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Research Articles

Detailed Quantum Mechanical Studies on Three Bioactive Benzimidazole Derivatives and Their Raman Enhancement on Adsorption over Graphene Sheets

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Pages 2581-2590 | Received 09 Mar 2020, Accepted 18 Oct 2020, Published online: 24 Nov 2020

References

  • Milan Nobilis, Thomas Jira, Miroslav Lísa, Michal Holčapek, Barbora Szotáková, Jiří Lamka, and Lenka Skálová, “A Chiral and Chiral High-Performance Liquid Chromatographic Determination of Flubendazole and Its Metabolites in Biomatrices Using UV Photodiode-Array and Mass Spectrometric Detection,” Journal of Chromatography A 1149, no. 1 (2007): 112–20.
  • X. Zhou, J. Liu, J. Zhang, Y. Wei, and H. Li, “Flubendazole Inhibits Glioma Proliferation by G2/M Cell Cycle Arrest and Pro-Apoptosis,” Cell Death Discovery 4, (2018): 18.
  • Martin Michaelis, Bishr Agha, Florian Rothweiler, Nadine Löschmann, Yvonne Voges, Michel Mittelbronn, Tatjana Starzetz, Patrick N. Harter, Behnaz A. Abhari, Simone Fulda, et al. “Identification of Flubendazole as Potential Anti-neuroblastoma Compound in a Large Cell Line Screen,” Scientific Reports 5, (2015): 8202–10.
  • Santosh Chauhan, Zahra Ahmed, Steven B. Bradfute, John Arko-Mensah, Michael A. Mandell, Seong Won Choi, Tomonori Kimura, Fabien Blanchet, Anna Waller, Michal H. Mudd, et al. “Pharmaceutical Screen Identifies Novel Target Processes for Activation of Autophagy with a Broad Translational Potential,” Nature Communications 6, (2015): 8620.
  • Karem Čáňová, L. Rozkydalová, Doris Vokurková, and Emil Rudolf, “Flubendazole Induces Mitotic Catastrophe and Apoptosis in Melanoma Cells,” Toxicology in Vitro 46, (2018): 313–22.
  • Haruo Yoshimura, “Effect of Oral Dosing Vehicles on the Developmental Toxicity of Flubendazole in Rats,” Reproductive Toxicology 17, no. 4 (2003): 377–85.
  • V. Ragupathi, A. Stephen, D. Arivoli, and S. Kumaresan, “Pass-Assisted Preidiction of Biological Activity Spectra of Methanolic Extract of Gymnopilus Junonius, a Wild Mushroom from Southern Western Ghats India,” European Journal of Pharmaceutical and Medical Research 5, (2018): 340–7.
  • C. Yohannan Panicker, Hema Tresa Varghese, L. Ushakumari, Y. Sheena Mary, Jyotirmoy Sarkar, and Joydeep Chowdhury, “Concentration and pH Dependent SERS Spectra of Sulfanilic Acid Sodium Salt on Colloidal Silver Particles,” Journal of Raman Spectroscopy 41, no. 9 (2010): 944–51.
  • Y. Sheena Mary, C. Yohannan Panicker, C. N. Kavitha, H. S. Yathirajan, M. S. Siddegowda, Sandra M. A. Cruz, Helena I. S. Nogueira, Abdulaziz A. Al-Saadi, Christian Van Alsenoy, and Javeed Ahmad War, “Spectroscopic Investigation (FT-IR, FT-Raman and SERS), Vibrational Assignments, HOMO-LUMO Analysis and Molecular Docking Study of Opipramol,” Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy 137, (2015): 547–59.
  • Aljawhar H. Almuqrin, Jamelah S. Al-Otaibi, Y. Sheena Mary, and Shyma Y. Mary, “DFT Computational Study towards Investigating Psychotropic Drugs, Promazine and Trifluoperazine Adsorption on Graphene, Fullerene and Carbon Cyclic Ring Nanoclusters,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 246, (2021): 119012.
  • Jamelah S. Al-Otaibi, Aljawhara H. Almuqrin, Y. Sheena Mary, Shyma Y. Mary, and Renjith Thomas, “Modeling the Conformational Preference, Spectral Analysis and Other Quantum Mechanical Studies on Three Bioactive Aminobenzoate Derivatives and Their SERS Active Graphene Complexes,” Polycyclic Aromatic Compounds (2020). https://doi.org/https://doi.org/10.1080/10406638.2020.1827270
  • Jamelah S. Al-Otaibi, Aljawhara H. Almuqrin, Y. Sheena Mary, Shyma Y. Mary, and Christian Van Alsenoy, “DFT and Molecular Docking Studies of Self-Assembly of Sulfone Analogues and Graphene,” Journal of Molecular Modeling 26, no. 10 (2020): 273.
