Cycloaddition [2+2] interaction of some Corticosteroid drugs with C60 nano fullerene: A theoretical study

Document Type : Reasearch Paper


Department of Chemistry, Ayatollah Borujerdi University, Borujerd, Iran.


In this work, the quantum mechanics calculations were carried out to elucidate the adsorption behavior of some corticosteroid drugs (clobetasol, beclometasone, prednisolone, and methylprednisolone) on the surface of C60 nano-fullerene using density functional theory (DFT) at B3LYP/6-31G (d,p) level. After optimization of the structures, various parameters such as HOMO and LUMO energies, energy gap, adsorption energy, cohesive energy, chemical hardness, chemical potential, dipole moment, electrophilicity index and changes in the length of some bonds data were calculated. The results showed that the amounts of energy gap and chemical hardness are decreased with binding of corticosteroids to fullerene, while those of chemical potential and electrophilicity index are increased. It means that nanocarrier increases the drug reactivity. Also, binding and stabilization energies are increased. The C60-Clobetasol, C60-Beclometasone, C60-Prednisolone and C60-Methylprednisolone presented the adsorption energy with the values of 54.3478, -6.5263, 45.1586, and 947.8854 KJ in gas phase, respectively. Moreover, the solubility of nanocarrier has increased in the water solvent compared to the gas phase. These results can be considered in pharmacy for these types of drugs and similar systems. The presence of oxygen atoms in the structure of drugs increases the ability of nano-fullerene as a drug carrier, because the ability of nitrogen atoms to protonation in acidic environment weakens their binding to fullerene in the target cell.


