Adsorption of melphalan anticancer drug on the surface of fullerene (C24): a comprehensive DFT study

Document Type : Research Paper


Department of Chemistry, Islamic Azad University, Yadegar-e-Imam Khomeini (RAH) Shahre-Rey Branch, Tehran, Iran


Objective (s): The present study aimed to assess the adsorption of fullerene C24 with Melphalan anticancer agent in a solvent phase (water) at the B3LYP/6-31G (d) theoretical level.
Materials and Methods: Initially, the structures of Melphalan and fullerene complexes were optimized in four configurations. Afterwards, IR calculations and molecular orbital analysis were performed. In addition, some important parameters were assessed, including the adsorption energy, Gibbs free energy changes (ΔGad), enthalpy (ΔHad) variations, thermodynamic equilibrium constant, specific heat capacity, chemical hardness, energy gap, and electrophilicity.
Results: According to the results, Gibbs free energy changes (ΔGad), enthalpy (ΔHad) variations, III-Isomer, and IV-Isomer were negatives at various temperatures, while for I-Isomer and II-Isomer were positives throughout the temperature range of 298.15-310.15 K.
Conclusion: Since according to the obtained results for adsorption of Melphalan on the C24 in , III-Isomer, and IV-Isomer were spontaneous at various temperatures, while I-Isomer and II-Isomer were not spontaneous throughout the temperature range of 298.15-310.15 K.
Conclusion: Since the adsorption of Melphalan with fullerene C24 is spontaneous. Moreover, the effects of temperature on thermodynamic parameters were investigated, and the calculated specific heat capacity values indicated that C24 could be utilized as a sensing material in the construction of thermal biosensors for Melphalan determination.