  • Aljawhara H. Almuqrin, Jamelah S. Al-Otaibi, Y. Sheena Mary, Renjith Thomas, Savaş Kaya, and Dilara Özbakır Işın, “Spectral Analysis and Detailed Quantum Mechanical Investigation of Some Acetanilide Analogues and Their Self-assemblies with Graphene and Fullerene,” Journal of Molecular Modeling 26, no. 9 (2020): 254.
  • Y. Sheena Mary, and Shyma Y. Mary, “Utilization of Doped/undoped Graphene Quantum Dots for Ultrasensitive Detection of Duphaston, a SERS Platform,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 244, (2021): 118865.
  • Jamelah S. Al-Otaibi, Y. Sheena Mary, Shyma Y. Mary, Savaş Kaya, and Sulta Erkan, “Spectral Analysis and DFT Investigation of Some Benzopyran Analogues and Their Self Assemblies with Graphene,” Journal of Molecular Liquids 317, (2020): 113924.
  • Jamelah S. Al-Otaibi, Y. Sheena Mary, Renjith Thomas, and Savaş Kaya, “Detailed Electronic Structure, Physico-Chemical Properties, Excited State Properties, Virtual Bioactivity Screening and SERS Analysis of Three Guanine Based Antiviral Drugs, Valacyclovir HCl Hydrate, Acyclovir and Ganciclovir,” Polycyclic Aromatic Compounds (2020). https://doi.org/https://doi.org/10.1080/10406638.2020.1773876
  • Aljawhara H. Almuqrin, Jamelah Al-Otaibi, Y. Sheena Mary, Shyma Y. Mary, and Renjith Thomas, “Structural Study of Letrozole and Metronidazole and Formation of Self Assembly with Graphene and Fullerene with the Enhancement of Physical, Chemical and Biological Activities,” Journal of Biomolecular Structure and Dynamics (2020). https://doi.org/https://doi.org/10.1080/07391102.2020.179420
  • Jamelah Al-Otaibi, Aljawhara H. Almuqrin, Y. Sheena Mary, and Shyma Y. Mary, “Comprehensive Quantum Mechanical Studies on Three Bioactive Anastrozole Based Triazole Analogues and Their SERS Active Graphene Complex,” Journal of Molecular Structure 1217, (2020): 128388.
  • Yu Jiang, J. Wang, Luca Malfatti, Davide Carboni, Nina Senes, and Plinio Innocenzi, “Highly Durable Graphene-Mediated Surface Enhanced Raman Scattering (G-SERS) Nanocomposites for Molecular Detection,” Applied Surface Science 450, (2018): 451–60.
  • Reza Samiee, Bahram Ramezanzadeh, Mohammad Mahdavian, Eiman Alibakhshi, and Ghasem Bahlakeh, “Graphene Oxide Nano-Sheets Loading with Praseodymium Cations: Adsorption-Desorption Study, Quantum Mechanics Calculations and Dual Active-Barrier Effect for Smart Coatings Fabrication,” Journal of Industrial and Engineering Chemistry 78, (2019): 143–54. https://doi.org/https://doi.org/10.1016/j.jiec.2019.06.024
  • Samaneh Saadatmandi, Bahram Ramezanzadeh, Morteza Asghari, and Ghasem Bahlakeh, “Graphene Oxide Nanoplatform Surface Decoration by Spherical Zinc-Polypyrrole Nanoparticles for Epoxy Coating Properties Enhancement: Detailed Explorations from Integrated Experimental and Electronic-Scale Quantum Mechanics Approaches,” Journal of Alloys and Compounds 816, (2020): 152510.
  • Mohammad Ramezanzadeh, Bahram Ramezanzadeh, Mohammad Mahdavian, and Ghasem Bahlakeh, “Development of Metal-Organic Framework (MOF) Decorated Graphene Oxide Nanoplatforms for Anti-Corrosion Epoxy Coatings,” Carbon 161, (2020): 231–51.
  • Mohammad Ramezanzadeh, Morteza Asghari, Bahram Ramezanzadeh, and Ghasem Bahlakeh, “Fabrication of an Efficient System for Zn Ions Removal from Industrial Waste Water Based on Graphene Oxide Nanosheets Decorated with Highly Crystalline Polyaniline Nanofibers (GO-PANI): Experimental and ab Initio Quantum Mechanics Approach,” Chemical Engineering Journal 337, (2018): 385–97.
