Potential of graphene oxide as a drug delivery system for Sumatriptan: a detailed density functional theory study

References

• An, X., & Jimmy, C. Y. (2011). Graphene-based photocatalytic composites. RSC Advances, 1(8), 1426–1434. doi:10.1039/c1ra00382h
   Web of Science ®Google Scholar
• Boota, M., Chen, C., Bécuwe, M., Miao, L., & Gogotsi, Y. (2016). Pseudocapacitance and excellent cyclability of 2,5-dimethoxy-1,4-benzoquinone on graphene. Energy & Environmental Science, 9(8), 2586–2594. doi:10.1039/C6EE00793G
   Web of Science ®Google Scholar
• Boys, S. F., & Bernardi, F. (1970). The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors. Molecular Physics, 19(4), 553–566. doi:10.1080/00268977000101561
   Web of Science ®Google Scholar
• Chen, C., Boota, M., Xie, X., Zhao, M., Anasori, B., Ren, C. E., Miao, L., Jiang, J., & Gogotsi, Y. (2017). Charge transfer induced polymerization of edot confined between 2d titanium carbide layers. Journal of Materials Chemistry A, 5(11), 5260–5265. doi:10.1039/C7TA00149E
   Web of Science ®Google Scholar
• Cossi, M., Barone, V., Cammi, R., & Tomasi, J. (1996). Ab initio study of solvated molecules: A new implementation of the polarizable continuum model. Chemical Physics Letters, 255(4–6), 327–335. doi:10.1016/0009-2614(96)00349-1
   Web of Science ®Google Scholar
• Dastoorani, P., Khalilzadeh, M. A., Khaleghi, F., Maghsoodlou, M. T., Kaminsky, W., & Rad, A. S. (2019). Experimental and computational studies on the synthesis of diastereoselective natural-based meldrum spiro dibenzofuran derivatives. New Journal of Chemistry, 43(17), 6615–6621. doi:10.1039/C9NJ00766K
   Web of Science ®Google Scholar
• Ding, S., Chen, J. S., Luan, D., Boey, F. Y. C., Madhavi, S., & Lou, X. W. D. (2011). Graphene-supported anatase tio 2 nanosheets for fast lithium storage. Chemical Communications, 47(20), 5780–5782. doi:10.1039/c1cc10687b
   PubMed Web of Science ®Google Scholar
• Dreyer, D. R., Park, S., Bielawski, C. W., & Ruoff, R. S. (2010). The chemistry of graphene oxide. Chemical Society Reviews, 39(1), 228–240. doi:10.1039/b917103g
   PubMed Web of Science ®Google Scholar
• Frisch, M., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., … Fox, D. J. (2014). Gaussian 09, Revision D.01. Wallingford, CT: Gaussian, Inc.
   Google Scholar
• Ganji, M., Yazdani, H., & Mirnejad, A. (2010). B36n36 fullerene-like nanocages: A novel material for drug delivery. Physica E: Low-Dimensional Systems and Nanostructures, 42(9), 2184–2189. doi:10.1016/j.physe.2010.04.018
   Web of Science ®Google Scholar
• Ghosh, M., Brahmachari, S., & Das, P. K. (2014). Ph‐responsive single walled carbon nanotube dispersion for target specific release of doxorubicin to cancer cells. Macromolecular Bioscience, 14(12), 1795–1806. doi:10.1002/mabi.201400290
   PubMed Web of Science ®Google Scholar
• Goerigk, L. (2014). How do dft-dcp, dft-nl, and dft-d3 compare for the description of london-dispersion effects in conformers and general thermochemistry? Journal of Chemical Theory and Computation, 10(3), 968–980. doi:10.1021/ct500026v
   PubMed Web of Science ®Google Scholar
• Guldi, D. M., & Sgobba, V. (2011). Carbon nanostructures for solar energy conversion schemes. Chemical Communications, 47(2), 606–610. doi:10.1039/C0CC02411B
   PubMed Web of Science ®Google Scholar
• Hasanzade, Z., & Raissi, H. (2018). Density functional theory calculations and molecular dynamics simulations of the adsorption of ellipticine anticancer drug on graphene oxide surface in aqueous medium as well as under controlled pH conditions. Journal of Molecular Liquids, 255, 269–278. doi:10.1016/j.molliq.2018.01.159
   Web of Science ®Google Scholar
• Hasanzade, Z., & Raissi, H. (2019). Assessment of the chitosan-functionalized graphene oxide as a carrier for loading thioguanine, an antitumor drug and effect of urea on adsorption process: Combination of dft computational and molecular dynamics simulation studies. Journal of Biomolecular Structure and Dynamics, 37(10), 2487–2497. doi:10.1080/07391102.2018.1496140
