282
Views
58
CrossRef citations to date
0
Altmetric
Research Article

Screening of the structural, topological, and electronic properties of the functionalized Graphene nanosheets as potential Tegafur anticancer drug carriers using DFT method

&
Pages 2517-2529 | Received 23 May 2017, Accepted 18 Jul 2017, Published online: 22 Aug 2017

References

  • Ali-Boucetta, H., Hanene, B. D., Raveendran-Nair, R., Servant, A., Van den Bossche, J., & Kostarelos, K. (2013). Purified graphene oxide dispersions lack in vitro cytotoxicity and in vivo pathogenicity. Advanced Healthcare Materials, 2, 433–441. doi:10.1002/adhm.201200248
  • Anota, E. C., Escobedo-Morales, A., Villanueva, M. S., Vázquez-Cuchillo, O., & Rosas, E. R. (2013). On the influence of point defects on the structural and electronic properties of graphene-like sheets: A molecular simulation study. Journal of Molecular Modeling, 19, 839–846. doi:10.1007/s00894-012-1612-z
  • Arias, J. L., López-Viota, M., Gallardo, V., & Ruiz, M. A. (2010). Chitosan nanoparticles as a new delivery system for the chemotherapy agent tegafur. Drug Development and Industrial Pharmacy, 36, 744–750. doi:10.3109/03639040903517914
  • Attaran Toosy, N. K., Raissi, H., & Zaboli, M. (2016). Theoretical calculations of intramolecular hydrogen bond of the 2-Amino-2, 4, 6-cycloheptatrien-1-one in the gas phase and solution: Substituent effects and their positions. Journal of Theoretical and Computational Chemistry, 15, 1650063. doi:10.1142/S0219633616500632
  • Bader, R. F. W. (1990). Atoms in molecules: A quantum theory. New York, NY: Oxford University Press.
  • Baniasadi, H., Ramazani, S. A., Mashayekhan, S., & Ghaderinezhad, F. (2014). Preparation of conductive polyaniline/graphene nanocomposites via in situ emulsion polymerization and product characterization. Synthetic Metals, 196, 199–205. doi:10.1016/j.synthmet.2014.08.007
  • Biegler-König, F., Schönbohm, J., & Bayles, D. (2001). AIM2000–A program to analyze and visualize atoms in molecules. Journal of Computational Chemistry, 22, 545–559. doi:10.1002/1096-987X(20010415)22:5<545::AID-JCC1027>3.0.CO;2-Y
  • Boys, F. S., & Bernardi, F. (1970). The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors. Molecular Physics, 19, 553–566. doi:10.1080/00268977000101561
  • Brown, D. M., Kinloch, I. A., Bangert, U., Windle, A. H., Walter, D. M., Walker, G. S., & Stone, V. I. C. K. I. (2007). An in vitro study of the potential of carbon nanotubes and nanofibres to induce inflammatory mediators and frustrated phagocytosis. Carbon, 45, 1743–1756. doi:10.1016/j.carbon.2007.05.011
  • Chai, J.-D., & Head-Gordon, M. (2008a). Systematic optimization of long-range corrected hybrid density functionals. The Journal of Chemical Physics, 128, 084106. doi:10.1063/1.2834918
  • Chai, J.-D., & Head-Gordon, M. (2008b). Long-range corrected hybrid density functionals with damped atom–atom dispersion corrections. Physical Chemistry Chemical Physics, 10, 6615–6620. doi:10.1039/B810189B
  • Chu, M., Dong, C., Zhu, H., Cai, X., Dong, H., Ren, T., … Li, Y. (2013). Biocompatible polyethylenimine-graft-dextran catiomer for highly efficient gene delivery assisted by a nuclear targeting ligand. Polymer Chemistry, 4, 2528–2539. doi:10.1039/C3PY21092H
