Combinatorial Effect of Syringic Acid-Pyrazinamide Adduct against Luminal Type Breast Cancer Investigated through DFT, Drug-Likeness, and Molecular Docking Simulation

References

• N. K. Duggirala, M. L. Perry, O. Almarsson, and M. J. Zaworotko, “Pharmaceutical Cocrystals: Along the Path to Improved Medicines,” Chemical Communications 52 (2016): 640–55.
   PubMed Web of Science ®Google Scholar
• G. Bolla, and A. Nangia, “Pharmaceutical Cocrystals: Walking the Talk,” Chemical Communications 52 (2016): 8342–60.
   PubMed Web of Science ®Google Scholar
• C. A. Gunawardana, and C. B. Aakeröy, “Co-Crystal Synthesis: Fact, Fancy, and Great Expectations,” Chemical Communications (Cambridge, England) 54, no. 100 (2018): 14047–60. doi:10.1039/c8cc08135b
   PubMed Web of Science ®Google Scholar
• J. R. Wang, Q. Yu, W. Dai, and X. Mei, “Drug–Drug co-Crystallization Presents a New Opportunity for the Development of Stable Vitamins,” Chemical Communications (Cambridge, England) 52, no. 17 (2016): 3572–5. doi:10.1039/c5cc10297a
   PubMed Web of Science ®Google Scholar
• T. M. Viswanathan, K. Chitradevi, A. Zochedh, R. Vijayabhaskar, S. Sukumaran, S. Kunjiappan, N. S. Kumar, K. Sundar, E. Babkiewicz, P. Maszczyk, et al, “Guanidine–Curcumin Complex-Loaded Amine-Functionalised Hollow Mesoporous Silica Nanoparticles for Breast Cancer Therapy,” Cancers 14, no. 14 (2022): 3490. doi:10.3390/cancers14143490
   PubMed Web of Science ®Google Scholar
• B. Laddomada, S. Caretto, and G. Mita, “Wheat Bran Phenolic Acids: Bioavailability and Stability in Whole Wheat-Based Foods,” Molecules (Basel, Switzerland) 20, no. 9 (2015): 15666–85. doi:10.3390/molecules200915666
   PubMed Web of Science ®Google Scholar
• L. F. Călinoiu, and D. C. Vodnar, “Whole Grains and Phenolic Acids: A Review on Bioactivity, Functionality, Health Benefits and Bioavailability,” Nutrients 10, no. 11 (2018): 1615. doi:10.3390/nu10111615
   PubMed Web of Science ®Google Scholar
• S. Chandra, and E. Gonzalez de Mejia, “Polyphenolic Compounds, Antioxidant Capacity, and Quinone Reductase Activity of an Aqueous Extract of Ardisia Compressa in Comparison to Mate (Ilex Paraguariensis) and Green (Camellia Sinensis) Teas,” Journal of Agricultural and Food Chemistry 52, no. 11 (2004): 3583–9. doi:10.1021/jf0352632
   PubMed Web of Science ®Google Scholar
• V. Lattanzio, “Bioactive Polyphenols: Their Role in Quality and Storability of Fruit and Vegetables,” Journal of Applied Botany 77, no. 5/6 (2003): 128–46.
   Google Scholar
• A. Somoskovi, M. M. Wade, Z. Sun, and Y. Zhang, “Iron Enhances the Antituberculous Activity of Pyrazinamide,” The Journal of Antimicrobial Chemotherapy 53, no. 2 (2004): 192–6. doi:10.1093/jac/dkh042
   PubMed Web of Science ®Google Scholar
• P. Santucci, D. J. Greenwood, A. Fearns, K. Chen, H. Jiang, and M. G. Gutierrez, “Intracellular Localisation of Mycobacterium tuberculosis Affects Efficacy of the Antibiotic Pyrazinamide,” Nature Communications 12, no. 1 (2021): 1–15. doi:10.1038/s41467-021-24127-3
   PubMed Web of Science ®Google Scholar
• M. Dolezal, L. Palek, J. Vinsova, V. Buchta, J. Jampilek, and K. Kralova, “Substituted Pyrazinecarboxamides: Synthesis and Biological Evaluation,” Molecules (Basel, Switzerland) 11, no. 4 (2006): 242–56. doi:10.3390/11040242
   PubMed Web of Science ®Google Scholar
• R. Thipparaboina, S. Mittapalli, S. Thatikonda, A. Nangia, V. G. M. Naidu, and N. R. Shastri, “Syringic Acid: Structural Elucidation and co-Crystallization,” Crystal Growth & Design 16, no. 8 (2016): 4679–87. doi:10.1021/acs.cgd.6b00750