   PubMed Web of Science ®Google Scholar
• Iijima, S. (1991). Helical microtubules of graphitic carbon. Nature, 354(6348), 56–58. doi:10.1038/354056a0
   Web of Science ®Google Scholar
• Iijima, S., & Ichihashi, T. (1993). Single-shell carbon nanotubes of 1-nm diameter. Nature, 363(6430), 603–605. doi:10.1038/363603a0
   Web of Science ®Google Scholar
• Khodashenas, B., Ardjmand, M., Sharifzadeh Baei, M., Shokuhi Rad, A., & Akbarzadeh, A. (2020). Conjugation of pectin biopolymer with Au‐nanoparticles as a drug delivery system: Experimental and DFT studies. Applied Organometallic Chemistry. doi:10.1002/aoc.5609
   Web of Science ®Google Scholar
• Koninti, R. K., Sengupta, A., Gavvala, K., Ballav, N., & Hazra, P. (2014). Loading of an anti-cancer drug onto graphene oxide and subsequent release to DNA/rna: a direct optical detection. Nanoscale, 6(5), 2937–2944. doi:10.1039/C3NR06081K
   PubMed Web of Science ®Google Scholar
• Li, T., Amari, T., Semba, K., Yamamoto, T., & Takeoka, S. (2017). Construction and evaluation of ph-sensitive immunoliposomes for enhanced delivery of anticancer drug to erbb2 over-expressing breast cancer cells. Nanomedicine: Nanotechnology, Biology and Medicine, 13(3), 1219–1227. doi:10.1016/j.nano.2016.11.018
   PubMed Web of Science ®Google Scholar
• Liang, L., Shen, J.-W., & Wang, Q. (2017). Molecular dynamics study on DNA nanotubes as drug delivery vehicle for anticancer drugs. Colloids and Surfaces B: Biointerfaces, 153, 168–173. doi:10.1016/j.colsurfb.2017.02.021
   PubMed Web of Science ®Google Scholar
• Liu, X., Wang, X., Li, J., & Wang, X. (2016). Ozonated graphene oxides as high efficient sorbents for sr (ii) and u (vi) removal from aqueous solutions. Science China Chemistry, 59(7), 869–877.
   Web of Science ®Google Scholar
• Liu, Z., Robinson, J. T., Sun, X., & Dai, H. (2008). Pegylated nanographene oxide for delivery of water-insoluble cancer drugs. Journal of the American Chemical Society, 130(33), 10876–10877. doi:10.1021/ja803688x
   PubMed Web of Science ®Google Scholar
• Lu, K.-Y., Li, R., Hsu, C.-H., Lin, C.-W., Chou, S.-C., Tsai, M.-L., & Mi, F.-L. (2017). Development of a new type of multifunctional fucoidan-based nanoparticles for anticancer drug delivery. Carbohydrate Polymers, 165, 410–420. doi:10.1016/j.carbpol.2017.02.065
   PubMed Web of Science ®Google Scholar
• Meng, S., Maragakis, P., Papaloukas, C., & Kaxiras, E. (2007). DNA nucleoside interaction and identification with carbon nanotubes. Nano Letters, 7(1), 45–50. doi:10.1021/nl0619103
   PubMed Web of Science ®Google Scholar
• Mirmotahari, M., Sani, E., Shokuhi Rad, A., & Khalilzadeh, M. A. (2019). Calcium-doped single-wall nanotubes (ca/swcnts) as a superior carrier for atropine drug delivery: A quantum-chemical study in gas and solvent phases. Journal of Biomolecular Structure and Dynamics, 37(16), 4267–4273. doi:10.1080/07391102.2018.1546233
   PubMed Web of Science ®Google Scholar
• Mohtat, B., Siadati, S. A., Khalilzadeh, M. A., & Zareyee, D. (2018). The concern of emergence of multi-station reaction pathways that might make stepwise the mechanism of the 1, 3-dipolar cycloadditions of azides and alkynes. Journal of Molecular Structure, 1155, 58–64. doi:10.1016/j.molstruc.2017.10.034
   Web of Science ®Google Scholar
• Mukhopadhyay, S., Scheicher, R. H., Pandey, R., & Karna, S. P. (2011). Sensitivity of boron nitride nanotubes toward biomolecules of different polarities. The Journal of Physical Chemistry Letters, 2(19), 2442–2447. doi:10.1021/jz2010557
   Web of Science ®Google Scholar
• Novoselov, K. S., Geim, A. K., Morozov, S. V., Jiang, D., Zhang, Y., Dubonos, S. V., Grigorieva, I. V., Firsov, A. A. (2004). Electric field effect in atomically thin carbon films. Science, 306(5696), 666–669. doi:10.1126/science.1102896
   PubMed Web of Science ®Google Scholar
• Orecchioni, M., Cabizza, R., Bianco, A., & Delogu, L. G. (2015). Graphene as cancer theranostic tool: Progress and future challenges. Theranostics, 5(7), 710–723. doi:10.7150/thno.11387
   PubMed Web of Science ®Google Scholar
