Theoretical studies on photo-induced electron transfer process on [Thioridazine].C60 nano-complex; a first principle DFT and TD-DFT

Document Type : Article

Authors

1 - Faculty of Chemistry, Razi University, Kermanshah, P.O. Box 6714967346, Iran. - Medical Biology Research Center, Kermanshah University of Medical Sciences, Kermanshah, Iran

2 Faculty of Chemistry, Razi University, Kermanshah, P.O. Box 6714967346, Iran

3 Young Researchers and Elite Club, Kermanshah Branch, Islamic Azad University, Kermanshah, Iran

10.24200/sci.2020.53361.3203

Abstract

In this study, using the density functional theory (DFT) and time dependent density functional theory (TD-DFT) methods, the physical and chemical properties of the Thioridazineand fullerene C60 nano complex were studied. The most important goal was increasing C60 dipolar moment as a novel drug delivery system to carry Thioridazineand. Several descriptors were used in the ground state, including electrochemical properties based on the HOMO and LUMO orbital energy, hardness, softness, chemical potential, and Mulliken charge. The dipole moment of this nano-complex is about 2.61D, which indicates its moderate solubility in polar solvents. The UV-Vis spectrum obtained with the CAM-B3LYP method shows that the absorption spectrum has blue-shifted by about λ = 24 nm after formation of the complex. Based on the calculations in the excited state and the hole-electron theory in the first three modes, a photo-induced electron transfer (PET) phenomenon was observed at different absorption wavelengths for the complex. Using the Marcus theory of electron transfer, the free energy of activation for electron transfer and the free energy of electron transfer for all PETs were calculated.