  • Rooshanak Miraftab, Behzad Karimi, Ghasem Bahlakeh, and Bahram Ramezanzadeh, “Complementary Experimental and Quantum Mechanics Approaches for Exploring the Mechanical Characteristics of Epoxy Composites Loaded with Grphene Oxide-Polyaniline Nanofibers,” Journal of Industrial and Engineering Chemistry 53, (2017): 348–59.
  • Bahram Ramezanzadeh, Ghasem Bahlakeh, M. H. Mohamadzadeh Moghadam, and Rooshanak Miraftab, “Impact of Size Controlled p-Phenylenediamine (PPDA)-Functionalized Graphene Oxide Nanosheets on the GO-PPDA/Epoxy anti-Corrosion, Interfacial Interactions and Mechanical Properties Enhancement: Experimental and Quantum Mechanics Investigations,” Chemical Engineering Journal 335, (2018): 737–55.
  • Sajjad Akbarzadeh, Mohammad Ramezanzadeh, Bahram Ramezanzadeh, and Ghasem Bahlakeh, “A Green Assisted Route for the Fabrication of a High-efficiency Self-healing Anti-corrosion Coating Through Graphene Oxide Nanoplatform Reduction by Tamarindus Indica Extract,” Journal of Hazardous Materials 390, (2020): 122147.
  • Bahram Ramezanzadeh, Pooneh Kardar, Ghasem Bahlakeh, Yasmin Hayatgheib, and Mohammad Mahdavian, “Fabrication of a Highly Tunable Graphene Oxide Composite through Layer-by-Layer Assembly of Highly Crystalline Polyaniline Nanofibers and Green Corrosion Inhibitors: Complementary Experimental and First-Principles Quantum Mechanics Modeling Approaches,” The Journal of Physical Chemistry C 121, no. 37 (2017): 20433–50.
  • Mojtaba Kasaeian, Ebrahim Ghasemi, Bahram Ramezanzadeh, Mohammad Mahdavian, and Ghasem Bahlakeh, “Construction of a Highly Effective Self-Repair Corrosion-Resistant Epoxy Composite through Impregnation of 1H-Benzimidazole Corrosion Inhibitor Modified Graphene Oxide Nanosheets (GO-BIM),” Corrosion Science 145, (2018): 119–34.
  • Petr Lazar, František Karlický, Petr Jurečka, Mikuláš Kocman, Eva Otyepková, Klára Šafářová, and Michal Otyepka, “Adsorption of Small Organic Molecules on Graphene,” Journal of the American Chemical Society 135, no. 16 (2013): 6372–7.
  • Jamelah S. Al-Otaibi, Aljawhara H. Almuqrin, Y. Sheena Mary, and Renjith Thomas, “Modeling the Conformational Preference, Spectroscopic Properties, UV Light Harvesting Efficiency, Biological Receptor Inhibitory Ability and Other Physic-Chemical Properties of Five Imidazole Derivatives Using Quantum Mechanical and Molecular Mechanics Tools,” Journal of Molecular Liquids 310, (2020): 112871.
  • M. Smitha, Y. Sheena Mary, Mossaraf Hossain, K. S. Resmi, Stevan Armakovic, Sanja J. Armakovic, Rani Pavithran, Ashis Kumar Nanda, and Christian Van Alsenoy, “Two Novel Imidazole Derivatives - Combined Experimental and Computational Study,” Journal of Molecular Structure 1173, (2018): 221–39.
  • P. Krishna Murthy, M. Smitha, Y. Sheena Mary, Stevan Armakovic, Sanja J. Armakovic, R. Sreenivasa Rao, P. A. Suchetan, L. Giri, Rani Pavithran, and Christian Van Alsenoy, “Supramolecular Architecture of 5-Bromo-7-Methoxy-1-Methyl-1H-Benzoimidazole.3H2O: Synthesis, Spectroscopic Investigations, DFT Computation, MD Simulations and Docking Studies,” Journal of Molecular Structure 1149, (2017): 602–12.
  • K. B. Benzon, Y. Sheena Mary, Hema Tresa Varghese, C. Yohannan Panicker, Stevan Armakovic, Sanja J. Armakovic, Kiran Pradhan, Ashis Kumar Nanda, and Christian Van Alsenoy, “Spectroscopic, DFT, Molecular Dynamics and Molecular Docking Study of 1-Butyl-2-(4-Hydroxyphenyl)-4,5-Dimethyl-Imidazole 3-Oxide,” Journal of Molecular Structure 1134, (2017): 330–44.
  • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G.E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, et al. Gaussian 09, Revision B.01 (Wallingford, CT: Gaussian, Inc., 2010).
