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

摘要: New gramine connections with bile acids (lithocholic, deoxycholic, cholic) and sterols (cholesterol, cholestanol) were synthesized. The structures of products confirmed by spectral (NMR, FT-IR) analysis, mass spectrometry (ESI-MS) as well PM5 semiempirical methods. Unexpectedly, the reaction cholesterol cholestanol symmetrical compounds consisting two molecules connected N(CH3)2 group. All new synthesized interact in vitro human erythrocyte membrane alter discoid shape inducing stomatocytosis or echinocytosis. Increase incorporation fluorescent dye merocyanine 540 (MC540) into indicates that at sublytic concentrations are capable disturbing phospholipids asymmetry loosening molecular packing bilayer. Gramine significantly decreases partitioning properties haemolytic activity lithocholic acid its salt. Moreover, both deoxycholic cholic completely lost their perturbing activities salts. On other hand, capacity gramine-sterols to structure permeability is much higher comparison alone. dual effect on cell observed our study should not be neglected vivo.