Theoretical study of 8-Hydroxyquinoline with fullerenes and carbon nanotubes as drug delivery nanocarriers

Number of pages: 104 File Format: word File Code: 31900
Year: 2014 University Degree: Master's degree Category: Chemical - Petrochemical Engineering
  • Part of the Content
  • Contents & Resources
  • Summary of Theoretical study of 8-Hydroxyquinoline with fullerenes and carbon nanotubes as drug delivery nanocarriers

    Dissertation for Master's Degree

    Field: Chemistry, Major: Organic

    Abstract

    In recent years, the use of nanotubes as nanocarriers for drug delivery has been investigated. In this research, fullerene C60 and nine different nanotubes have been used as carriers of the drug molecule 8-hydroxyquinoline. First, the structure of HQ-8 drug molecule and nanotubes were drawn by NanotubeModeler and GaussView software, and then optimized by Gaussian09 software. After that, the 8-HQ molecule was placed on the surface of different nanotubes from both sides of its heteroatoms, i.e. pyridinium nitrogen atom and hydroxyl group, and their structure was also optimized by the mentioned method. The results, including information related to binding energy, dipole moment, atomic charges, bond angles and lengths, fundamental properties (ion potential, electron withdrawing, chemical potential, hardness and softness) and HOMO-LUMO energy gap, were calculated and evaluated. In terms of binding energy and absorption rate, CNT(9,0) nanotube has the best interaction with the drug molecule 8-HQ from the side of the nitrogen atom. has pyridine. Also, in terms of dipole moment, BNNTdopedGe nanotube has shown the highest dipole moment with 8-HQ molecule. The structure of this nanotube with the 8-HQ molecule (especially from the side of the N atom) has shown greater polarizability and charge transfer than other structures. rtl;"> 

    Chapter One

    Nanotechnology

    1-1) Introduction

    Nanotechnology is a range of technology in which humans can create all kinds of compounds, alloys, devices and tools and, in general, systems Design and build various structures in atomic and molecular scale and in nanometer dimensions (one billionth of a meter). In most cases, the manufacturing method is in the form of moving atoms and molecules and placing them in appropriate positions [1].

    1-2) History of nanotechnology

    The use of nanotechnology by humans has a long history, contrary to popular belief. In this regard, there is evidence that the blue color used by the Maya is nanostructured. After that, the Romans used these materials to make cups with vivid colors. In this way, they used gold particles to color these cups. An example of these cups, which was discovered for the first time, is the Lycurgus cup, which belongs to the fourth century BC and has nanometer particles of gold and silver that show different colors when exposed to different lights. However, the scientific story of nanotechnology is something else. One of the first scientific reports in this regard is the report on the production of colloid gold particles in 1857 by Michael Faraday. Later, carbon black was used as an additive to color and strengthen rubber. The use of catalysts with nanometer structure started 70 years ago [1].

    In 1991, a Japanese scientist named Sumio Ijima[1] accidentally discovered and produced a structure of carbon. According to its shape, the corresponding product was called carbon nanotube. In a carbon nanotube, carbon atoms are arranged in a cylindrical structure. The arrangement of carbon atoms in the wall of this cylindrical structure is similar to the arrangement of carbon atoms in the graphite sheet. When a graphite layer is wrapped, a carbon nanotube is formed. In fact, carbon nanotube is graphite that has become a tube at the nano scale [2].

    1-3) Other forms of carbon

    Carbon is the most amazing element of nature, so that organic chemistry is known as the chemistry of carbon compounds. Also, polymer engineering is based on the carbon element.Other forms of carbon are: graphite, diamond, nanotube and fullerene. In all of these materials, carbon atoms are connected by strong covalent bonds so that they are considered as covalent solids [3]. In each layer of graphite, carbon atoms are connected by covalent bonds and form a hexagonal network with each other. That is, in each layer, six carbon atoms form a hexagon, and a graphite layer or plate is formed from their connection. There is a covalent bond between the atoms in this plane and a weak van der Waals force between the planes, for this reason the graphite layers slide easily on top of each other and some properties of graphite such as being soft are due to the existence of this weak force. Its special cubic crystal. In the diamond crystal network, each carbon atom has a tetrahedral covalent bond with its four adjacent atoms, and all the atoms of a diamond crystal are connected. provides a special, the most famous and widely used of which are nanotubes and especially carbon nanotubes [1] (CNT). A carbon nanotube is actually a graphite layer that is in the shape of a tube or cylinder. in this investigation, fullerene and nine different nanotubes as drug carriers of 8-Hydroxyquino line has been used, first of all the drug molecule structure 8-HQ and nanotube drawn by nanotube modeler and Gauss view softwares then calculated by Gasussian09 with DFT/B3LYP-31G* method after these levels molecule 8-HQ from 2 sides of hetero atomic, nitrogen and a group of Hydroxyl put on different nano levels and calculated with below methods. the results was include energy connection information such as dipolar, atomic charges, angles and length bonds, basic attributes (potential ionzation, electron collective, chemical potential, hardness, softness) and in energy gaps in HOMO-LUMO, has been analysis and below results collected:

    from point of view connection energy and attract amount, nanotube CNT(9.0) is best interactive with drug molecules 8-HQ from nitrogen atom and from dipolar point of view nanotube BNNTdopedGe have most dipolar 8-HQ molecules, structure of this nanotube with 8-HQ molecules (especially from N atom) have shown acceptable pole and transport more charges rather other structures.

