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Theoretical study on carbonaceous materials as high efficient carriers for crizotinib drug in liquid water by density functional theory approach

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Abstract

In order to get a precise insight into the nature of the intermolecular interaction of crizotinib drug with carbon nanomaterials, i.e., fullerene C70 and graphene nanosheet as high efficient carriers, the density functional theory calculations are applied on the binding strength, the molecular structures, electronic properties, and charge transfer in the water phase. Based on the calculated adsorption energy values, the physical nature for the interaction of the adsorbed drug with carbon nanostructures is approved. The obtained results suggest that crizotinib drug exhibits the strongest affinity for the adsorption on graphene nanosheet in comparison to fullerene C70. By considering the optimized geometries of the considered complexes, the π–π stacking interactions between π orbitals of the carbon nanostructures and the six-membered aromatic ring of the adsorbed molecule are observed. As a result of the physisorption process, no structural or electronic change of the adsorbed drug is found. Analysis of the energetic parameter of atoms-in-molecule method suggests medium strength intermolecular interaction of crizotinib drug with carbon nanostructures with partially covalent nature. The interactions of crizotinib drug and carbon nanostructures on the basis of two reactivity descriptors such as the overall stabilization energy and the fractional number of electrons transferred have been explained. The theoretical results show that the interaction of graphene nanosheet with crizotinib agent is more favorable than fullerene C70. The analysis of the natural bond orbital shows the capability of the carbon nanostructures to accept precisely the electron from crizotinib drug molecule during the adsorption process.

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Abbreviations

C60:

Fullerene

DFT:

Density functional theory

GNS:

Graphene nanosheet

MD:

Molecular dynamics

DOX:

Doxorubicin

CPT:

Camptothecin

AIM:

Atoms-in-molecule

CTZ:

Crizotinib

SCRF:

Self-consistent reaction field

PCM:

Polarized continuum model

BSSE:

Basis set superposition error

Eads:

Adsorption energy

NBO:

Natural bond orbital analysis

HOMO:

Highest occupied molecular orbital

LUMO:

Lowest unoccupied molecular orbital

MEP:

Molecular electrostatic potential

HOMA:

Harmonic oscillator model of aromaticity

BCP:

Bond critical point

NCI:

Non-covalent interaction

RDG:

Reduced density gradient

TDOS:

Total density of states

PDOS:

Projected density of state

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Authors and Affiliations

  1. Chemistry Department, Payame Noor University, P.O. Box 19395-3697, Tehran, Iran

    Mohammad Kia Kiani, Ashraf Sadat Ghasemi & Fatemeh Ravari

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  1. Mohammad Kia Kiani
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  2. Ashraf Sadat Ghasemi
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  3. Fatemeh Ravari
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Kiani, M.K., Ghasemi, A.S. & Ravari, F. Theoretical study on carbonaceous materials as high efficient carriers for crizotinib drug in liquid water by density functional theory approach. Struct Chem 31, 1553–1561 (2020). https://doi.org/10.1007/s11224-020-01522-y

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