• Pantarotto, D., Singh, R., McCarthy, D., Erhardt, M., Briand, J.-P., Prato, M., Kostarelos, K., & Bianco, A. (2004). Functionalized carbon nanotubes for plasmid DNA gene delivery. Angewandte Chemie International Edition, 43(39), 5242–5246. doi:10.1002/anie.200460437
   PubMed Web of Science ®Google Scholar
• Sanchez, C., Shea, K. J., & Kitagawa, S. (2011). Recent progress in hybrid materials science. Chemical Society Reviews, 40(2), 471–472. doi:10.1039/c1cs90001c
   PubMed Web of Science ®Google Scholar
• Shenderova, O., Zhirnov, V., & Brenner, D. (2002). Carbon nanostructures. Critical Reviews in Solid State and Materials Sciences, 27(3-4), 227–356. doi:10.1080/10408430208500497
   Web of Science ®Google Scholar
• Sheshala, R., Khan, N., & Darwis, Y. (2011). Formulation and optimization of orally disintegrating tablets of sumatriptan succinate. Chemical & Pharmaceutical Bulletin, 59(8), 920–928. doi:10.1248/cpb.59.920
   PubMed Web of Science ®Google Scholar
• Singla, P., Riyaz, M., Singhal, S., & Goel, N. (2016). Theoretical study of adsorption of amino acids on graphene and bn sheet in gas and aqueous phase with empirical dft dispersion correction. Physical Chemistry Chemical Physics, 18(7), 5597–5604. doi:10.1039/C5CP07078C
   PubMed Web of Science ®Google Scholar
• Siqueira, J. R., Jr., Caseli, L., Crespilho, F. N., Zucolotto, V., & Oliveira, O. N., Jr. (2010). Immobilization of biomolecules on nanostructured films for biosensing. Biosensors and Bioelectronics, 25(6), 1254–1263. doi:10.1016/j.bios.2009.09.043
   PubMed Web of Science ®Google Scholar
• Song, W., Yang, T., Wang, X., Sun, Y., Ai, Y., Sheng, G., Hayat, T., Wang, X. (2016). Experimental and theoretical evidence for competitive interactions of tetracycline and sulfamethazine with reduced graphene oxides. Environmental Science: Nano, 3(6), 1318–1326. doi:10.1039/C6EN00306K
   Web of Science ®Google Scholar
• Sun, X., Liu, Z., Welsher, K., Robinson, J. T., Goodwin, A., Zaric, S., & Dai, H. (2008). Nano-graphene oxide for cellular imaging and drug delivery. Nano Research, 1(3), 203–212. doi:10.1007/s12274-008-8021-8
   PubMed Web of Science ®Google Scholar
• Torchilin, V. P. (2005). Lipid-core micelles for targeted drug delivery. Current Drug Delivery, 2(4), 319–327. doi:10.2174/156720105774370221
   PubMedGoogle Scholar
• Vargas-Sánchez, R., Mendoza-Wilson, A., Balandrán-Quintana, R., Torrescano-Urrutia, G., & Sánchez-Escalante, A. (2015). Study of the molecular structure and chemical reactivity of pinocembrin by dft calculations. Computational and Theoretical Chemistry, 1058, 21–27. doi:10.1016/j.comptc.2015.01.014
   Web of Science ®Google Scholar
• Willner, I., & Willner, B. (2010). Biomolecule-based nanomaterials and nanostructures. Nano Letters, 10(10), 3805–3815. doi:10.1021/nl102083j
   PubMed Web of Science ®Google Scholar
• Yu, S., Wang, X., Yao, W., Wang, J., Ji, Y., Ai, Y., … Wang, X. (2017). Macroscopic, spectroscopic, and theoretical investigation for the interaction of phenol and naphthol on reduced graphene oxide. Environmental Science & Technology, 51(6), 3278–3286. doi:10.1021/acs.est.6b06259
   PubMed Web of Science ®Google Scholar
• Zardoost, M. R., Khalilzadeh, M. A., & Ataei, M. S. (2014). Effect of fluorine substitution on the reaction between methylene and acetone: a dft study. Progress in Reaction Kinetics and Mechanism, 39(1), 53–61. doi:10.3184/97809059274714X13874723178160
   Web of Science ®Google Scholar
• Zhang, L., Xia, J., Zhao, Q., Liu, L., & Zhang, Z. (2010). Functional graphene oxide as a nanocarrier for controlled loading and targeted delivery of mixed anticancer drugs. Small, 6(4), 537–544. doi:10.1002/smll.200901680
   PubMed Web of Science ®Google Scholar
• Zhu, S., Zhang, J., Qiao, C., Tang, S., Li, Y., Yuan, W., Li, B., Tian, L., Liu, F., Hu, R., Gao, H., Wei, H., Zhang, H., Sun, H., & Yang, B. (2011). Strongly green-photoluminescent graphene quantum dots for bioimaging applications. Chemical Communications, 47(24), 6858–6860. doi:10.1039/c1cc11122a
   PubMed Web of Science ®Google Scholar