Theoretical study of functionalized single-walled carbon nanotube (5, 5) with Mitoxantrone drug

Document Type : Research Paper

Authors

Department of Photonic, Institute of Science and High Technology and Environmental Sciences, Graduate University of Advanced Technology, Kerman, Iran

Abstract

Objective(s): First principles calculations were performed to study four multiple sclerosis drugs namely, Ampyra, Fingolimod, Mitoxantrone and Eliprodil in gas and liquid phases using Density Functional Theory (DFT). Computational chemistry simulations were carried out to compare calculated quantum chemical parameters for Ampyra, Fingolimod, Mitoxantrone and Eliprodil.
Materials and Methods: All calculations were performed using DMol3 code which is based on DFT.  The Double Numerical basis set with Polarization functions (DNP) was used.
Results: Mitoxantrone has highest HOMO energy, global softness, solvation energy and molecular mass and lowest LUMO energy, energy gap, global hardness and total energy in comparison to Ampyra, Fingolimod and Eliprodil in gas and solvent phases. Calculations were carried out to study the interaction of covalently binding Mitoxantrone to functionalized carbon nanotube. The Mitoxantrone local reactivity was studied through the Fukui indices in order to predict both the reactive centers and the possible sites of nucleophilic and electrophilic attacks. The Mitoxantrone binding energy  is calculated to be 6.507 eV in gas phase and -9.943 eV in solvent phase that is a decrease in BE as the drug phase changes from gas to liquid.
Conclusion: The simulation results show Mitoxantrone is quite a reactive drug. The quantum chemical parameters of pristine nanotube and f-SWNT-Mitoxantrone showed that reactivity of f-SWNT-Mitoxantrone increased in comparison to pristine nanotube in both phases.

