Synteza, struktura oraz aktywność biologiczna amidów Monenzyny A oraz ich kompleksów z kationami metali
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2011-05-17T10:57:18Z
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Synthesis, structure and biological activity of Monensin A amides and their complexes with metal cations
Abstract
Niniejsza praca przedstawia syntezę czterech nowych amidów monenzyny A – znanego antybiotyku jonoforowego. Przy pomocy metod spektroskopowych 1H, 13C NMR i FT-IR, spektrometrycznych ESI MS oraz obliczeń semiempirycznych PM5 określono struktury otrzymanych amidów monenzyny oraz ich kompleksów z kationami litu, sodu i potasu. Spektrometria masowa ESI MS posłużyła do określenia stechiometrii tworzonych kompleksów z kationami Li+, Na+ i K+, oraz preferencji kompleksowania tych kationów przez badane amidy. Otrzymano dwa kompleksy amidu fenylowego monenzyny z NaClO4 i amidu allilowego z Sr(ClO4)2 w postaci krystalicznej, których struktury określono metodami krystalograficznymi. Wykazano również przy zastosowaniu metody ESI MS zdolność kompleksowania kationów metali dwuwartościowych takich jak: Mg2+, Ca2+, Sr2+ i Ba2+ przez dwa amidy monenzyny, oraz określono najwyższe powinowactwo tych amidów do kationów Ca2+. Po raz pierwszy dostarczono eksperymentalnego dowodu na kompleksowanie kationu Sr2+ w hydrofilowej wnęce amidu monenzyny. Wszystkie cztery amidy zostały poddane badaniom aktywności przeciwdrobnoustrojowej względem bakterii Gram-dodatnich i wykazały relatywnie wysoką aktywność.
The paper reports the synthesis of four new amides of monensin A – a well known ionophoric antibiotic. The structures of the amides and their complexes with lithium, sodium and potassium cations were studied by 1H, 13C NMR, FT-IR spectroscopic methods, ESI MS spectrometric methods as well as PM5 semiempirical calculations. The ESI MS analysis was used to determine stoichiometry of the complexes with Li+, Na+ and K+, as well as complexation preferences of these cations. Two crystal complexes of N-phenyl amide of monensin with NaClO4 and N-allylamide with Sr(ClO4)2 were obtained and studied by X-ray method. The ability of complex formation with divalent metal cations (Mg2+, Ca2+, Sr2+ and Ba2+) was demonstrated using the ESI MS method. These studies also showed the highest complexation preference of the calcium cation. For the first time experimental evidence for complexation of Sr2+ cation in the cavity of monensin amide was provided. The in-vitro biological tests of four monensin A amides show their good activity towards some strains of Gram-positive bacteria.
The paper reports the synthesis of four new amides of monensin A – a well known ionophoric antibiotic. The structures of the amides and their complexes with lithium, sodium and potassium cations were studied by 1H, 13C NMR, FT-IR spectroscopic methods, ESI MS spectrometric methods as well as PM5 semiempirical calculations. The ESI MS analysis was used to determine stoichiometry of the complexes with Li+, Na+ and K+, as well as complexation preferences of these cations. Two crystal complexes of N-phenyl amide of monensin with NaClO4 and N-allylamide with Sr(ClO4)2 were obtained and studied by X-ray method. The ability of complex formation with divalent metal cations (Mg2+, Ca2+, Sr2+ and Ba2+) was demonstrated using the ESI MS method. These studies also showed the highest complexation preference of the calcium cation. For the first time experimental evidence for complexation of Sr2+ cation in the cavity of monensin amide was provided. The in-vitro biological tests of four monensin A amides show their good activity towards some strains of Gram-positive bacteria.
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Wydział Chemii: Zakład Biochemii
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jonofory, Ionophores, amidy monenzyny A, monensin A amides, metody spektroskopowe, spectroscopic methods, spektrometria ESI MS, ESI mass spectrometry, aktywność biologiczna, biological activity