Toward Engineering Intra-Receptor Interactions into Bis(crown ethers)

Autor:	Martin R. Krause, Stefan Kubik
Rok vydání:	2012
Předmět:	Pharmacology chemistry.chemical_classification Chemistry Diastereomer Cooperative binding Isothermal titration calorimetry Plant Science General Medicine Alkali metal Medicinal chemistry Ion Hydrophobic effect Solvent Complementary and alternative medicine Drug Discovery Crown ether
Zdroj:	Natural Product Communications. 7:1934578X1200700
ISSN:	1555-9475 1934-578X
DOI:	10.1177/1934578x1200700314
Popis:	A synthetic receptor was designed in which cooperative binding of two crown ether moieties to an alkali metal ion simultaneously causes two hydrophobic substituents not involved in direct host-guest interactions to converge. Hydrophobic interactions between these substituents can be expected to contribute to the overall complex stability. Independent binding studies involving two diastereoisomers of this bis(crown ether), one in which intra-receptor interactions between the substituents are potentially possible and one in which they are not, using isothermal titration calorimetry showed that both isomers bind potassium ions in different solvent mixtures with the same overall affinity. Profound differences were observed for each isomer, however, in the enthalpies and entropies of binding, which are consistent with intra-receptor interactions in one compound. These interactions are counteracted by enthalpy-entropy compensation so that no overall improvement in cation affinity could be observed.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::0f6f7c444f1a35df770a1e0b46fd3816 https://doi.org/10.1177/1934578x1200700314 Zobrazit plný text záznamu