Nashrieh Shimi va Mohandesi Shimi Iran

Nashrieh Shimi va Mohandesi Shimi Iran

A Theoretical Study of Solvent Effects on 5-Fluorouracil Anticancer Drug Interaction with Adenine and Guanine

Document Type : Research Article

Authors
Leila Hokmabady 1
Heidar Raissi, 2
1 Chemistry Department, Payame Noor University, Tehran, I.R. IRAN
2 Chemistry Department, University of Birjand, Birjand, I.R. IRAN
Abstract
The interaction between the 5-fluorouracil anticancer drug and the purine bases of DNA and RNA was investigated by B3LYP method with the 6-311++G** basis set in the gas phase and water, carbon tetrachloride, acetone, and methanol solvents and the geometric parameters, the interaction energy of and the vibrational frequencies associated with hydrogen bonding have been systematically explored. In order to better understand these hydrogen-bonding interactions, Bader’s quantum theory of atoms in molecules was used and the hydrogen bonding energy was calculated by the Spinoza method. Also, single-point calculations were performed using M06-2x method with the same basis set mentioned in carbon tetrachloride and water solutions. The results showed that the interaction energy in this method has increased, but the order of stability of the hydrogen bonding complexes has not changed. It has been determined that strong hydrogen bonds are formed between monomers, which leads to changes in geometric parameters and electron structure of complexes. This subject was confirmed using electron density calculations. Comparison of the intervals and angles of hydrogen bonding showed that the hydrogen bond of N (O) B …H-NFU, in which 5FU acts as a proton donor, is stronger than the OFU … H-NB hydrogen bond. It was also observed that the hydrogen bond in the solvent with a hydrogen bond is weaker than the gas phase and the solvent without hydrogen bonding.
Keywords
5-Fluorouracil
Adenie
Guanine
DFT
Anticancer drugs

