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


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Article Info

DATE

2018-03-09

AUTHORS

A. Grebinyk, S. Prylutska, I. Grynyuk, B. Kolp, V. Hurmach, T. Sliva, V. Amirkhanov, V. Trush, O. Matyshevska, M. Slobodyanik, Yu. Prylutskyy, M. Frohme, U. Ritter

ABSTRACT

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 C60 fullerene.According to molecular simulation results, C60 fullerene and HL could interact with DNA and form a rigid complex stabilized by stacking interactions of HL phenyl groups with C60 fullerene and DNA G nucleotide, as well as by interactions of HL CCl3 group by ion-π bonds with C60 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 IC50 value detected at 10 μM concentration at 72 h of cells treatment was shown. Under combined action of 16 μM C60 fullerene and HL, the value of IC50 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 C60 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 C60 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 C60 fullerene and HL in a low concentration potentiated HL cytotoxic effect against human leukemic cells and was not followed by hemolytic effect. More... »

PAGES

81

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1186/s11671-018-2490-9

DOI

http://dx.doi.org/10.1186/s11671-018-2490-9

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https://app.dimensions.ai/details/publication/pub.1101393547

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/29524037


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20 schema:description 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 C60 fullerene.According to molecular simulation results, C60 fullerene and HL could interact with DNA and form a rigid complex stabilized by stacking interactions of HL phenyl groups with C60 fullerene and DNA G nucleotide, as well as by interactions of HL CCl3 group by ion-π bonds with C60 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 IC50 value detected at 10 μM concentration at 72 h of cells treatment was shown. Under combined action of 16 μM C60 fullerene and HL, the value of IC50 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 C60 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 C60 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 C60 fullerene and HL in a low concentration potentiated HL cytotoxic effect against human leukemic cells and was not followed by hemolytic effect.
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26 schema:keywords C60 fullerene
27 C60 molecules
28 CCRF
29 CCl3 group
30 DNA
31 DNA G
32 DNA groove
33 HL
34 HL concentrations
35 IC50
36 IC50 values
37 IR
38 MTT test
39 NMR spectroscopy
40 action
41 activity
42 agents
43 analysis
44 applications
45 blood
46 bonds
47 cell lines
48 cell proliferation
49 cell treatment
50 cell viability
51 cells
52 combination
53 combined action
54 complexes
55 concentration
56 cytotoxic activity
57 cytotoxic agents
58 cytotoxic effects
59 diphenyl
60 effect
61 electrostatic bonds
62 elemental analysis
63 formation
64 fullerenes
65 groove
66 group
67 h period
68 harmful effects
69 hemolytic effect
70 human leukemic cell lines
71 human leukemic cells
72 incubation
73 influence
74 inhibition
75 interaction
76 leukemic cell lines
77 leukemic cells
78 lines
79 low concentrations
80 membrane
81 minor DNA groove
82 molecular simulation results
83 molecules
84 new representative
85 period
86 phenoxy substituents
87 phenyl group
88 phosphoryl group
89 possible reasons
90 proliferation
91 reasons
92 representatives
93 results
94 rigid complexes
95 silico
96 simulation results
97 spectroscopy
98 stability
99 stable complexes
100 structural stability
101 substituents
102 synergistic inhibition
103 test
104 treatment
105 use
106 values
107 values of IC50
108 viability
109 vitro
110 schema:name C60 Fullerene Effects on Diphenyl-N-(trichloroacetyl)-amidophosphate Interaction with DNA In Silico and Its Cytotoxic Activity Against Human Leukemic Cell Line In Vitro
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