Monensin A acid complexes as a model of electrogenic transport of sodium cation

Biochimica Et Biophysica Acta
Adam HuczynskiBogumil Brzezinski

Abstract

New Monensin A acid complexes with water molecule, sodium chloride and sodium perchlorate were obtained and studied by X-ray and (1)H, (13)C NMR and FT-IR methods as well as ab initio calculations. The crystal structure of the complexes indicates the complexation of the water molecule and Na(+) cation in the pseudo-cycle conformation of the Monensin acid molecule stabilised by intramolecular hydrogen bonds. Important for stabilisation of this structure is also the intermolecular hydrogen bonds with water molecule or the coordination bonds with Na(+) cation. It is demonstrated that the counterions forming intermolecular hydrogen bonds with OH groups influence the strength of the intramolecular hydrogen bonds, but they have no influence on the formation of pseudo-cyclic structure. Spectroscopic studies of the complexes in dichloromethane solution have shown that the pseudo-cyclic structure of the compounds is conserved. As follows from the ab initio calculations, the interactions between the Na(+) cation and the electronegative oxygen atoms of Monensin acid totally change the molecular electrostatic potential around the supramolecular Monensin acid-Na(+) cationic complex relative to that of the neutral Monensin acid molecule.

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Citations

Apr 16, 2013·BioMed Research International·Jacek Rutkowski, Bogumil Brzezinski
Mar 20, 2013·BioMed Research International·Daniel Aowicki, Adam Huczyński
Mar 8, 2014·European Journal of Medicinal Chemistry·Michał AntoszczakAdam Huczyński
Nov 28, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Michał AntoszczakAdam Huczyński
Jun 23, 2012·Bioorganic & Medicinal Chemistry Letters·Adam HuczyńskiBogumil Brzezinski
Sep 5, 2015·Bioorganic & Medicinal Chemistry Letters·Adam HuczyńskiJoanna Wietrzyk
Oct 1, 2015·Journal of Orthopaedic Research : Official Publication of the Orthopaedic Research Society·Anıl S ÇakmakMenemşe Gümüşderelioğlu
Oct 20, 2012·Bioorganic & Medicinal Chemistry Letters·Adam HuczyńskiBogumil Brzezinski
Oct 19, 2013·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·Bruno A RochaAnderson R M de Oliveira
Oct 16, 2012·Bioorganic & Medicinal Chemistry Letters·Adam Huczyński
Jun 22, 2016·ACS Medicinal Chemistry Letters·Björn BorgströmDaniel Strand
Sep 16, 2015·Antimicrobial Agents and Chemotherapy·Nicholas D PetersonAnthony D Baughn
Mar 7, 2020·Microbiology and Molecular Biology Reviews : MMBR·Elise A LamontAnthony D Baughn
Mar 23, 2020·Cancer Discovery·Koen M O GalenkampCosimo Commisso
Jan 6, 2019·European Journal of Medicinal Chemistry·Michał Antoszczak
May 7, 2021·Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan·Katsuharu Tsuchida

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