Keywords


References:
[1] Chien, Y. “Novel drug delivery systems”, Informa Health Care, (1991).
[2]  Freeman, A. I and  Mayhew, E. “Targeted drug delivery”, Cancer, 58, pp. 573-583(1986) .
[3]  Mills, J. K and  Needham, D. “Targeted drug delivery”, Expert Opinion on Therapeutic Patents, 9. pp. 1499-1513 (1999).
[4]  Allen, T. M and  Cullis, P.R. “Drug delivery systems: entering the mainstream”, Science, 303. pp. 1818-1822 (2004).
[5] Singh, R and Lillard, J. W. “Nanoparticle-based targeted drug delivery”, Exp. Mol. Pathol, 86. pp. 215-223 (2009).
[6] Sun, X., Liu, Z., Welsher, K., et al. “Nano-graphene oxide for cellular imaging and drug delivery”, Nano research, 1. pp. 203-212(2008) .
[7] Mishra, B., Patel, B. B and Tiwari, S. “Colloidal nanocarriers: a review on formulation technology, types and applications toward targeted drug delivery”, Nanomed. Nanotechnol. Biol. Med, 6. pp. 9-24 (2010).
[8] Koo, O. M., Rubinstein, I and Onyuksel, H. “Role of nanotechnology in targeted drug delivery and imaging: a concise review”, Nanomed. Nanotechnol. Biol. Med, 1. pp. 193-212(2005) .
[9] Nasongkla, N., Bey, E., Ren, J., etal. “Multifunctional polymeric micelles as cancer-targeted, MRI-ultrasensitive drug delivery systems”, Nano Letters, 6. pp. 2427-2430(2006)  .
[10] Kropp, Sundelof, H., Hajdu, R., et al. “Metabolism of thienamycin and related carbapenem antibiotics by the renal dipeptidase”, dehydropeptidase-I, Antimicrobial agents and chemotherapy, 22. pp. 62-70 (1982).
[11] Price-Whelan, A.,  Dietrich, L. E and Newman, D. K. “Rethinking'secondary'metabolism: physiological roles for phenazine antibiotics”, Nat. Chem. Biol, 2. pp. 71(2006) .
[12] Jurima-Romet, M., Crawford, K., Cyr, T., et al. “Terfenadine metabolism in human liver. In vitro inhibition by macrolide antibiotics and azole antifungals”, Drug Metab. Disposition, 22. pp. 849-857  (1994).
[13] Farokhzad, O. C and Langer, R. “Impact of nanotechnology on drug delivery”, Acs Nano, 3. pp. 16-20 (2009).
[14] Shi, J., Votruba, A.R., Farokhzad, O. C and Langer, R. “Nanotechnology in drug delivery and tissue engineering: from discovery to applications”, Nano Letters, 10. pp. 3223-3230  (2010).
[15]  Taherpour, A.A., Zolfaghar, N., Jamshidi, M., Jalilian, J., et al. “Structural distortions of fullerene C60n (n= 0 to− 6) by first principle density functional theory”, Journal of Molecular Structure, 1184. pp. 546-556 (2019) .
[16] Bianco, A., Kostarelos, K and Prato, M. “Applications of carbon nanotubes in drug delivery, Curr. Opin. Chem”. Biol, 9. pp. 674-679 (2005).
[17] Liu, Z., Chen, K., Davis, C., et al. “Drug delivery with carbon nanotubes for in vivo cancer treatment”, Cancer Res, 68. pp. 6652-6660 (2008).
[18] Hughes, G. A. “Nanostructure-mediated drug delivery”, Nanomed. Nanotechnol. Biol. Med, 1. pp. 22-30 (2005).
[19] Cataldo, F., Da Ros, T. “Medicinal chemistry and pharmacological potential of fullerenes and carbon nanotubes”, Springer Science & Business Media, 2008.
[20] Bakry, R., Vallant, R. M., Najam-ul-Haq, M.,et al. “Medicinal applications of fullerenes”, International journal of nanomedicine, 2. pp. 639  (2007).
[21] Harhaji, L., Isakovic, A., Raicevic, N., et al. “Multiple mechanisms underlying the anticancer action of nanocrystalline fullerene”, Eur. J. Pharmacol, 568. pp. 89-98 (2007).
[22] Brunet, L. N., Lyon, D. Y., Hotze, E. M., et al. “Comparative photoactivity and antibacterial properties of C60 fullerenes and titanium dioxide nanoparticles”, Environmental science & technology, 43. pp. 4355-4360 (2009).
[23] Lyon, D. Y., Adams, L. K., Falkner, J. C., et al. “Antibacterial activity of fullerene water suspensions: effects of preparation method and particle size”, Environmental science & technology, 40. pp. 4360-4366 (2006)  .
[24]  Erb, T., Zhokhavets, U., Gobsch, U., et al. “Correlation between structural and optical properties of composite polymer/fullerene films for organic solar cells”, Adv. Funct. Mater, 15. pp. 1193-1196  (2005).
[25] Scharber, M., Schultz, N., Sariciftci, N., et al. “Optical-and photocurrent-detected magnetic resonance studies on conjugated polymer/fullerene composites”, Physical Review B, 67. pp. 085202 (2003).
[26] Hosseinian, A., Vessally, E., Yahyaei, S., et al.  “A Density Functional Theory Study on the Interaction Between 5-Fluorouracil Drug and C24 Fullerene”, JCS,  1-12.
[27] Samanta, P. N and  Das, N. N. “Noncovalent interaction assisted fullerene for the transportation of some brain anticancer drugs: A theoretical study”, Journal of Molecular Graphics and Modelling, 72. pp. 187-200 (2017).
[28] Gong, P., Zhang, L., Yuan, X. A., et al.  “Multifunctional fluorescent PEGylated fluorinated graphene for targeted drug delivery: An experiment and DFT study”, Dyes and Pigments, 162. pp. 573-582 (2019).
[29] Teixeira, T. A. R.,  Costa, L. A. S and Sant'Ana, A. C. “A proposal for the adsorption of anastrozole anticancer drug on gold nanoparticle surfaces”, Journal of Raman Spectroscopy, 0.
[30] Taherpour, A.A., Jamshidi, M and Rezaei, O. “DFT and TD-DFT theoretical studies on photo-induced electron transfer process on [Cefamandole]. C60 nano-complex”, Journal of Molecular Graphics and Modelling, 75. pp. 42-48 (2017).
[31] Wazzan, N and  Safi, Z. “DFT calculations of the tautomerization and NLO properties of 5-amino-7-(pyrrolidin-1-yl)-2,4,4-trimethyl-1,4-dihydro-1,6-naphthyridine-8-carbonitrile (APNC)”, Journal of Molecular Structure.
[32] Jamshidi, M., Rezaei, O., Belverdi, A. R., et al.  “A highly selective fluorescent chemosensor for Mg 2+ ion in aqueous solution using density function theory calculations”, Journal of Molecular Structure, 1123. pp.  111-115 (2016).