  • Cooke, J. W. B., Bright, R., Coleman, M. J., & Jenkins, K. P. (2001). Process research and development of a dihydropyrimidine dehydrogenase inactivator: Large-scale preparation of eniluracil using a sonogashira coupling. Organic Process Research & Development, 5, 383–386. doi:10.1021/op0100100
  • Esfandfar, P., Falahati, M., & Saboury, A. (2016). Spectroscopic studies of interaction between CuO nanoparticles and bovine serum albumin. Journal of Biomolecular Structure and Dynamics, 34, 1962–1968. doi:10.1080/07391102.2015.1096213
  • Espinosa, E., & Molins, E. (2000). Retrieving interaction potentials from the topology of the electron density distribution: The case of hydrogen bonds. The Journal of Chemical Physics, 113, 5686–5694. doi:10.1063/1.1290612
  • Espionsa, E., Souhassou, M., Lachekar, H., & Lecomte, C. (1999). Topological analysis of the electron density in hydrogen bonds. Acta Crystallographica Section B: Structural Science, 55, 563–572. doi:10.1107/S0108768199002128
  • Esrafili, M. (2012). Investigation of H-bonding and halogen-bonding effects in dichloroacetic acid: DFT calculations of NQR parameters and QTAIM analysis. Journal of Molecular Modeling, 18, 5005–5016. doi:10.1007/s00894-012-1496-y
  • Fleming, I. (2010). Molecular orbitals and organic chemical reactions, reference edition. New York, NY: Department of Chemistry, University of Cambridge, Wiley.10.1002/9780470689493
  • Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., & Millam, J. M. (2003). Gaussian 03, revision C.02 (or D.01). Pittsburgh, PA: Gaussian Inc.
  • Ghiassi, H., & Raissi, H. (2015). Investigation of adsorption properties of CS2 on interior and exterior surfaces of single-walled silicon-carbide nanotubes and effect of applied electric field: Electronic structure, charge density and NMR studies. RSC Advances, 5, 84022–84037. doi:10.1039/c5ra06459 g
  • Ghiassi, H., & Raissi H. (2017). Doped-SiCNT as a promising sensor for detection of CS2 molecule. Journal of Sulfur Chemistry, 38, 372–383. doi: 10.1080/17415993.2017.1302449
  • Hajsalimi G., Taheri S., Shahi F., Pishkar L., Attar F., Ahmadi H., & Falahati M. (2017). Interaction of iron nanoparticles with nervous system: An invitro study. Journal of Biomolecular Structure and Dynamics, 1–10. doi: 10.1080/07391102.2017.1302819
  • Hillaireau, H., & Couvreur, P. (2009). Nanocarriers’ entry into the cell: Relevance to drug delivery. Cellular and Molecular Life Sciences, 66, 2873–2896. doi:10.1007/s00018-009-0053-z
  • Hoff, P. M., Lassere, Y., & Pazdur, R. (1999). Tegafur/uracil + calcium folinate in colorectal cancer. Drugs, 58, 77–83. doi:10.2165/00003495-199958003-00011
  • Hokmabady, L., Raissi, H., & Khanmohammadi, A. (2016). Interactions of the 5-fluorouracil anticancer drug with DNA pyrimidine bases: A detailed computational approach. Structural Chemistry, 27, 487–504. doi:10.1007/s11224-015-0578-8
  • Iikura, H., Tsuneda, T., Yanai, T., & Hirao, K. (2001). A long-range correction scheme for generalized-gradient-approximation exchange functionals. The Journal of Chemical Physics, 115, 3540–3544. doi:10.1063/1.1383587
  • Ikeda, K., Yoshisue, K., Matsushima, E., Nagayama, S., Kobayashi, K., Tyson, C. A., … Kawaguchi, Y. (2000). Bioactivation of Tegafur to 5-fluorouracil Is catalyzed by cytochrome P-450 2A6 in human liver microsomes in vitro 1. Clinical Cancer Research, 6, 4409–4415.
