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Current Molecular Medicine

Editor-in-Chief

ISSN (Print): 1566-5240
ISSN (Online): 1875-5666

Research Article

Investigation of Adsorption Tyrphostin AG528 Anticancer Drug Upon the CNT(6,6-6) Nanotube: A DFT Study

Author(s): Masoome Sheikhi*, Siyamak Shahab*, Radwan Alnajjar, Mahin Ahmadianarog and Sadegh Kaviani

Volume 19, Issue 2, 2019

Page: [91 - 104] Pages: 14

DOI: 10.2174/1566524019666190226111823

Price: $65

Abstract

Objective: In the present study, the interaction between drug Tyrphostin AG528 and CNT(6,6-6) nanotube by Density Functional Theory (DFT) calculations in solvent water has been investigated for the first time.

Methods and Results: According to the calculations, intermolecular hydrogen bonds take place between an active position of the molecule Tyrphostin AG528 and hydrogen atoms of the nanotube which play an important role in the stability of complex CNT(6,6- 6)/Tyrphostin AG528. The non-bonded interaction effects of the molecule Tyrphostin AG528 with CNT(6,6-6) nanotube on the electronic properties, chemical shift tensors and natural charge have also been detected. The natural bond orbital (NBO) analysis suggested that the molecule Tyrphostin AG528 as an electron donor and the CNT(6,6-6) nanotube play the role of an electron acceptor at the complex CNT(6,6-6)/Tyrphostin AG528.

Conclusion: The electronic spectra of the Tyrphostin AG528 drug and complex CNT(6,6-6)/Tyrphostin AG528 in solvent water were calculated by Time-Dependent Density Functional Theory (TD-DFT) for the investigation of adsorption effect of the Tyrphostin AG528 drug over nanotube on maximum wavelength. Then, the possibility of the use of CNT(6,6-6) nanotube for Tyrphostin AG528 delivery to the diseased cells has been established.

Keywords: Tyrphostin AG528, CNT(6, 6-6) nanotube, DFT, adsorption, NBO, anticancer.