[33] An, B., Yuan, H.,  Zhu, Q., et al. “Theoretical insight into the excited-state intramolecular proton transfer mechanisms of three amino-type hydrogen-bonding molecules”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 175. pp. 36-42  (2017).
[34] Yuan, H., Feng, s., Wen, K., et al.  “A quantum-chemical insight into the tunable fluorescence color and distinct photoisomerization mechanisms between a novel ESIPT fluorophore and its protonated form”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 183. pp. 123-130 (2017).
[35] Taherpour, A.A., Jamshidi, M and Rezaei, O. “Recognition of switching on or off fluorescence emission spectrum on the Schiff-bases as a Mg2+ chemosensor: A first principle DFT and TD-DFT study”, Journal of Molecular Structure, 1147. pp. 815-820 (2017).
[36] Harriman, A.,  Kubo, Y and Sessler, J. L. “Molecular recognition via base pairing: photoinduced electron transfer in hydrogen-bonded zinc porphyrin-benzoquinone conjugates”, Journal of the American Chemical Society, 114. pp. 388-390  (1992).
[37]  Reisner, E.,  Arion, V. B., Keppler, B. K., et al.  “Electron-transfer activated metal-based anticancer drugs”, Inorg. Chim. Acta, 361. pp. 1569-1583  (2008).
[38] Taherpour, A.A. “Theoretical and Quantitative Structural Relationship Study of the Electrochemical Properties of [M2@ C x]@[SWCNT (5, 5)-Armchair-C n H20](M= Er and Sc, x= 82 and 84, and n= 20− 300) Complexes”, The Journal of Physical Chemistry C, 113. pp. 5402-5408  (2009).
[39] Carlsson, A., Roos, B. E., Wålinder, J., et al. “Further studies on the mechanism of antipsychotic action: Potentiation by α-methyltyrosine of thioridazine effects in chronic schizophrenics”, J. Neural Transm, 34. pp. (1973) 125-132 (1973).
[40] Gholivand, K.,  Hosseini, M., Maghsoud, Y., et al. “Relations between Structural and Luminescence Properties of Novel Lanthanide Nitrate Complexes with Bis-phosphoramidate Ligands, Inorganic Chemistry”, (2019).
[41] Patel, R. N and Singh, Y. P. “Synthesis, structural characterization, DFT studies and in-vitro antidiabetic activity of new mixed ligand oxovanadium(IV) complex with tridentate Schiff base”, Journal of Molecular Structure, 1153. pp. 162-169  (2018).
[42] Zara, Z.,   Iqbal, J.,  Ayub, K., et al. “A comparative study of DFT calculated and experimental UV/Visible spectra for thirty carboline and carbazole based compounds”, Journal of Molecular Structure, 1149. pp. 282-298(2017) .
[43] 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”, International Journal of Nano Dimension, 8. pp 250-256  (2017).
[44]  Srivastava, A. K.,  Kumar, A and  Misra, N. “Superalkali@ C60− superhalogen: Structure and nonlinear optical properties of a new class of endofullerene complexes”, Chemical Physics Letters, 682. pp. 20-25 (2017) .
[45] Sutradhar, S and  Patnaik, A. “A new fullerene-C60–Nanogold composite for non-enzymatic glucose sensing”, Sensors and Actuators B: Chemical, 241. pp. 681-689  (2017).
[46] Dhiman, s.,  Kumar, R and  Dharamvir, K. “DFT study of Cu and Ag clusters inside C60”, Journal of Molecular Structure, 1100. pp. 328-337 (2015)  .
[47] Taherpour, A.A.,  Jamshidi, M., Rezaei, O., et al. A.R.  “Photoinduced electron transfer process on emission spectrum of N,N′-bis(salicylidene)-1,2-phenylenediamine as a Mg2+ cation chemosensor: A first principle DFT and TDDFT study”, Journal of Molecular Structure, 1161. pp. 339-344  (2018).
[48] Taherpour, A.A.,  Shahri, Z.,  Rezaei, O., et al.  “Adsorption, intercalation and sensing of helium on yttrium functionalized open edge boron nitride: A first principle DFT and TDDFT study”, Chemical Physics Letters, 691. pp. 231-237 (2018).
[49] Wagner, F. R.,  Bezugly, V.,  Kohout,M and  Grin, Y. “Charge decomposition analysis of the electron localizability indicator: a bridge between the orbital and direct space representation of the chemical bond”, Chemistry-A European Journal, 13. pp. 5724-5741 (2007) .
[50] Paredes-Gil, K and  Jaque, P. “Initiation stage of alkene metathesis: Insights from natural bond orbital and charge decomposition analyses”, Chemical Physics Letters, 618. pp. 174-181  (2015).
[51] Rajesh, P.,  Kandan, P.,  Sathish, S.,  Manikandan, A., et al. “Vibrational spectroscopic, UV–Vis, molecular structure and NBO analysis of Rabeprazole”, Journal of Molecular Structure, 1137 . pp. 277-291  (2017).
[52] Taherpour, A.A.,  Rezaei, O.,  Shahri, Z., et al. “First principles studies of electronic and optical properties of helium adsorption on Sc-doped BN monolayer”, Journal of the Iranian Chemical Society, 12. pp. 1983-1990 (2015).
[53] Srivastava, R.,  Al-Omary, F. A. M.,  El-Emam,  A. A.,et al. “A combined experimental and theoretical DFT (B3LYP, CAM-B3LYP and M06-2X) study on electronic structure, hydrogen bonding, solvent effects and spectral features of methyl 1H-indol-5-carboxylate”, Journal of Molecular Structure, 1137. pp. 725-741  (2017).
[54] Scheiner, S and Duan, X. “Applicability of the Marcus equation to proton transfer in symmetric and unsymmetric systems”, Journal of Molecular Structure: THEOCHEM, 285 . pp. 27-32  (1993).
[55]  Shamsipur, M., Barati, A., Taherpour, A.A.,et al. “Resolving the multiple emission centers in carbon dots: from fluorophore molecular states to aromatic domain states and carbon-core states”, The journal of physical chemistry letters, 9. pp. 4189-4198(2018) .
[56]  Taherpour, A.A. and Maleki-Noureini, M. “Free Energies of Electron Transfer, Electron Transfer Kinetic Theoretical and Quantitative Structural Relationships and Electrochemical Properties Studies of Gadolinium Nitride Cluster Fullerenes Gd3N@Cn in [X-UT-Y][Gd3N@Cn](n = 80, 82, 84, 86 and 88) Supramolecular Complexes”, Fullerenes, Nanotubes and Carbon Nanostructures, 21. pp. 485-502  (2013).