  • Bio-Rad Laboratories, Inc. “Spectra Base,” http://spectrabase.com/ (June 24,2018).
  • Jeng-Da Chai, and Martin Head-Gordon, “Long-Range Corrected Hybrid Density Functionals with Damped Atom-Atom Dispersion Corrections,” Physical Chemistry Chemical Physics 10, no. 44 (2008): 6615–20.
  • E. D. Glendening, A. E. Reed, J. E. Carpenter, F. Weinhold, NBO (Pittsburgh, PA: Gaussian Inc., 2003).
  • Bhaskaran Sureshkumar, Y. Sheena Mary, C. Yohannan Panicker, Somasekharan Suma, Stevan Armakovic, Sanja J. Armakovic, Christian Van Alsenoy, and Badiadka Narayana, “Quinoline Derivatives as Possible Lead Compounds for anti-Malarial Drugs: Spectroscopic, DFT and MD Study,” Arabian Journal of Chemistry 13, no. 1 (2020): 632–48.
  • Mossaraf Hossain, Renjith Thomas, Y. Sheena Mary, K. S. Resmi, Stevan Armakovic, Sanja J. Aramkovic, Ashis Kumar Nanda, G. Vijayakumar, and Christian Van Alsenoy, “Understanding Reactivity of Two Newly Synthetized Imidazole Derivatives by Spectroscopic Characterization and Computational Study,” Journal of Molecular Structure 1158, (2018): 176–96.
  • Y. Sheena Mary, Hema Tresa Varghese, C. Yohannan Panicker, M. Girisha, Belakavadi K. Sagar, Hemmige S. Yathirajan, Abdulaziz A. Al-Saadi, and Christian Van Alsenoy, “Vibrational Spectra, HOMO, LUMO, NBO, MEP Analysis and Molecular Docking Study of 2,2-diphenyl-4-(Piperidin-1-yl)butanamide,” Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy 150, (2015): 543–56.
  • Parvaneh Shafieyoon, Ebrahim Mehdipour, and Y. Sheena Mary, “Synthesis, Characterization and Biological Investigation of Glycine Based Sulfonamide Derivative and Its Complex: Vibration Assignment, HOMO-LUMO Analysis, MEP and Molecular Docking,” Journal of Molecular Structure 1181, (2019): 244–52.
  • Veena S. Kumar, Y. Sheena Mary, Kiran Pradhan, Dhiraj Brahman, Y. Shyma Mary, Renjith Thomas, M. S. Roxy, and C. Van Alsenoy, “Synthesis, Spectral Properties, Chemical Descriptors and Light Harvesting Studies of a New Bioactive Azo Imidazole Compound,” Journal of Molecular Structure. 1199, (2020): 127035.
  • Ting Zhang, Xuehong Wei, Ying Zuo, and Jianbin Chao, “An Efficient Measure to Improve the NLO Performance by Point Charge Electric Field,” Optik 182, (2019): 295–302.
  • C. Yohannan Panicker, Hema Tresa Varghese, K. C. Mariamma, Koshy John, Samuel Mathew, Jarmila Vinsova, Christian Van Alsenoy, and Y. Sheena Mary, “Spectroscopic Investigations and Computational Study of 2-[Acetyl(4-Bromophenyl)Carbamoyl]-4-Chlorophenyl Acetate,” Journal of Raman Spectroscopy 41, no. 6 (2010): 707–16.
  • Y. Sheena Mary, Pankaj B. Miniyar, Y. Shyma Mary, K. S. Resmi, C. Yohannan Panicker, Stevan Armaković, Sanja J. Armaković, Renjith Thomas, and B. Sureshkumar, “Synthesis and Spectroscopic Study of Three New Oxadiazole Derivatives with Detailed Computational Evaluation of Their Reactivity and Pharmaceutical Potential,” Journal of Molecular Structure 1173, (2018): 469–80.
  • Y. Sheena Mary, C. Yohannan Panicker, M. Sapnakumari, B. Narayana, B. K. Sarojini, Abdulaziz A. Al-Saadi, Christian Van Alsenoy, Javeed Ahmad War, and H. K. Fun, “Molecular Structure, FT-IR, Vibrational Assignments, HOMO-LUMO Analysis and Molecular Docking Study of 1-[5-(4-Bromophenyl)-3-(4-Fluorophenyl)-4,5-Dihydro-1H-Pyrazol-1-yl]Ethanone,” Spectrochimica Acta 136, (2015): 473–82.