[1]
Liu Z, Tabakman S, Welsher K, Dai H. Carbon nanotubes in biology and medicine: In vitro and in vivo detection, imaging and drug delivery. Nano Res 2009; 2: 85-120.
[2]
Peretz S, Regev O. Carbon nanotubes as nanocarriers in medicine. Curr Opin Colloid Interface Sci 2012; 17: 360-8.
[3]
Vashist SK, Zheng D, Pastorin G, Al-Rubeaan K, Luong JHT, Sheu F. Delivery of drugs and biomolecules using carbon nanotubes. Carbon 2011; 49: 4077-97.
[4]
Ji S, Liu C, Zhang B, et al. Carbon nanotubes in cancer diagnosis and therapy. Biochim.Biophys Acta (BBA)-. Rev Can 2010; 1806: 29-35.
[5]
Digge MS, Moon RS, Gattani SG. Applications of carbon nanotubes in drug delivery: A review. Int J Pharm Tech Res 2012; 4: 839-47.
[6]
Chandrasekhar P. CNT Applications in Drug and Biomolecule Delivery.In:Conducting Polymers, Fundamentals and Applications. Cham: Springer 2018; pp. 61-4.
[7]
Sharma S, Mehra NK, Jain K, Jain NK. Effect of functionalization on drug delivery potential of carbon nanotubes. Artif Cells Nanomed Biotechnol 2016; 44: 1851-60.
[8]
Mishra AK. Nanomedicine for drug delivery and therapeutics. John Wiley & Sons 2013.
[9]
Wilczewska AZ, Niemirowicz K, Markiewicz KH. Nanoparticles as drug delivery systems. Pharmacol Rep 2012; 64: 1020-37.
[10]
Lacerda L, Bianco A, Prato M, Kostarelos K. Carbon nanotubes as nanomedicines: From toxicology to pharmacology. Adv Drug Deliv Rev 2006; 58: 1460-70.
[11]
Parhi P, Mohanty C, Sahoo SK. Nanotechnology-based combinational drug delivery: An emerging approach for cancer therapy. Drug Discov Today 2012; 17: 1044-52.
[12]
Tripisciano C, Kraemer K, Taylor A, Borowiak-Palen E. Single-wall carbon nanotubes based anticancer drug delivery system. Chem Phys Lett 2009; 478: 200-5.
[13]
Panchapakesan B, Lu S, Sivakumar K, Taker K, Cesarone G, Wickstrom E. Single-wall carbon nanotube nanobomb agents for killing breast cancer cells. Nanobiotechnol 2005; 1: 133-9.
[14]
Meng L, Zhang X, Lu Q, Fei Z, Dyson PJ. Single walled carbon nanotubes as drug delivery vehicles: targeting doxorubicin to tumors. Biomater 2012; 33: 1689-98.
[15]
Zhang W, Zhang Z, Zhang Y. The application of carbon nanotubes in target drug delivery systems for cancer therapies. Nanoscale Res Lett 2011; 6: 1-22.
[16]
Zhang J, Yang PL, Gray NS. Targeting cancer with small molecule kinase inhibitors. Nat Rev Cancer 2009; 9: 28-39.
[17]
Levitzki A, Gazit A. Tyrosine kinase inhibition: an approach to drug development. Science 1995; 267: 1782-8.
[18]
Gschwind AM, Fischer O, Ullrich A. The discovery of receptor tyrosine kinases: Targets for cancer therapy. Nat Rev Cancer 2004; 4: 361-70.
[19]
Levitzki A, Mishani E. Tyrphostins and other tyrosine kinase inhibitors. Annu Rev Biochem 2006; 75: 93-109.
[20]
Levitzki A, Gazit A, Osherov N, Posner I, Gilon C. Inhibition of protein-tyrosine kinases by tyrphostins. Methods Enzymol 1991; 201: 37-61.
[21]
Yamamoto E, Kitano Y, Hasumi K. Elucidation of crucial structures for a catechol-based inhibitor of plasma hyaluronan-binding protein (factor VII activating protease) autoactivation. Biosci Biotechnol Biochem 2011; 75: 2070-2.
[22]
Fishbein I, Chorny M, Rabinovich L, Banai S, Gati I, Golomb G. Nanoparticulate delivery system of a tyrphostin for the treatment of restenosis. J Control Release 2000; 65: 221-9.
[23]
Fishbein I, Chorny M, Banai S, et al. Formulation and delivery mode affect disposition and activity of tyrphostin-loaded nanoparticles in the rat carotid model. Arterioscler Thromb Vasc Biol 2001; 21: 1434-9.
[24]
Xu H, Li L, Fan G, Chu X. DFT study of nanotubes as the drug delivery vehicles of Efavirenz. Comput Theor Chem 2018; 1131: 57-68.
[25]
El Khalifi M, Duverger E, Boulahdour H, Picaud F. Theoretical study of the interaction between carbon nanotubes and carboplatin anticancer molecules. Anal Methods 2015; 7: 10145-50.
[26]
Wang Y, Xu Z. Interaction mechanism of doxorubicin and SWCNT: protonation and diameter effects on drug loading and releasing. RSC Advances 2016; 6: 314-22.
[27]
Sheikhi M, Shahab S, Khaleghian M, Kumar R. Interaction between new anti-cancer drug syndros and CNT(6,6-6) nanotube for medical applications: Geometry optimization, molecular structure, spectroscopic (NMR, UV/Vis, excited state), FMO, MEP and HOMO-LUMO investigation. Appl Surf Sci 2018; 434: 504-13.
[28]
Sheikhi M, Shahab S, Khaleghian M, Hajikolaee FH, Balakhanava I, Alnajjar R. Adsorption properties of the molecule resveratrol on CNT (8, 0-10) nanotube: Geometry optimization, molecular structure, spectroscopic (NMR, UV/Vis, Excited State), FMO, MEP and HOMO-LUMO investigations. J Mol Struct 2018; 1160: 479-8.
[29]
Khattab M, Wang F, A. H.A. Clayton Conformational plasticity in tyrosine kinase inhibitor-kinase interactions revealed with fluorescence spectroscopy and theoretical calculations. J Phys Chem B 2018; 122: 4667-79.
[30]
Shahab S, Filippovich L, Sheikhi M, et al. Polarization, excited states, trans-cis properties and anisotropy of thermal and electrical conductivity of the 4-(phenyldiazenyl)aniline in PVA matrix. J Mol Struct 2017; 1141: 703-9.
[31]
Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian 09 revision A02. Gaussian, Inc., Wallingford CT. 2009.
[32]
Frisch A, Nielson AB, Holder AJ. GAUSSVIEW User Manual. Gaussian Inc., Pittsburgh, PA. 2000.
[33]
Sheikhi M, Shahab S, Filippovich L, Yahyaei H, Dikusar E, Khaleghian M. New derivatives of (E,E)-azomethines: Design, quantum chemical modeling, spectroscopic (FT-IR, UV/Vis, polarization) studies, synthesis and their applications: Experimental and theoretical investigations. J Mol Struct 2018; 1152: 368-85.
[34]
Shahab S, Sheikhi M, Filippovich L. DikusarAnatol’evich E, Yahyaei H. Quantum chemical modeling of new derivatives of (E,E)-azomethines: Synthesis, spectroscopic (FT-IR, UV/Vis, polarization) and thermophysical investigations. J Mol Struct 2017; 1137: 335-48.
[35]
Weinhold F, Landis CR. Natural Bond Orbitals and Extensions of Localized Bonding Concepts. Chem Educ Res Pract 2001; 2: 91-104.
[36]
Sheikhi M, Sheikh D. Quantum chemical investigations on phenyl-7,8- dihydro-[1,3]dioxolo[4,5-g] quinolin-6(5h)-one. Rev Roum Chim 2014; 59: 761-7.
[37]
Sheikhi M, Balali E, Lari H. Theoretical investigations on molecular structure, NBO, HOMO-LUMO and MEP analysis of two crystal structures of N-(2-benzoyl-phenyl) oxalyl: A DFT study. J Phys Theor Chem 2016; 13: 155-71.

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