   Web of Science ®Google Scholar
• F. Liu, F. B. Jiang, Y. T. Li, R. M. Liu, Z. Y. Wu, and C. W. Yan, “Cocrystallization with Syringic Acid Presents a New Opportunity for Effectively Reducing the Hepatotoxicity of Isoniazid,” Drug Development and Industrial Pharmacy 46, no. 6 (2020): 988–95. doi:10.1080/03639045.2020.1764024
   PubMed Web of Science ®Google Scholar
• M. Reggane, J. Wiest, M. Saedtler, C. Harlacher, M. Gutmann, S. H. Zottnick, P. Piechon, I. Dix, K. Müller-Buschbaum, U. Holzgrabe, et al, “Bioinspired co-Crystals of Imatinib Providing Enhanced Kinetic Solubility,” European Journal of Pharmaceutics and Biopharmaceutics 128 (2018): 290–9. doi:10.1016/j.ejpb.2018.05.012
   PubMed Web of Science ®Google Scholar
• Y. M. Yu, M. C. Yu, L. Y. Wang, Y. T. Li, Z. Y. Wu, and C. W. Yan, “A Supramolecular Adduct of Tegafur and Syringic Acid: The First Tegafur-Nutraceutical Cocrystal with Perfected in Vitro and in Vivo Characteristics as Well as Synergized Anticancer Activities,” New Journal of Chemistry 44, no. 37 (2020): 15994–6005. doi:10.1039/D0NJ03033C
   Web of Science ®Google Scholar
• C. J. Jiang, Y. F. Xia, and Y. S. Xie, “The Crystal Structure of the Cocrystal 4-Hydroxy-3, 5-Dimethoxybenzoic Acid–Pyrazine-2-Carboxamide (1/1), C14H15N3O6,” Zeitschrift Für Kristallographie - New Crystal Structures 237, no. 5 (2022): 845–7. doi:10.1515/ncrs-2022-0288
   Web of Science ®Google Scholar
• H. S. Kim, I. Park, H. J. Cho, G. Gwak, K. Yang, B. N. Bae, K. W. Kim, S. Han, H. J. Kim, and Y. D. Kim, “Analysis of the Potent Prognostic Factors in Luminal-Type Breast Cancer,” Journal of Breast Cancer 15, no. 4 (2012): 401–6. doi:10.4048/jbc.2012.15.4.401
   PubMed Web of Science ®Google Scholar
• S. M. Hiremath, A. S. Patil, C. S. Hiremath, M. Basangouda, S. S. Khemalapure, N. R. Patil, S. B. Radder, S. J. Armaković, and S. Armaković, “Structural, Spectroscopic Characterization of 2-(5-Methyl-1-Benzofuran-3-yl) Acetic Acid in Monomer, Dimer and Identification of Specific Reactive, Drug Likeness Properties: Experimental and Computational Study,” Journal of Molecular Structure 1178 (2019): 1–17. doi:10.1016/j.molstruc.2018.10.007
   Web of Science ®Google Scholar
• G. Venkatesh, C. Kamal, P. Vennila, M. Govindaraju, Y. S. Mary, S. Armakovic, S. J. Armakovic, S. Kaya, and C. Y. Panicker, “Molecular Dynamic Simulations, ALIE Surface, Fukui Functions Geometrical, Molecular Docking and Vibrational Spectra Studies of Tetra Chloro p and m-Xylene,” Journal of Molecular Structure 1171 (2018): 253–67. doi:10.1016/j.molstruc.2018.06.001
   Web of Science ®Google Scholar
• Y. S. Mary, Y. S. Mary, S. Armaković, S. J. Armaković, R. Yadav, I. Celik, P. Mane, and B. Chakraborty, “Stability and Reactivity Study of Bio-Molecules Brucine and Colchicine towards Electrophile and Nucleophile Attacks: Insight from DFT and MD Simulations,” Journal of Molecular Liquids 335 (2021): 116192. doi:10.1016/j.molliq.2021.116192
   Web of Science ®Google Scholar
• M. Muthukkumar, T. Bhuvaneswari, G. Venkatesh, C. Kamal, P. Vennila, S. Armaković, S. J. Armaković, Y. Sheena Mary, and C. Yohannan Panicker, “Synthesis, Characterization and Computational Studies of Semicarbazide Derivative,” Journal of Molecular Liquids 272 (2018): 481–95. doi:10.1016/j.molliq.2018.09.123
   Web of Science ®Google Scholar
• M. J. Frisch, Gaussian 09, Revision C. 01 & B. 01 (Pittsburgh, PA: Gaussian Inc., 2010).
