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New representative of carbacylamidophosphates - diphenyl-N-(trichloroacetyl)-amidophosphate (HL), which contains two phenoxy substituents near the phosphoryl group, was synthesized, identified by elemental analysis and IR and NMR spectroscopy, and tested as a cytotoxic agent itself and in combination with C 60  fullerene.  According to molecular simulation results, C 60  fullerene and HL could interact with DNA and form a rigid complex stabilized by stacking interactions of HL phenyl groups with C 60  fullerene and DNA G nucleotide, as well as by interactions of HL CCl 3  group by ion-π bonds with C 60  molecule and by electrostatic bonds with DNA G nucleotide.  With the use of MTT test, the cytotoxic activity of HL against human leukemic CCRF-CM cells with IC 50  value detected at 10 μM concentration at 72 h of cells treatment was shown. Under combined action of 16 μM C 60  fullerene and HL, the value of IC 50  was detected at lower 5 μM HL concentration and at earlier 48 h period of incubation, besides the cytotoxic effect of HL was observed at a low 2.5 μM concentration at which HL by itself had no influence on cell viability. Binding of C 60  fullerene and HL with minor DNA groove with formation of a stable complex is assumed to be one of the possible reasons of their synergistic inhibition of CCRF-CЕM cells proliferation.  Application of C 60  fullerene in combination with 2.5 μM HL was shown to have no harmful effect on structural stability of blood erythrocytes membrane. Thus, combined action of C 60  fullerene and HL in a low concentration potentiated HL cytotoxic effect against human leukemic cells and was not followed by hemolytic effect.

nanoscale research letters

C60 Fullerene Effects on Diphenyl-N-(trichloroacetyl)-amidophosphate Interaction with DNA In Silico and Its Cytotoxic Activity Against Human Leukemic Cell Line In Vitro