  • Jafari Azad, V., Kasravi, S., Alizadeh Zeinabad, H., Memar Bashi Aval, M., Saboury, A. A., Rahimi, A, & Falahati, M. (2016). Probing the conformational changes and peroxidase-like activity of cytochrome c upon interaction with iron nanoparticles. Journal of Biomolecular Structure and Dynamics,1–13. doi: 10.1080/07391102.2016.1222972
  • Kumar, P. V., Bardhan, N. M., Tongay, S., Wu, J., Belcher, A. M., & Grossman, J. C. (2014). Scalable enhancement of graphene oxide properties by thermally driven phase transformation. Nature chemistry, 6, 151–158. doi:10.1038/nchem.1820
  • Madaan, K., Kumar, S., Poonia, N., Lather, V., & Pandita, D. (2014). Dendrimers in drug delivery and targeting: Drug-dendrimer interactions and toxicity issues. Journal of Pharmacy And Bioallied Sciences, 6, 139–150. doi:10.4103/0975-7406.130965
  • Mahdavifar, Z., & Moridzadeh, R. (2014). Theoretical prediction of encapsulation and adsorption of platinum-anticancer drugs into single walled boron nitride and carbon nanotubes. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 79, 443–457. doi:10.1007/s10847-013-0367-1
  • Mariam, J., Sivakami, S., & Dongre, P. M. (2017). Elucidation of structural and functional properties of albumin bound to gold nanoparticles. Journal of Biomolecular Structure and Dynamics, 35, 368–379. doi:10.1080/07391102.2016.1144223
  • Mastrobattista, E., Van Der Aa, M., Hennink, W. E., & Crommelin, D. J. A. (2006). Artificial viruses: A nanotechnological approach to gene delivery. Nature Reviews Drug Discovery, 5, 115–121. doi:10.1038/nrd1960
  • Mennucci, B. (2012). Polarizable continuum model. Wiley interdisciplinary reviews: Computational molecular science, 2, 386–404. doi:10.1002/wcms.1086
  • Miertus, S., Scrocco, E., & Tomasi, J. (1981). Electrostatic interaction of asolute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects. Chemical Physics, 55, 117–129. doi:10.1016/0301-0104(81)85090-2
  • Parr, R. G., & Pearson, R. G. (1983). Absolute hardness: Companion parameter to absolute electronegativity. Journal of the American Chemical Society, 105, 7512–7516. doi:10.1021/ja00364a005
  • Parr, R. G., Szentpaly, L. V., & Liu, S. (1999). Electrophilicity index. Journal of the American Chemical Society, 121, 1922–1924. doi:10.1021/ja983494x
  • Pasban, S., Raissi, H., & Mollania, F. (2016). Solvent effects on the structural, electronic properties and intramolecular N–H O hydrogen bond strength of 5-aminomethylene-pyrimidine-2,4,6 trion with DFT calculations. Journal of Molecular Liquids, 215, 77–87. doi:10.1016/j.molliq.2015.11.038
  • Prasad, O., Sinha, L., & Kumar, N. (2010). Theoretical Raman and IR spectra of tegafur and comparison of molecular electrostatic potential surfaces, polarizability and hyerpolarizability of tegafur with 5-fluoro-uracil by density functional theory. Journal of Atomic and Molecular Sciences, 1, 201–214. doi:10.4208/jams.032510.042010a
  • Pulskamp, K., Woerle-Knirsch, J. M., Hennrich, F., Kern, K., & Krug, H. F. (2007). Human lung epithelial cells show biphasic oxidative burst after single-walled carbon nanotube contact. Carbon, 45, 2241–2249. doi:10.1016/j.carbon.2007.06.054
  • Raissi, H., & Mollania, F. (2014). Immunosuppressive agent leflunomide: A SWNTs-immobilized dihydroortate dehydrogenase inhibitory effect and computational study of its adsorption properties on zigzag single walled (6,0) carbon and boron nitride nanotubes as controlled drug delivery devices. European Journal of Pharmaceutical Sciences, 56, 37–54. doi:10.1016/j.ejps.2014.02.006
  • Ren, T. B., Li, L., Cai, X. J., Dong, H. Q., Liu, S. M., & Li, Y. Y. (2012). Engineered polyethylenimine/graphene oxide nanocomposite for nuclear localized gene delivery. Polymer Chemistry, 3, 2561–2569. doi:10.1039/C2PY20343J
