Substituent effects of fluorinated bambusurils on their anion transport

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F25%3A00141662" target="_blank" >RIV/00216224:14310/25:00141662 - isvavai.cz</a>

Výsledek na webu

<a href="https://pubs.rsc.org/en/content/articlelanding/2025/ob/d5ob00400d" target="_blank" >https://pubs.rsc.org/en/content/articlelanding/2025/ob/d5ob00400d</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d5ob00400d" target="_blank" >10.1039/d5ob00400d</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Substituent effects of fluorinated bambusurils on their anion transport

Popis výsledku v původním jazyce

Anionophores are molecules that can transport ions across membranes. Several structural design criteria must be met for anionophores to be highly active. Fluorinated anionophores are usually more potent than their non-fluorinated analogues due to their higher lipophilicity and increased affinity for anions. Clear structure-activity relationships have been described for small and relatively simple anionophores. However, such studies are more challenging for large and macrocyclic anionophores, as their preparation is usually more complicated, limiting the number of compounds tested in anion transport studies. Here we present a series of twelve macrocyclic bambusuril anion transporters to investigate how variations in fluorinated substituents affect their transport properties. Measurements of Cl-/HCO3- antiport activities in liposomes revealed links between parameters such as lipophilicity or substituent polarity and transport activity. For some bambusurils, an unusually large effect of the presence of cholesterol in the membrane on transport activity was found. Further studies showed that for very potent anion receptors, such as the bambusurils described here, the binding selectivity towards anions becomes more important than the absolute binding affinity to anions when considering anion exchange across the membrane.

Název v anglickém jazyce

Substituent effects of fluorinated bambusurils on their anion transport

Popis výsledku anglicky

Anionophores are molecules that can transport ions across membranes. Several structural design criteria must be met for anionophores to be highly active. Fluorinated anionophores are usually more potent than their non-fluorinated analogues due to their higher lipophilicity and increased affinity for anions. Clear structure-activity relationships have been described for small and relatively simple anionophores. However, such studies are more challenging for large and macrocyclic anionophores, as their preparation is usually more complicated, limiting the number of compounds tested in anion transport studies. Here we present a series of twelve macrocyclic bambusuril anion transporters to investigate how variations in fluorinated substituents affect their transport properties. Measurements of Cl-/HCO3- antiport activities in liposomes revealed links between parameters such as lipophilicity or substituent polarity and transport activity. For some bambusurils, an unusually large effect of the presence of cholesterol in the membrane on transport activity was found. Further studies showed that for very potent anion receptors, such as the bambusurils described here, the binding selectivity towards anions becomes more important than the absolute binding affinity to anions when considering anion exchange across the membrane.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA23-05271S" target="_blank" >GA23-05271S: Chemická modifikace bambusurilů pro úpravu jejich vazebné afinity a selektivity</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2025

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Organic and Biomolecular Chemistry

ISSN

1477-0520

e-ISSN

1477-0539

Svazek periodika

23

Číslo periodika v rámci svazku

43

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

14

Strana od-do

9908-9921

Kód UT WoS článku

001467446100001

EID výsledku v databázi Scopus

2-s2.0-105002801027