Keywords


[1]  Compston A, Coles A. Multiple sclerosis. Lancet (London, England). 2008; 372(9648): 1502-1517.
[2]  Milo R, Kahana E. Multiple sclerosis: geoepidemiology, genetics and the environment. Autoimmun Rev. 2010; 9(5): A387-394.
[3]  Organization WH. Multiple Sclerosis International Feder- ation.(2008) Atlas: multiple sclerosis resources in the world 2008. Geneva: World Health Organization.
[4]  Mackenzie ER, Rakel B. Complementary and alternative medicine for older adults: A guide to holistic approaches to healthy aging: Springer Publishing Company; 2006.
[5]  Hirsch A. Functionalization of single walled carbon nano- tubes. Angew Chem Int Ed. 2002; 41(11): 1853-1859.
[6]  Zang J-L, Yuan Q, Wang F-C, Zhao Y-P. A comparative study of Young’s modulus of single-walled carbon nanotube by CPMD, MD and first principle simulations. Comput Mater Sci. 2009; 46(3): 621-625.
[7]  Kong J, Franklin NR, Zhou C, Chapline MG, Peng S, Cho K, Dai H. Nanotube molecular wires as chemical sensors. Science. 2000; 287(5453): 622-625.
[8]  Iijima S. Helical microtubules of graphitic carbon. Nature. 1991; 354(6348): 56-8.
[9]  Ghosh S, Sood AK, Kumar N. Carbon nanotube flow sensors. Science. 2003; 299(5609): 1042-1044.
[10] Bianco A, Kostarelos K, Prato M. Applications of carbon nanotubes in drug delivery. Curr Opin Chem Biol. 2005; 9(6): 674-679.
[11] Kong H, Zhou M, Lin G-D, Zhang H-B. Pt catalyst supported on multi-walled carbon nanotubes for hydrogenation-dearomatization of toluene and tetralin. Catal Lett. 2010; 135(1-2): 83-90. [12] Kostarelos K. Rational design and engineering of delivery systems for therapeutics: biomedical exercises in colloid and surface science. Adv Colloid Interface Sci. 2003; 106(1): 147-168.
[13] Liu Z, Chen K, Davis C, Sherlock S, Cao Q, Chen X, Dai H. Drug delivery with carbon nanotubes for in vivo cancer treatment. Cancer Res. 2008; 68(16): 6652-6660.
[14] Gallo M, Favila A, Glossman-Mitnik D. DFT studies of functionalized carbon nanotubes and fullerenes as nanovectors for drug delivery of antitubercular compounds. Chem Phys Lett 2007; 447(1): 105-109.
[15] Liu Z, Winters M, Holodniy M, Dai H. siRNA Delivery into Human T Cells and Primary Cells with Carbon Nanotube Transporters. Angew Chem Int Ed. 2007; 46(12): 2023-2027.
[16] Kam NWS, Dai H. Carbon nanotubes as intracellular protein transporters: generality and biological functionality. J Am Chem Soc. 2005; 127(16): 6021-6026.
[17] Saito R, Dresselhaus G, Dresselhaus MS. Physical properties of carbon nanotubes: World Scientific; 1998.
[18] Feazell RP, Nakayama-Ratchford N, Dai H, Lippard SJ. Soluble single-walled carbon nanotubes as longboat delivery systems for platinum (IV) anticancer drug design. J Am Chem Soc. 2007; 129(27): 8438-8439.
[19] Dhar S, Liu Z, Thomale J, Dai H, Lippard SJ. J Am Chem Soc. 2008; 130(34): 11467-11476.
[20] Pastorin G, Wu W, Wieckowski S, Briand J-P, Kostarelos K, Prato M, Prato M, Bianco A. Double functionali-               zation of carbon nanotubes for multimodal drug delivery
       Chem Comm. 2006; 11: 1182-1184.
[21] Ali-Boucetta H, Al-Jamal KT, McCarthy D, Prato M, Bianco A, Kostarelos K. Multiwalled carbon nanotube-doxorubicin supramolecular complexes for cancer therapeutics. Chem Comm. 2008(4):459-461.
[22] Liu Z, Sun X, Nakayama-Ratchford N, Dai H. Supr- amolecular chemistry on water-soluble carbon nanotubes for drug loading and delivery.  ACS Nano. 2007; 1(1): 50-56.
[23] Risi G, Bloise N, Merli D, Icaro-Cornaglia A, Profumo A, Fagnoni M, Quartarone E, Imbriani M, Visai L.RSC Advances. In vitro study of multiwall carbon nanotubes (MWCNTs) with adsorbed mitoxantrone (MTO) as a drug delivery system to treat breast cancer .2014; 4(36): 18683-18693.
[24] Delley B. An all electron numerical method for solving the local density functional for polyatomic molecules. J Chem Phys. 1990; 92(1): 508-517.
[25] Perdew JP, Wang Y. Accurate and simple analytic representation of the electron-gas correlation energy. Phys Rev B. 1992; 45(23): 13244.
[26] Chattaraj PK, Sarkar U, Roy DR. Electrophilicity index. Chem Rev. 2006; 106(6): 2065-2091.
[27] Hazarika KK, Baruah NC, Deka RC. Molecular structure and reactivity of antituberculosis drug molecules isoniazid, pyrazinamide, and 2-methylheptylisonicotinate: a density functional approach. Struct Chem. 2009; 20(6):1079-1085.
[28] Andzelm J, Kölmel C, Klamt A. Incorporation of solvent effects into density functional calculations of molecular energies and geometries. J Chem Phys. 1995; 103(21): 9312-9320.
[29] Lu X, Tian F, Xu X, Wang N, Zhang Q. A theoretical exploration of the 1, 3-dipolar cycloadditions onto the sidewalls of (n, n) armchair single-wall carbon nanotubes. J Am Chem Soc. 2003; 125(34): 10459-10464.
[30] Saikia N, Deka RC. Theoretical study on pyrazinamide adsorption onto covalently functionalized (5, 5) metallic single-walled carbon nanotube. Chem Phys Lett. 2010; 500(1): 65-70.
[31] Pantarotto D, Singh R, McCarthy D, Erhardt M, Briand JP, Prato M, Kostarelos K, Bianco A. Functionalized carbon nanotubes for plasmid DNA gene delivery. Angew Chem. 2004; 116(39): 5354-5358.