environments, typically used to replicate physiological settings, where the abundance of ions introduces additional screening effects that diminish the supramolecular affinity for a wide range of guests. This study presents a new approach that leverages zwitterionic synthetic receptors with rationally engineered architectures to overcome these challenges. By incorporation of specific structural features, self-ion pairing is eliminated, effectively making host concentration no longer a controlling factor in the thermodynamics of the complexation process. Additionally, these dual-charged hosts achieve self-contained stabilization, naturally shielding recognition sites from external ion interference under high-salinity conditions. Furthermore, the ability of these supramolecular hosts to encapsulate zwitterionic guests, a challenging task due to the strong solvation of these molecules in aqueous solution, adds significant value to the functional versatility of these macrocycles. Altogether, these findings represent a significant advancement in the design of stable and adaptable receptor systems for complex environments.
UR - https://www.scopus.com/pages/publications/105003037444
UR - https://www.webofscience.com/wos/woscc/full-record/WOS:001469206800001
U2 - 10.1021/acs.joc.5c00068
DO - 10.1021/acs.joc.5c00068
M3 - Article
C2 - 40245266
AN - SCOPUS:105003037444
SN - 0022-3263
VL - 90
SP - 6134
EP - 6145
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 18
ER -