  • Rosas, J. H., Gutiérrez, R. R., Escobedo-Morales, A., & Anota, E. C. (2011). First principles calculations of the electronic and chemical properties of graphene, graphane, and graphene oxide. Journal of Molecular Modeling, 17, 1133–1139. doi:10.1007/s00894-010-0818-1
  • Safdari, F., Raissi, H., Shahabi, M., & Zaboli, M. (2017). DFT calculations and molecular dynamics simulation study on the adsorption of 5-fluorouracil anticancer drug on Graphene oxide nanosheet as a drug delivery vehicle. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 27, 805–817. doi:10.1007/s10904-017-0525-9
  • Savin, A., & Flad, H.-J. (1995). Density functionals for the Yukawa electron-electron interaction. International Journal of Quantum Chemistry, 56, 327–332. doi:10.1002/qua.560560417
  • Shahabi, M., & Raissi, H. (2016a). Investigation of the molecular structure, electronic properties, AIM, NBO, NMR and NQR parameters for the interaction of Sc, Ga and Mg-doped (6,0) aluminum nitride nanotubes with COCl2 gas by DFT study. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 84, 99–114. doi:10.1007/s10847-015-0587-7
  • Shahabi, M., & Raissi, H. (2016b). Molecular dynamics simulation and quantum chemical studies on the investigation of aluminum nitride nanotube as phosgene gas sensor. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 86, 305–322. doi:10.1007/s10847-016-0664-6
  • Shahabi, M., & Raissi H. (2017). Investigation of the solvent effect, molecular structure, electronic properties and adsorption mechanism of Tegafur anticancer drug on Graphene nanosheet surface as drug delivery system by molecular dynamics simulation and density functional approach. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 88, 159–169. doi: 10.1007/s10847-017-0713-9
  • Shahabi, M., Raissi, H., & Mollania, F. (2014). Electronic structures, intramolecular hydrogen bond interaction, and aromaticity of substituted 4-amino-3-penten-2-one in ground and electronic excited state. Structural Chemistry, 26, 491–506. doi: 10.1007/s11224-014-0505-4
  • Skariyachan, S., Parveen, A., & Garka, S. (2016). Nanoparticle Fullerene (C60) demonstrated stable binding with antibacterial potential towards probable targets of drug resistant Salmonella typhi–a computational perspective and in vitro investigation. Journal of Biomolecular Structure and Dynamics, 1–20, doi:10.1080/07391102.2016.1257441
  • Yang, X., Niu, G., Cao, X., Wen, Y., Xiang, R., Duan, H., & Chen, Y. (2012). The preparation of functionalized graphene oxide for targeted intracellular delivery of siRNA. Journal of Materials Chemistry, 22, 6649–6654. doi:10.1039/c2jm14718a
  • Zaboli, M., & Raissi, H. (2015). The analysis of electronic structures, adsorption properties, NBO, QTAIM and NMR parameters of the adsorbed hydrogen sulfide on various sites of the outer surface of aluminum phosphide nanotube: A DFT study. Structural Chemistry, 26, 1059–1075. doi:10.1007/s11224-015-0563-2
  • Zhang, N., Yin, Y., Xu, S. J., & Chen, W. S. (2008). 5-Fluorouracil: Mechanisms of resistance and reversal strategies. Molecules, 13, 1551–1569. doi:10.3390/molecules13081551
  • Zhang, L., Lu, Z., Zhao, Q., Huang, J., Shen, H., & Zhang, Z. (2011). Enhanced chemotherapy efficacy by sequential delivery of siRNA and anticancer drugs using PEI-grafted graphene oxide. Small, 7, 460–464. doi:10.1002/smll.201001522
  • Zhao, X., & Liu, P. (2014). Biocompatible graphene oxide as a folate receptor-targeting drug delivery system for the controlled release of anti-cancer drugs. RSC Advances., 4, 24232–24239. doi:10.1039/C4RA02466D

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.