  • Y. Sheena Mary, C. Yohannan Panicker, M. Sapnakumari, B. Narayana, B. K. Sarojini, Abdulaziz A. Al-Saadi, Christian Van Alsenoy, and Javeed Ahmad War, “FT-IR, NBO, HOMO-LUMO, MEP Analysis and Molecular Docking Study of 1-[3-(4-Fluorophenyl)-5-Phenyl-4,5-Dihydro-1H-Pyrazol-1yl]Ethanone,” Spectrochimica Acta 136, (2015): 483–93.
  • Renjith Thomas, Mossaraf Hossain, Y. Sheena Mary, K. S. Resmi, Stevan Armaković, Sanja J. Armaković, Ashis Kumar Nanda, Vivek Kumar Ranjan, G. Vijayakumar, and C. Van Alsenoy, “Spectroscopic Analysis and Molecular Docking Studies of Imidazole Derivatives and Investigation of Its Reactive Properties by DFT and Molecular Dynamics Simulations,” Journal of Molecular Structure 1158, (2018): 156–75. https://doi.org/https://doi.org/10.1016/j.molstruc.2018.01.021
  • Noel P. G. Roeges, A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures (New York, NY: John Wiley and Sons Inc., 1994).
  • M. Fleischmann, P. J. Hendra, and A. J. McQuillan, “Raman Spectra of Pyridine Adsorbed at a Silver Electrode,” Chemical Physics Letters 26, no. 2 (1974): 163–6.
  • M. Grant Albrecht, and J. Alan Creighton, “Anomalously Intense Raman Spectra of Pyridine at a Silver Electrode,” Journal of the American Chemical Society 99, no. 15 (1977): 5215–7.
  • David L. Jeanmaire, and Richard P. Van Duyne, “Surface Raman Spectroelectrochemistry: Part I > Heterocyclic, Aromatic, and Aliphatic Amines Adsorbed on the Anodized Silver Electrode,” Journal of Electroanalytical Chemistry and Interfacial Electrochemistry 84, no. 1 (1977): 1–20.
  • E. Smith, G. Dent, “Modern Raman Spectroscopy – A Practical Approach,” 2005,
  • Katrin Kneipp, Yang Wang, Harald Kneipp, Lev T. Perelman, Irving Itzkan, Ramachandra R. Dasari, and Michael S. Feld, “Single Molecule Detection Using Surface Enhanced Raman Scattering (SERS),”Physical Review Letters 78, no. 9 (1997): 1667–70.
  • Shuming Nie, and Steven R. Emory, “Probing Single Molecules and Single Nano Particles by Surface Enhanced Raman Scattering,” Science 275, no. 5303 (1997): 1102–6.
  • K. S. Novoselov, A. K. Geim, S. V. Morozov, D. Jiang, Y. Zhang, S. V. Dubonos, I. V. Grigorieva, and A. A. Firsov, “Electric Field in Atomically Thin Carbon Films,” Science 306, no. 5696 (2004): 666–9.
  • Vaishali Sharma, Narayan N. Som, Sharad Babu Pillai, and Prafulla K. Jha, “Utilization of Doped GQDs for Ultrasensitive Detection of Catastrophic Melamine: A New SERS Platform,” Spectrochimica Acta Part A Molecular and Biomolecular Spectroscopy 224, (2020): 117352.
  • Alexey Lagunin, Alla Stepanchikova, Dmitrii Filimonov, and Vladimir Poroikov, “PASS: Prediction of Activity Spectra for Biologically Active Substances,” Bioinformatics 16, no. 8 (2000): 747–8.
  • D. Duhovny, R. Nussinov, H.J. Wolfson, “Efficient Unbound Docking of Rigid Molecules,” in Proceedings of the 2nd Workshop on Algorithms in Bioinformatics(WABI) Rome, Italy, Lecture Notes in Computer Science 2452, edited by Gusfield (Berlin, Germany: Springer Verlag, 2002), 185–200.
  • C. Zhang, G. Vasmatzis, J. L. Cornette, and C. DeLisi, “Determination of Atomic Desolvation Energies from the Structures of Crystallized Proteins,” Journal of Molecular Biology 267, no. 3 (1997): 707–26.
  • Rong Chen, Julian Mintseris, Joël Janin, and Zhiping Weng, “A protein-protein docking benchmark,” Proteins 52, no. 1 (2003): 88–91.
  • M. L. Connolly, “Analytical Molecular Surface Calculation,” Journal of Applied Crystallography 16, no. 5 (1983): 548–58.
  • Mam Y. Mboge, Brian P. Mahon, Robert McKenna, and Susan C. Frost, “Carbonic Anhydrases: Role in pH Control and Cancer,” Metabolites 8, no. 1 (2018): 19.

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