Relaxations of methylpyridinone tautomers at the C60 surfaces: DFT studies

Document Type : Reasearch Paper


1 Department of Medicinal Chemistry, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, Iran

2 Department of Physics, Faculty of Science, Bilkent University, Ankara, Turkey


Density functional theory (DFT) based calculations have been performed to examine the relaxations of tautomers of 4–hydroxy–6–methylpyridin–2(1H)–one (MPO), as a representative of pyridinone derivatives, at the fullerene (C60) surfaces. Optimized molecular properties including energies, dipole moments and atomic scale quadrupole coupling constants (CQ) have been evaluated to investigate the structural and electronic properties of the models. The structural configurations of tautomers show different relaxations at the C60 surface yielding different magnitudes of total and binding energies. Moreover, deformation of each tautomer due to relaxation at the C60 surface with respect to the initial singular structure has been examined. Complimentary parameters of energy gaps and dipole moments exhibit the effects of relaxations at the C60 surface for the MPO counterparts. Atomic scale CQ properties also indicate that the electronic properties of atoms show significant changes for tautomers and hybrid systems. As a final note, the tautomeric structures in singular and hybrid forms exhibit different electronic properties because of effects of interactions with C60, especially for the interaction regions.


Main Subjects

 [1] Ma Y., Kong X., Abbate V., Hider R. C., (2015), Synthesis and characterization of novel iron specific bicyclic fluorescent probes. Sens. Actuat. B. 213: 12-19.
[2] Upanan S., Pangjit K., Uthaipibull C., Fucharoen S., McKie A. T., Srichairatanakool S., (2015), Combined treatment of 3–hydroxypyridine–4–one derivatives and green tea extract to induce hepcidin expression in iron–overloaded β–thalassemic mice. Asian Pacific J. Trop. Biomed. 5: 1010–1017.
[3] Andayi W. A., Egan T. J., Chibale K., (2014), Kojic acid derived hydroxypyridinone–chloroquine hybrids: Synthesis, crystal structure, antiplasmodial activity and β–haematin inhibition. Bioorg. Med. Chem. Lett. 24: 3263–3267.
[4] Medina–Franco J. L., Martínez–Mayorga K., Juárez–Gordiano C., Castillo R., (2007), Pyridin–2(1H)–ones: A promising class of HIV–1 non–nucleoside reverse transcriptase inhibitors. Chem. Med. Chem. 2: 1141–1147.
[5] De Clercq E., (2005), New approaches toward anti–HIV chemotherapy. J. Med. Chem. 48: 1297–1313.
[6] Reyes H., Aguirre G., Cháveza D., (2013), 4–Hydroxy–6–methylpyridin–2(1H)–one. Acta Cryst. E. 69: 1534-1538.
[7] Mohammadpour M., Zborowski K. K., Heidarpoor S., Żuchowski G., Proniewicz L. M., (2016), Modeling of stability and properties of anionic and cationic tautomers of the 3-hydroxypyridin-4-one system. Comput. Theor. Chem. 1078: 96-103.
[8] Yaraghi A., Ozkendir O. M., Mirzaei M., (2015), DFT studies of 5–fluorouracil tautomers on a silicon graphene nanosheet. Superlatt. Microstruct. 85: 784–788.
[9] Graff M., Dobrowolski J. C., (2013), On tautomerism of diazinones. Comput. Theor. Chem. 1026: 55–64.
[10] Siddiqui S. A., Bouarissa N., Rasheed T., Al–Assiri M. S., Al–Hajry A., (2014), Detection of electronically equivalent tautomers of adenine base: DFT study. Mater. Res. Bull. 51: 309–314.
[11] Garmaroudi F. S., Vahdati R. A. R., (2010), Functionalized CNTs for delivery of therapeutics. Int. J. Nano Dimens. 1: 89–102.
[12] Mirzaei M., (2013), Effects of carbon nanotubes on properties of the fluorouracil anticancer drug: DFT studies of a CNT-fluorouracil compound. Int. J. Nano Dimens. 3: 175–179.