   Google Scholar
• S. Armaković, and S. J. Armaković, “Atomistica Online–Web Application for Generating Input Files for ORCA Molecular Modelling Package Made with the Anvil Platform,” Molecular Simulation 49, no. 1 (2023): 117–23. doi:10.1080/08927022.2022.2126865
   Web of Science ®Google Scholar
• T. Yanai, D. P. Tew, and N. C. Handy, “A New Hybrid Exchange–Correlation Functional Using the Coulomb-Attenuating Method (CAM-B3LYP),” Chemical Physics Letters 393, no. 1–3 (2004): 51–7. doi:10.1016/j.cplett.2004.06.011
   Web of Science ®Google Scholar
• C. S. Abraham, S. Muthu, J. C. Prasana, S. Armaković, S. J. Armaković, F. Rizwana, B. Geoffrey, and H. A. David R, “Computational Evaluation of the Reactivity and Pharmaceutical Potential of an Organic Amine: A DFT, Molecular Dynamics Simulations and Molecular Docking Approach,” Spectrochimica Acta Part A, Molecular and Biomolecular Spectroscopy 222 (2019): 117188. doi:10.1016/j.saa.2019.117188
   PubMed Web of Science ®Google Scholar
• S. Muthu, J. Uma Maheswari, and T. Sundius, “Quantum Mechanical, Spectroscopic Studies (FT-IR, FT-Raman, NMR, UV) and Normal Coordinates Analysis on 3-([2-(Diaminomethyleneamino) Thiazol-4-yl] Methylthio)-N′-Sulfamoylpropanimidamide,” Spectrochimica Acta Part A, Molecular and Biomolecular Spectroscopy 108 (2013): 307–18. doi:10.1016/j.saa.2013.02.022
   PubMed Web of Science ®Google Scholar
• E. I. Paulraj, and S. Muthu, “Spectroscopic Studies (FTIR, FT-Raman and UV), Potential Energy Surface Scan, Normal Coordinate Analysis and NBO Analysis of (2R, 3R, 4R, 5S)-1-(2-Hydroxyethyl)-2-(Hydroxymethyl) Piperidine-3, 4, 5-Triol by DFT Methods,” Spectrochimica Acta Part A, Molecular and Biomolecular Spectroscopy 108 (2013): 38–49. doi:10.1016/j.saa.2013.01.061
   PubMed Web of Science ®Google Scholar
• M. H. Rahuman, S. Muthu, B. R. Raajaraman, M. Raja, and H. Umamahesvari, “Investigations on 2-(4-Cyanophenylamino) Acetic Acid by FT-IR, FT-Raman, NMR and UV-Vis Spectroscopy, DFT (NBO, HOMO-LUMO, MEP and Fukui Function) and Molecular Docking Studies,” Heliyon 6, no. 9 (2020): e04976. doi:10.1016/j.heliyon.2020.e04976
   PubMed Web of Science ®Google Scholar
• S. Muthu, and A. Prabhakaran, “Vibrational Spectroscopic Study and NBO Analysis on Tranexamic Acid Using DFT Method,” Spectrochimica Acta Part A, Molecular and Biomolecular Spectroscopy 129 (2014): 184–92. doi:10.1016/j.saa.2014.03.050
   PubMed Web of Science ®Google Scholar
• O. Noureddine, S. Gatfaoui, S. A. Brandan, A. Sagaama, H. Marouani, and N. Issaoui, “Experimental and DFT Studies on the Molecular Structure, Spectroscopic Properties, and Molecular Docking of 4-Phenylpiperazine-1-Ium Dihydrogen Phosphate,” Journal of Molecular Structure 1207 (2020): 127762. doi:10.1016/j.molstruc.2020.127762
   Web of Science ®Google Scholar
• 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 and H. Nakatsuji, Gaussian09 Program (Wallingford, CT: Gaussian Inc., 2004).
   Google Scholar
• M. H. Jamroz, “Vibrational energy distribution analysis (VEDA): scopes and limitations.” Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 114 (2013): 220–30. doi:10.1016/j.saa.2013.05.096
   Google Scholar
• N. Sudha, R. Surendran, and S. Jeyaram, “Synthesis, Characterization, Linear and Nonlinear Optical Features of Novel Organic Compound Pyridylcarboxamide Chalcone for Nonlinear Optical Applications,” Optical Materials 131 (2022): 112668. doi:10.1016/j.optmat.2022.112668
   Web of Science ®Google Scholar
• R. Dennington, T. Keith, J. Millam, K. Eppinnett, W.L. Hovell and R. Gilliland, GaussView, Version 3.09 (Shawnee Mission, KS: Semichem Inc., 2003), 1.