Subjects

[1] Zhao D., Zhang H., Tao W., Wei W., Sun J., He Z. A Rapid Albumin-Binding 5-Fluorouracil Prodrug with a Prolonged Circulation Time and Enhanced Antitumor Activity, Biomater. Sci. 5: 502-510 (2017)
[2] Chen L., She X., Wang T., He L., Shigdar S., Duan W., Kong L., Overcoming Acquired Drug Resistance in Colorectal Cancer Cells by Targeted Delivery of 5-FU with EGF Grafted Hollow Mesoporous Silica Nanoparticles, Nanoscale 7: 14080-14092 (2015)
[3] Wang C., Yang S., Gao L., Wang L., Cao L., Carboxymethyl Pachyman (CMP) Reduces Intestinal Mucositis and Regulates the Intestinal Microflora in 5-Fluorouracil-Treated CT26 Tumour-Bearing Mice, Food Funct. 9: 2695-2704 (2018)
[4] Thappa D.M., Senthilkumar M., Laxmisha C., Anogenital Warts – An Overview Indian J. Sex. Transm. Dis. 25: 55(2004).
[5] Hou Ewa D. N., Raczyńska D., Kamińska B. Variations of the Tautomeric Preferences and π-Electron Delocalization for the Neutral and Redox Forms of Purine when Proceeding from the Gas Phase (DFT) to Water (PCM), J Mol Model 19(9): 3947 (2013).
[6] Banerjee S., K.Mukherjee A., Interactions of the Aquated Forms of the Anticancer Drug AMD443 with DNA Purine Bases: A Detailed Computational Approach, Inorganica Chimica Acta 400: 130-141 (2013).
[7] Desta Z., Ward B.A., Soukhova N.V., Flockhart D.A., Comprehensive Evaluation of Tamoxifen Sequential Biotransformation by the Human Cytochrome P450 System in Vitro: Prominent Roles for CYP3A and CYP2D6, J. Pharmacol. Exp. Ther. 310(3): 1062-1075 (2004).
[8] Hokmabady L., Raissi H., Khanmohammadi A., Interactions of the 5-Fluorouracil. Anticancer Drug with DNA Pyrimidine Bases: A Detailed Computational Approach,  Structural Chemistry, 27(2): 487-504 (2016)
[9] Frisch M.J., 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., Ehara M., Toyota K.,  Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J.A., Peralta Jr, J.E, Ogliaro F., Bearpark M., Heyd  J.J., Brothers E., Kudin K.N., Staroverov V.N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J.C., Iyengar S.S.,  Tomasi J., Cossi M., Rega N., Millam  J.M., Klene M.,  Knox J.E.,  Cross J. B., Bakken V.,  Adamo C., Jaramillo J., Gomperts  R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J. W., Martin R.L., MorokumaK., Zakrzewski V.G., Voth G.A., Salvador P., Dannenberg  J.J., Dapprich S., Daniels A.D., Farkas O.; Foresman J.B., Ortiz J.V., Cioslowski J.,  Fox D.J., "Gaussian 03, Gaussian Inc,  Wallingford CT. (2009).
[10] Mohajeri, S., Noei, M., Salari, A., Hoseini, Z., Ahmadaghaei, N., Molaei, N. Adsorption of Phosphine on a BN Nanosurface. Iran J. Chem. Chem. Eng. (IJCCE), 37(1): 39-45 (2018).
[11] Rajaeian, E., Taherpour, A. Kinetic Study of Reaction between Allyl Compounds of Mg and Ethylene: Computational Investigation. Iran J. Chem. Chem. Eng. (IJCCE), 36(2), 7-15 (2017).
[12] Najafpour, J., Zohari, N. The Structure and Chemical Bond of FOX-7: The AIM Analysis and Vibrational Normal Modes. Iran J. Chem. Chem. Eng. (IJCCE), 30(3), 113-120 (2011).
[13] Biegler K., Schonbohm J., Derdan R., Bayles D., Bader R., AIM2000, Version
[14] Espinosa E., Molins E., Retrieving Interaction Potentials From the Topology of the Electron Density Distribution: the Case of Hydrogen Bonds, J. Chem. Phys. 113: 5686–5694 (2000).
[15] Khorram R., Raissi H., Shahabi M., Analysis of the Structures, Energetics, and Vibrational Frequencies for the Hydrogen-Bonded Interaction of Nucleic Acid Bases with Carmustine Pharmaceutical Agent: A Detailed Computational Approach, Structural Chemistry 29: 1165–1174 (2018).
[16] Miertus S., Tomasi J., Electrostatic Interaction of a Solute with a Continuum. A Direct Utilization of AB Initio Molecular Potentials for the Prevision of Solvent Effects, Chem Phys 55:117-129 (1981).
[17] Klamt A., Moya C., Palomar J., A Comprehensive Comparison of the IEFPCM and SS(V)PE Continuum Solvation Methods with the COSMO Approach, Journal of Chemical Theory and Computation, 11:  4220-4225 (2015).
[18] Boys S.F., Bernardi F., The Calculation of Small Molecular Interactions by the Differences of Separate Total Energies. Some Procedures with Reduced Errors, MolPhys 19: 553-566 (1970).
[19]  Saccone M.,  Siiskonen A.,  Fernandez-Palacio F.,  Priimagi A., Terraneo G.,  Resnati G.,  Metrangolo P., Halogen Bonding Stabilizes a Cis-Azobenzene Derivative in the Solid State: A Crystallographic Study, Acta Cryst. B, 73:  227-233 (2017).
[20] Parra R.D., Ohlssen J., Cooperativity In Intramolecular Bifurcated Hydrogen Bonds: An AB Initio Study, J. Phys. Chem. A 112: 3492-34998 (2008).
[21] Zio´1kowski M., Grabowski S.J., Leszczynski J., Cooperativity in Hydrogen-Bonded Interactions:  Ab Initio and “Atoms in Molecules” Analyses, J. Phys. Chem. A 110: 6514-6521 (2006).
[22]  Hosseinian A.,  Vessally E.,  Babazadeh M.,  Edjlali L.,  Es’haghi M., Noncovalent Interactions in 1:1 Complexes of Nitrogen Trifluoride and Nitroxyl, THEOCHEM, 16: 1750060 (2017).