[13] Mundra R. V., Wu X., Sauer J., Dordick J. S., Kane R. S., (2014), Nanotubes in biological applications. Curr. Opin. Biotechnol. 28: 25–32.
[14] Bodaghi A., Mirzaei M., Seif A., Giahi M., (2008), A computational NMR study on zigzag aluminum nitride nanotubes. Physica E. 41: 209–212.
[15] Rahimnejad S., Mirzaei M., (2011), Computational studies of planar, tubular and conical forms of silicon nanostructures. Int. J. Nano Dimens. 1: 257–260.
[16] Ahmadi R., Boroushaki T., Ezzati M., (2015), The usage comparison of occupancy parameters, gap band energy, ΔNmax at Xylometazoline medicine ratio its medical conveyer nano. Int. J. Nano Dimens. 6: 19-22.
[17] Ema M., Gamo M., Honda K., (2016), A review of toxicity studies of single–walled carbon nanotubes in laboratory animals. Regul. Toxicol. Pharmacol. 74: 42–63.
[18] Marmolejo–Tejada J. M., Velasco–Medina J., (2016), Review on graphene nanoribbon devices for logic applications. Microelectron. J. 48: 18–38.
[19] Linko V., Ora A., Kostiainen M. A., (2015), DNA nanostructures as smart drug–delivery vehicles and molecular devices. Trends Biotechnol. 33: 586–594.
[20] Rezvani M., Ganji M. D., Faghihnasiri M., (2013), Encapsulation of lamivudine into single walled carbon nanotubes: A vdW–DF study. Physica E. 52: 27–33.
[21] Mirzaei M., (2013), Uracil–functionalized ultra–small (n, 0) boron nitride nanotubes (n = 3–6): Computational studies. Superlatt. Microstruct. 57: 44–50.
[22] Ahmadian N., Ganji M. D., Laffafchy M., (2012), Theoretical investigation of nerve agent DMMP adsorption onto Stone–Wales defected single–walled carbon nanotube. Mater. Chem. Phys. 135: 569–574.
[23] Zhao J., Ma J., Nan X., Tang B., (2016), Application of non–covalent functionalized carbon nanotubes for the counter electrode of dye–sensitized solar cells. Org. Electron. 30: 52–59.
[24] Mirzaei M., (2013), Formation of a peptide assisted bi–graphene and its properties: DFT studies. Superlatt. Microstruct. 54: 47–53.
[25] Das T. P., Han E. L., (1958), Nuclear Quadrupole Resonance Spectroscopy. Academic Press, New York.
[26] Mirzaei M., Gulseren O., (2015), DFT studies of CNT–functionalized uracil–acetate hybrids. Physica E. 73: 105–109.
[27] Mirzaei M., Samadi Z., Hadipour N. L., (2010), Hydrogen bonds of peptide group in four acetamide derivatives: DFT study of oxygen and nitrogen NQR and NMR parameters. J. Iran. Chem. Soc. 7: 164–170.
[28] Seif A., Boshra A., Mirzaei M., Aghaie M., (2008), Carbon–substituting in (4, 4) boron nitride nanotube: Density functional study of boron–11 and nitrogen–14 electric field gradient tensors. J. Theor. Comput. Chem. 7: 447–455.
[29] Mirzaei M., Hadipour N. L., Abolhassani M. R., (2007), Influence of C-doping on the B-11 and N-14 quadrupole coupling constants in boron-nitride nanotubes: A DFT study. Z. Naturforsch. A. 62: 56–60.
[30] Mirzaei M., Elmi F., Hadipour N. L., (2006), A systematic investigation of hydrogen-bonding effects on the 17O, 14N, and 2H nuclear quadrupole resonance parameters of anhydrous and monohydrated cytosine crystalline structures: A density functional theory study. J. Phys. Chem. B. 110: 10991–10996.
[31] Pyykkö P., (2001), Spectroscopic nuclear quadrupole moments. Mol. Phys. 99: 1617–1629.
[32] Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., (2009), Gaussian 09, A.01.  Gaussian Inc, Pittsburgh, PA.
[33] The Gaussian IOps Manual,
[34] Grimme S., (2011), Density functional theory with London dispersion corrections. WIREs Comput. Molec. Sci. 1: 211–228.