   Google Scholar
• R. Srivastava, L. Sinha, M. Karabacak, O. Prasad, S. K. Pathak, A. M. Asiri, and M. Cinar, “Spectral Features, Electric Properties, NBO Analysis and Reactivity Descriptors of 2-(2-Benzothiazolylthio)-Ethanol: Combined Experimental and DFT Studies,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 136 (2015): 1205–15. doi:10.1016/j.saa.2014.09.091
   PubMed Web of Science ®Google Scholar
• A. Kechiche, T. Fradi, O. Noureddine, M. Guergueb, F. Loiseau, V. Guerineau, N. Issoui, A. Lemeune, and H. Nasri, “Synthesis, Characterization and Catalytic Studies of Chromium (III) Porphyrin Complex with Axial Cyanate Ligands,” Journal of Molecular Structure 1250 (2022): 131801. doi:10.1016/j.molstruc.2021.131801
   Web of Science ®Google Scholar
• A. Zochedh, A. Shunmuganarayanan, and A. Bahadur Sultan, “Conformational Fidelity and Hydrogen Bond Associability of L-Histidine with Sulfamate Anion Studied through XRD, Quantum Chemical, Spectroscopic and Molecular Docking Simulation as a Cdk-4 Inhibitor against Retinoblastoma,” Journal of Molecular Structure 1274 (2023): 134402. doi:10.1016/j.molstruc.2022.134402
   Web of Science ®Google Scholar
• D. E. V. Pires, T. L. Blundell, and D. B. Ascher, “pkCSM: Predicting Small-Molecule Pharmacokinetic and Toxicity Properties Using Graph-Based Signatures,” Journal of Medicinal Chemistry 58, no. 9 (2015): 4066–72. doi:10.1021/acs.jmedchem.5b00104
   PubMed Web of Science ®Google Scholar
• A. Daina, O. Michielin, and V. Zoete, “SwissADME: A Free Web Tool to Evaluate Pharmacokinetics, Drug-Likeness and Medicinal Chemistry Friendliness of Small Molecules,” Scientific Reports 7, no. 1 (2017): 42717. doi:10.1038/srep42717
   PubMed Web of Science ®Google Scholar
• H. M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T. N. Bhat, H. Weissig, I. N. Shindyalov, and P. E. Bourne, “The Protein Data Bank Nuclei c,” Nucleic Acids Research 28, no. 1 (2000): 235–42. doi:10.1093/nar/28.1.235
   PubMed Web of Science ®Google Scholar
• W. Tian, C. Chen, X. Lei, J. Zhao, and J. Liang, “CASTp 3.0: Computed Atlas of Surface Topography of Proteins,” Nucleic Acids Research 46, NO. W1 (2018): W363–7. doi:10.1093/nar/gky473
   PubMed Web of Science ®Google Scholar
• M. H. Jamróz, “Vibrational Energy Distribution Analysis (VEDA): Scopes and Limitations,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 114 (2013): 220–30. doi:10.1016/j.saa.2013.05.096
   PubMed Web of Science ®Google Scholar
• R. Dennington, T. Keith, and J. Millam, GaussView, Version 5 (Wallingford, CT: Gaussian Inc., 2009).
   Google Scholar
• G. Keresztury, J. M. Chalmers, and P. R. Griffith, “Raman Spectroscopy,” Theory in Handbook of Vibrational Spectroscopy, vol. 1. (Hoboken, NJ: John Wiey & Sons Ltd, 2002).
   Google Scholar
• 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., Gaussian09, Revision A (Wallingford, CT: Gaussian Inc., 2009), 150–66.
   Google Scholar
• K. Bhavani, S. Renuga, S. Muthu, and K. Sankara Narayanan, “Quantum Mechanical Study and Spectroscopic (FT-IR, FT-Raman, 13C, 1H) Study, First Order Hyperpolarizability, NBO Analysis, HOMO and LUMO Analysis of 2-Acetoxybenzoic Acid by Density Functional Methods,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 136 (2015): 1260–8. doi:10.1016/j.saa.2014.10.012
   PubMed Web of Science ®Google Scholar
• H. Ghalla, N. Issaoui, F. Bardak, and A. Atac, “Intermolecular Interactions and Molecular Docking Investigations on 4-Methoxybenzaldehyde,” Computational Materials Science 149 (2018): 291–300. doi:10.1016/j.commatsci.2018.03.042
   Web of Science ®Google Scholar
• S. Muthu, E. Elamurugu Porchelvi, M. Karabacak, A. M. Asiri, and S. S. Swathi, “Synthesis, Structure, Spectroscopic Studies (FT-IR, FT-Raman and UV), Normal Coordinate, NBO and NLO Analysis of Salicylaldehyde p-Chlorophenylthiosemicarbazone,” Journal of Molecular Structure 1081 (2015): 400–12. doi:10.1016/j.molstruc.2014.10.024
   Web of Science ®Google Scholar
• D. Lin-Vien, The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules (Amsterdam, Netherlands: Elsevier, 1991).