  • Contents & References of Theoretical study of 8-Hydroxyquinoline with fullerenes and carbon nanotubes as drug delivery nanocarriers

    List:

    Title

    Chapter One: Nanotechnology. 1

    1-1) Introduction. 2

    1-2) History of nanotechnology. 2

    1-3) transformations of carbon. 3

    1-3-1) Graphite: 3

    1-3-2) Diamond: 4

    1-3-3) Carbon nanotube (CNT): 4

    1-3-4) Fullerenes: 5

    1-4) Nanotubes 5

    1-4-1) Types of single-walled nanotubes 6

    1-4-1-1) Chair-type carbon nanotube. 6

    1-4-1-2) zigzag carbon nanotube. 7

    1-4-1-3) chiral or asymmetric nanotube. 7

    1-5) Physical and chemical properties of nanotubes 8

    1-6) Synthesis methods of carbon nanotubes. 9

    1-6-1) Electric arc method. 9

    1-6-2) Laser evaporation method. 10

    1-6-3) Chemical vapor deposition (CVD) 10

    1-7) Application of nanotubes 11

    1-7-1) Application of nanotubes in medicine (drug delivery) 11

    1-7-2) Application of nanotubes in cancer diagnosis and treatment. 12

    1-7-3) Application of nanotubes in composites 12

    1-7-4) Application of nanotubes in electronics. 13

    1-7-5) Application of nanotubes in the construction industry. 14

    1-8) fullerenes 14

    1-9) properties of fullerenes 15

    1-10) application of fullerenes 16

    1-10-1) application of photonics. 17

    1-10-2) reinforcing composites 17

    1-10-3) drug delivery. 17

    1-11) Production methods of fullerenes 17

    1-12) 8-Hydroxyquinoline. 18

    1-12-1) Medical application. 18

    1-12-2) Application of 8-HQ in agriculture. 19

    1-12-3) Application of 8-HQ in polymer engineering industry. 19

    Chapter Two: Computational Chemistry. 20

    2-1) Introduction. 21

    2-2) Informatics Chemistry. 21

    2-3) molecular mechanics. 22

    2-4) Electronic structure methods. 23

    2-4-1) Semi-empirical methods 23

    2-4-2) Initial methods. 24

    2-5) Gusin. 24

    2-6) Gaussian calculation methods. 25

    2-6-1) Harter Fack self-consistent field method (HF) 25

    2-6-2) Density functional theory (DFT) 27

    2-6-3) basis sets. 28

    2-7) Nuclear Independent Chemical Shift (NICS) 31

    2-8) Analysis of Natural Bond Orbital (NBO) 33

    2-9) HOMO and LUMO. 33

    2-10) Polarizability - hardness and softness. 35

    2-11) Comparison and interpretation of atomic charge calculations. 36

    Chapter three: working method and calculations. 37

    3-1) Work method 38

    3-2) Connection energy. 54

    3-3) Atomic charges. 55

    3-4) Dipole moment. 59

    3-5) Link length. 61

    3-6) angle calculations. 63

    3-7) fundamental properties. 66

    3-7-1) checking the values ??of ionization energy (I) 67

    3-7-2) checking the values ??of electron demand (A) 68

    3-7-3) checking the values ??of chemical potential ( ) 68

    3-7-4) checking the values ??of hardness (?) and softness (?) 68

    3-8) the gap between HOMO and LUMO 69

    Discussion and conclusion. 93

    Sources: 94

    Source:

    [1] Shokofar, Momeni, An Introduction to Nanotechnology, Shapan Publishing Center, Chapowell 1384

    [2] Iijima, S., Helical Microtubes of Graphite Carbon, Nature, 1991, 354, 8-56.                         [3] Mildred, D., Gene, D., Peter, E., Richiro, S., Carbon Nanotubes, Physics World., 1998, 1.            [4] Besley, J., Titman, and Wright, D., Theoretical Study of the 13C NMR Spectroscopy of Single-Wall Carbon Nanotubes., Am.Chem.soc.,2005,127,17948-17953.       