1. Tian J, Zhang D, Liu G, Zhao L. Utilizing fullerene-induced polymer spherulites as controlled drug delivery systems.J Control Release. 2013; 172(2): 45-50.
2. Simon F, Peterlik H, Pfeiffer R, Bernardi J, Kuzmany H. Fullerene release from the inside of carbon nanotubes: A possible route toward drug delivery. Chem Phys Lett. 2007; 445(2): 288-292.
3. Gallo M, Favila A, Mitnik D. G. DFT studies of functionalized carbon nanotubes and fullerenes as nanovectors for drug delivery of antitubercular compounds .Chem. Phys Lett. 2007; 447(1): 105-109.
4. Ahmadi R, Mada hzadeh Darini N. Study of 5-Picrylamino-1,2,3,4-tetrazole (PAT) with nanostructures of fullerene and boron nitride nano-cages in different conditions of temperature, using density functional theory.Int J Bio-Inorg Hybrid Nanomater. 2016; 5(4): 273-278.
5. Ahmadi R, Boroushaki T, Ezzati M. Computational Study of Chemical Properties of Xylometazoline and the Connected form to Fullerene (C60) as a Medicine Nano Carrier. In. J Bio-Inorg Hybd Nanomat.2014; 3(1): 23-27.
6. Ahmadi R, Shemshaki L. The synthesis of α, 2, 4, 6-tetranitrotoluene from the reaction of 2, 4, 6-trinitrotoluene (TNT) with Fluorotrinitromethane in different temperature conditions.the DFT method. AM J O Chem Tech. 2017; 5(1): 6-11.
7. Shi J, Liu Y, Wang L, Gao J, Zhang J, Yu X, Ma R., Liu R, Zhang Z. A tumoral acidic pH-responsive drug delivery system based on a novel photosensitizer (fullerene) for in vitro and in vivo chemo-photodynamic therapy. Acta Biomater. 2014; 10(3): 1280-1291.
8. Hazrati M. K, Hadipour N. Adsorption behavior of 5-fluorouracil on pristine, B-, Si-, and Al-doped C60 fullerenes: A first-principles study. Phys Lett. 2016; 380 (7-8):937-941.
9. Naderi E, Mirzaei M, Saghaie L, Khodarahmi G, Gülseren O. Relaxations of methylpyridinone tautomers at the C60 surfaces: DFT studies. Int J Nano Dimens. 2016; 8(2): 124-131.
10. Ahmadi R, Pirahan-Foroush M. Ab initio studies of fullerene effect on chemical properties of naphazoline drop. Ann Mil Health Sci Res: 2014; 12(2): 86-90.
11. R. Ahmadi, M.R. Jalali Sarvestani, Iranian Chemical Communication, 2019, 7(1), 344-351.
12. Ahmadi R, Soleymani R, Yousofzad T. Study on effect of addition of nicotine on nanofullerene structure C60 as a medicine nanocarrier. Orient J Chem.2012; 28(2):773-779.
13. Chigo-Anota E, Escobedo-Morales A, Hernández-Cocoletzi H, Lópezy-López J. G. Nitric oxide adsorption on non-stoichiometric boron nitride fullerene: Structural stability, physicochemistry and drug delivery perspectives. Physica E Low Dimens Syst Nanostruct. 2007; 74(C):538-543.
14. Mullett W. M. Determination of drugs in biological fluids by direct injection
of samples for liquid-chromatographic analysis. J Biochem Biophys Methods.2007; 70(2): 263-273.
15. Chollet D. F. Determination of antiepileptic drugs in biological material. J Chromatogr B. 2007; 767(2): 191-233.
16. Ahmadi R, Rezaei asl A. Computational study of Chemical properties in fullerene Derivatives of Enalapril drug. Int J New Chem. 2015; 2(1):189-198.
17. Sadeghi B, Vahdati R. A. R. Comparison and SEM-characterization of novel solvents of DNA/carbon nanotube. Appl Surf Sci. 2012; 258(7): 3086-3088.
18. Verster J. C, Volkerts E. R. Antihistamines and driving ability: evidence from on-the-road driving studies during normal traffic. Ann. Allergy. Asthma Immunol.2004; 92(3): 294-304.
19. Baciu T, Botello I, Borrull F, Calull M, Aguilar C. Capillary electrophoresis and related techniques in the determinationof drugs of abuse and their metabolites. Trends Anal Chem. 2015; 74(1): 89-108.
20. Moeller M. R, Steinmeyer S, Kraemer T.Determination of drugs of abuse in blood. J. Chromatogr. B. 1998; 713(1): 91-109.
21. Bashiri S, Vessally E, Bekhradnia A, Hosseinian A, Edjlali L. Utility of extrinsic [60] fullerenes as work function type sensors for amphetamine drug detection: DFT studies. Vacuum. 2016; 136(1): 156-162.
22. Vytras K. The use of ion-selective electrodes in the determination of drug substances. J. Pharm Biomed Anal. 2002; 7(1): 789-812.
23. Li W, Li G, Lu X, Ma J, Zeng P, He Q, Wang Y. Strong adsorption of Al-doped carbon nanotubes toward cisplatin. Chem Phys Lett. 2016; 658(1): 162-167.
24. Ahmadi R, Jalali Sarvestani MR, Sadeghi B, Computational study of the fullerene effects on the properties of 16 different drugs: A review. Int J Nano Dimens. 2018; 9 (4): 325-335
25. Ahmadi R, Mirkamali E. S. Determination of thermodynamic parameters of produced materials from (ATTz) with boron nitride nano-cages in different conditions of temperature, with DFT method. J. Phys Theor. Chem IAU Iran. 2016; 13(1): 297-302.
26. Gökpek Y,Bilge M, Bilge D, Alver Ö, Parlak C. Adsorption mechanism, structural and electronic properties: 4-Phenylpyridine & undoped or doped (B or Si) C60. J Mol Liq. 2016; 238(1): 225-228.
27. Ahmadi R, Boroushaki T, Ezzati M. The usage comparison of occupancy parameters, gap band energy, ΔNmax at xylometazoline medicine ratio its medical conveyer nano. Int J Nano Dimens. 2015; 6(1): 19-22.
28. Ahmadi R, Pirahan-Foroush M. Fullerene effect on chemical properties of antihypertensive clonidine in water phase. Ann.  Mil Health Sci Res. 2015; 12(1): 39-43.
29. Stern G. Focus on Levodopa. J Neurol Sci. 1974; 22(1):521-527.
30. Ahmadi R. 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.2017; 8 (3): 250-256
31. Houston M. C. (1981), Clonidine hydrochloride: Review of pharmacologic and clinical aspects. Prog Cardiovasc Dis.1981; 23(1): 337-350.
32. Nally J. V, Black H. R. State-of-the-art review: Captopril renography—Pathophysiological considerations and clinical observations. Semin Nucl Med.1992; 22(2):85-97.
33. Ahmadi R, Salmaniha, M. Investigation of Chemical Properties in Fullerene Derivatives of Fluoxetine Drug: A DFT Study. Int J New Chem. 2015; 4(1):152-160.
34. Rodman J. S, Deutsch D. J, Gutman S. I. Methyldopa hepatitis: A report of six cases and review of the literature, AM J Medi.1976; 60(1):941-948.
35. Ahmadi R. Computational study of chemical properties of Captopril drug and the connected form to Fullerene (C60) as a medicine nano carrier. J Phys Theor Chem IAU, Iran. 2012; 9(1): 185-190.
36. Ahmadi R, Pourkarim S. Investigation of Fullerene (C60) Effects on Chemical Properties of Metoprolol: A DFT Study. Int J Bio-Inorg Hybd Nanomat. 2015; 4(1): 249-254.