[1] Heshmati P., Asadi Nouqabi A. A, (2009), Iranian Generic Drug Dictionary, Andisheh Rafi Publication.
[2] Teimouri F., Bahari Javan N., Rezaei Shirmard L., (2015), Generic drugs of Iran along with imported and prescription drugs with nursing care, ABADIS TEB Publishing, Tehran.
[3] Charman C., Williams H., (2003), The use of corticosteroids and corticosteroid phobia in atopic dermatitis. Clinics in Dermatol. 21: 193-200.
[4] Scrivens W. A., Tour J. M., Creek K. E., (1994), Synthesis of 14C-labeled C60, its suspension in water, and its uptake by human keratinocytes. J. Am. Chem. Soc., 116: 4517-4518.
[5] Fekri M. H., Omrani A., Jamehbozorgi S., Razavi Mehr M., (2019), Study of electrochemical and electronical properties on the some schiff base Ni complexes in DMSO solvent by computational methods. Adv. J. Chem. A. 2: 14-20.
[6] Naderi E., Mirzaei M., Saghaie L., Khodarahmi G. H., Gulseren O., (2017), Relaxations of methylpyridineone tautomers at the C60 surfaces: DFT studies, Int. J. Nano Dimens. 8: 124-131. 
[7] Faramarzi R., Falahati M., Mirzaei M., (2020), Interactions of fluorouracil by CNT and BNNT: DFT analyses. Adv. J. Sci. Eng. 1: 62-66.
[8] Zahra Javanshir Z., Razavi Mehr M., Fekri M. H., (2020), Experimental and computational studies on the electrochemical behavior of carvacrol and menthol. Iran. J. Chem. Chem. Eng. In Press.
[9] Ahmadi R., Jalali Sarvestani M. R., Sadeghi B., (2018), Computational study of the fullerene effects on the properties of 16 different drugs: A review. Int. J. Nano Dimens. 9: 325-335.
[10] Rezvan Baniasadi R., Harismah K., Sadeghi M., Mirzaei M., (2017), Adsorption of vitamin C on a fullerene surface: DFT Studies. J. Nanoanal. 4: 1-7.
[11] Mirali M., Jafariazar Z., Mirzaei M., (2021), Loading tacrine alzheimer's drug at the Carbon nanotube: DFT approach. Lab-in-Silico. 2: 3-8.
[12] Mirzaei M., (2013), Uracil-functionalized ultra-small (n, 0) boron nitride nanotubes (n= 3–6): Computational studies. Superlatt. Microstruc. 57: 44-50.
[13] Mirzaei M., (2020), Nanotechnology for science and engineering. Adv. J. Sci. Eng. 1: 67-68.
[14] More M. P., Deshmukh P. K., (2020), Computational studies and biosensory applications of graphene-based nanomaterials: A state-of-the-art review. Nanotechnol. 31: 432001.
[15] Zhao L., Li H., Tan L., (2017), A novel fullerene-based drug delivery system delivering doxorubicin for potential lung cancer therapy. J. Nanosci. Nanotechnol. 17: 5147-5154.
[16] Kamel M., Raissi H., Morsali A., Shahabi M., (2018), Assessment of the adsorption mechanism of flutamide anticancer drug on the functionalized single-walled carbon nanotube surface as a drug delivery vehicle: An alternative theoretical approach based on DFT and MD. Appl. Surf. Sci. 434: 492-503.
[17] 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. J. Mol. Liq. 255: 269-278.
[18] Shafiei F., Hashemianzadeh S. M., Bagheri Y., (2019), Insight into the encapsulation of gemcitabine into boron- nitride nanotubes and gold cluster triggered release: A molecular dynamics simulation.  J. Mol. Liq. 278: 201-212.
[19] Harismah K., Ozkendir O. M., Mirzaei M., (2020), Lithium adsorption at the C20 fullerene-Like cage: DFT approach. Adv. J. Sci. Eng. 1: 74-79.
[20] Ariaei Sh., (2020), DFT approach on arsine and phosphine gases adsorption at the surface of B16C16 nanocluster. Lab-in-Silico. 1: 44-49.
[21] Hazrati M. K., Bagheri Z., Bodaghi A., (2017), Application of C30B15N15 heterofullerene in the isoniazid drug delivery: DFT studies. Phys. E. 89: 72-76.
[22] Geng D., Yang S., Zhang Y., Yang J., Liu J., Li R., Sham T. K., Sun X., Ye S., Knights S., (2011), Nitrogen doping effects on the structure of graphene. Appl. Surf. Sci. 257: 9193-9198.
[23] Khodadadei F., Safarian S., Ghanbari N., (2017), Methotrexate-loaded nitrogen-doped graphene quantum dots nanocarriers as an efficient anticancer drug delivery system.  Mater. Sci. Eng. C. 79: 280-285.
[24] Kolosnjaj J., Szwarc H., Moussa F., (2007), Bio-Applications of Nanohan. pp.168
[25] Troshin P. A., Lyubovskaya R. N., (2008), Organic chemistry of fullerenes: The major reactions, types of fullerene derivatives and prospects for practical use. Russ. Chem. Rev. 77: 305-311.
[26] Schuster D. I., (1996), [2 + 2] Photocycloaddition of cyclic enones to C60.  J. Am. Chem. Soc., 118: 5639-5647.
[27] Ahmadi Peyghan A., YourdkhaniS., (2014), Exohedral functionalization of C60 by [4+2] cycloaddition of multiple anthracenes. Struct. Chem. 25: 785-791.
[28] Ahmadi R., Boroushaki T., Ezatti M., (2015), The usage comparison parameters, gap band energy, ∆Nmax at Xylometazoline medicine ratio its medical conveyer nano. Int. J. Nano Dimens. 6: 19-22.
[29] Rezaei-Sameti M., Ataeifar F., (2018), The theoretical study of adsorption of HCN gas on the surface of pristine, Ge, P and GeP-doped (4, 4) armchair BNNTs. Iran. Chem. Commun. 6: 280-292.
[30] Hasan M., Kumer A., Chakma U., (2020), Theoretical investigation of doping effect of Fe for SnWO4 in electronic structure and optical properties: DFT based first principle study. Adv. J. Chem. A. 3: 639-644.
[31] Ahmadi R., (2017), Study of thermodynamic parameters of (TATB) and its fullerene derivatives with different number of Carbon (C20, C24, C60) in different conditions of temperature, using density functional theory. Int. J. Nano Dimens. 8: 250-256.
[32] Nabati M., Bodaghi-Namileh V., (2020), Molecular modeling of 3-(1, 3-Dioxoisoindolin-2-yl) benzyl nitrate and its molecular docking study with phosphodiesterase-5 (PDE5).  Adv. J. Chem. A. 3: 58-69.
[33] Celaya C. A., Muñiz J., Sansoresa L. E., (2019), Structure, stability, and electronic structure properties of quasi-fullerenes Cn-q (n = 42, 48 and 60) doped with transition metal atoms (M = Sc, Ti, V and Cr): A density functional theory study. Comput. Theor. Chem. 1152: 7-19.
[34] Fekri M. H., Bazvand R., Solymani M., Razavi Mehr M., (2021), Adsorption behavior, electronical and thermodynamic properties of ornidazole drug on C60 fullerene doped with Si, B and Al: A quantum mechanical simulation. Phys. Chem. Res. 9: 151-164.
[35] Zheng Y., Shan K., Zhang Y., Gu W., (2020), Amino acid functionalized borospherenes as drug delivery systems. Biophys. Chem. 263: 106407-106423.
[36] Fekri M. H., Bazvand R., Solymani M., Razavi Mehr M., (2020), Adsorption of Metronidazole drug on the surface of nano fullerene C60 doped with Si, B and Al: A DFT study. Int. J. Nano Dimens. 11: 346-354.