    [5] Ji,S.,Liu,C.,Zhang,B.,Yang,F.,Xu,J.,Long,J.,Fu,D.,Jin,C.,Ni,Q.,Yu,X.,Biochemica et

         Biophysica Acta.,2010,1806 

    [6] Iijima,S., Carbon Nanotubes: Past, Present, and Future, Phys B Condens Matter.,2002,

          323,1-5    

    [7] Collins, Ph.G., Zettl, A., Unique Characteristics of Cold Cathode Carbon Nanotube Matrix       Field Emitters, Phys.Rev., 1997, 9391-9399.  

    [8] Ebbesen, T.W., Ajayan, P.M., Large-Scale Synthesis of Carbon Nanotubes. Nature. ,1992,

          358,(6383)

    [9] Guo.T.,Nikoeve,P.,Rinzler,A.G.,Tomanek,D.,Colbert.D.T.,Smalley,R.E.,Self-Assembly

          Of,Self-Assembly

    Of Tubular Fullerenes.,J.Phys,Chem.,1995,99,(27),10694-10697.

    [10] Guo, T., Nikolaev, P., Thess, A., Colbert, D., Smalley, R., Catalytic growth of Single-Walled Nanotubes by Laser

    Vaporization.,Chem,Phys,Lett.,1995,243,49-54.

    [11] Beckman,W.,UC Researchers Shatter World Records with Length of Carbon Nanotube

    Arrays.,University of Cincinnati.,2007,4,27

    [12] Inami,N.,Ambri Mohamed, M., Shikoh, E., Fujiwara, A., Synthesis-Condition Dependence of

    Carbon Nanotube growth by Alcohol Catalytic ChemicalVapor Deposition Method.,sic,

             Technol.Adv.Matter.,2007,8(4),292.

    [13] Ishigami, N., Ago, H., Imamoto, K., Tsuji, M. ., Lakoubovski, K ., Minami, N ., Crystal Plane Dependent Growth of Aligned Single Walled Nanotubes on Sapphire., J.Am.Chem.Soc., 2008,130(30),9918-9924.  

    Research., 2006, 23, 7. 

    [16] Choi, Y.E., Kwak, J.W., Park, J.W., Nanotechnology for Early Cancer Detection, Sensors.,

           2010,10, 428-455.

    [17] Sithahara,B.,Shi,X.,Walbomers,X.F.,Lio,H.,Cuijpers,V.,Wilson,L.J.,Mikos,A.G.,Janson,

    J.A., In Vivo Biocompatibility of Ultra-Short Single Walled Carbon Nanotube, Bone. ,

            2008,43,2,362-370.

    [18] Dalton,A.,Nanotubes May Heal Broken Bones.Wired Com.,2005

    [19] Peterson,E.J.,Tu,X.,Dizdaroglu,M.,Zheng,M.,Nelson,B.C., Protective Roles of Single –

    Wall Carbon Nanotubes in Ultrasonication-Induced DNA Base Damage, Small., 2013, 9, 2

    and Electrical Conductivity, J Mater Chem.,2012,22,903-908. [21] Meyyappan, M., Carbon Nanotubes Science and Application (1st ed)., CRC Press LLC., 2005. [22] Cao, Q., Kim, N., Pimparker, J.P., Kulkami, C., Wang, M., Shim, K., Roy, M.A., Rojers, J. A.,

    Medium-Scale Carbon Nanotube Thin - Film Integrated Circuits on Flexible Plastic

    Substrates, Nature., 2008, 454, 495.

    [23] Holister, P., Roman, C., Harper, T., Fullerenes Nanoparticles, Scientifica Technology White

    Papers., 2003.

    [24] Hirsch, A., Brettreich, M., Fullerenes: Chemistry and Reactions, Willey VCH Verlag

           GMBH., 2005.

    [25] Panina, L.K., Kurochkin, V.E., Bogomolova, E.V., Evstrapov, A.A., Spitsina, N.G., Doklady

            Biological Science.,1997,357-530.

    [26] Sigma, A., 8-Hydroxyquinoline, Retrieved.,2012,5,23.

    [27] Shen, A.Y., Wu, S.N., Chiu, C.T., Synthesis and Sitoxicity Evaluation of some 8-Hydroxy Quinoline Derivatives, Journal of Pharmacy and Pharmacology, 1999, 51, 5, 543-548.       

    [28] Katakura, R., Koid, Y., Configuration-Specific Synthesis of the Fcial and Meridional Isomers, Inorganic Chemistry., 2006, 45, 15, 5730-5732.                                                       

    Effect of 8-Hydroxyquinoline Citrate and Silver Thiosulfate on Lifespan and Amount

             Chlorophyll of cut flowers of Drobtar cultivar, 5th National Conference of New Ideas in Agriculture, Khorasan, Asla May Azad University

            Khorasan, 1389.

Theoretical study of 8-Hydroxyquinoline with fullerenes and carbon nanotubes as drug delivery nanocarriers