Synthesis, spectroscopy, theoretical and biological studies of new gramine-steroids salts and conjugates

Steroids
Weronika KozaneckaMateusz Gierszewski

Abstract

New gramine connections with bile acids (lithocholic, deoxycholic, cholic) and sterols (cholesterol, cholestanol) were synthesized. The structures of products were confirmed by spectral (NMR, FT-IR) analysis, mass spectrometry (ESI-MS) as well as PM5 semiempirical methods. Unexpectedly, the products of the reaction of gramine with cholesterol and cholestanol were symmetrical compounds consisting of two molecules of sterols connected by N(CH3)2 group. All new synthesized compounds interact in vitro with the human erythrocyte membrane and alter discoid erythrocyte shape inducing stomatocytosis or echinocytosis. Increase in the incorporation of the fluorescent dye merocyanine 540 (MC540) into the erythrocyte membrane indicates that new compounds at sublytic concentrations are capable of disturbing membrane phospholipids asymmetry and loosening the molecular packing of phospholipids in the bilayer. Gramine significantly decreases the membrane partitioning properties as well as haemolytic activity of lithocholic acid in its new salt. Moreover, both deoxycholic and cholic acids completely lost their membrane perturbing activities in the gramine salts. On the other hand, the capacity of new gramine-sterols connections to alter the ery...Continue Reading

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Citations

Dec 15, 2015·Chemico-biological Interactions·Karolina Malczewska-JaskółaLucyna Mrówczyńska
Apr 20, 2018·Free Radical Research·Beata JasiewiczLucyna Mrówczyńska
Jan 2, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Hélio M T AlbuquerqueArtur M S Silva
Jul 31, 2021·Scientific Reports·Beata JasiewiczLucyna Mrówczyńska

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