   Google Scholar
• A. Sagaama, and N. Issaoui, “Design, Molecular Docking Analysis of an anti-Inflammatory Drug, Computational Analysis and Intermolecular Interactions Energy Studies of 1-Benzothiophene-2-Carboxylic Acid,” Computational Biology and Chemistry 88 (2020): 107348. doi:10.1016/j.compbiolchem.2020.107348
   PubMed Web of Science ®Google Scholar
• E. H. Avdović, D. Milenković, J. M. Dimitrić Marković, J. Đorović, N. Vuković, M. D. Vukić, V. V. Jevtić, S. R. Trifunović, I. Potočňák, and Z. Marković, “Synthesis, Spectroscopic Characterization (FT-IR, FT-Raman, and NMR), Quantum Chemical Studies and Molecular Docking of 3-(1-(Phenylamino) Ethylidene)-Chroman-2, 4-Dione,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 195 (2018): 31–40. doi:10.1016/j.saa.2018.01.023
   PubMed Web of Science ®Google Scholar
• M. Tammer, “G. Sokrates: Infrared and Raman Characteristic Group Frequencies: Tables and Charts,” Colloid and Polymer Science 283, no. 2 (2004): 235. doi:10.1007/s00396-004-1164-6
   Google Scholar
• R. M. Asath, R. Premkumar, T. Mathavan, A. Milton Franklin Benial, “Structural, Spectroscopic and Molecular Docking Studies on 2-Amino-3-Chloro-5-Trifluoromethyl Pyridine: A Potential Bioactive Agent,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 175 (2017): 51–60.
   PubMed Web of Science ®Google Scholar
• G. Varsányi, Assignments for Vibrational Spectra of Seven Hundred Benzene Derivatives, vol. 1. (Hoboken, NJ: John Wiley & Sons, 1974).
   Google Scholar
• S. M. Hiremath, A. Suvitha, N. R. Patil, C. S. Hiremath, S. S. Khemalapure, S. K. Pattanayak, V. S. Negalurmath, K. Obelannavar, S. J. Armaković, and S. Armaković, “Synthesis of 5-(5-Methyl-Benzofuran-3-Ylmethyl)-3H-[1, 3, 4] Oxadiazole-2-Thione and Investigation of Its Spectroscopic, Reactivity, Optoelectronic and Drug Likeness Properties by Combined Computational and Experimental Approach,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 205 (2018): 95–110. doi:10.1016/j.saa.2018.07.003
   PubMed Web of Science ®Google Scholar
• S. M. Hiremath, A. Suvitha, N. R. Patil, C. S. Hiremath, S. S. Khemalapure, S. K. Pattanayak, V. S. Negalurmath, and K. Obelannavar, “Molecular Structure, Vibrational Spectra, NMR, UV, NBO, NLO, HOMO-LUMO and Molecular Docking of 2-(4, 6-Dimethyl-1-Benzofuran-3-yl) Acetic Acid (2DBAA): Experimental and Theoretical Approach,” Journal of Molecular Structure 1171 (2018): 362–374. doi:10.1016/j.molstruc.2018.05.109
   Web of Science ®Google Scholar
• N. Colthup, Introduction to Infrared and Raman Spectroscopy (Amsterdam, Netherlands: Elsevier, 2012).
   Google Scholar
• Q. S. Obu, H. Louis, J. O. Odey, I. J. Eko, S. Abdullahi, T. N. Ntui, and O. E. Offiong, “Synthesis, Spectra (FT-IR, NMR) Investigations, DFT Study, in Silico ADMET and Molecular Docking Analysis of 2-Amino-4-(4-Aminophenyl) Thiophene-3-Carbonitrile as a Potential anti-Tubercular Agent,” Journal of Molecular Structure 1244 (2021): 130880. doi:10.1016/j.molstruc.2021.130880
   Web of Science ®Google Scholar
• H. Beckers, H. Bürger, R. Eujen, B. Rempfer, and H. Oberhammer, “Vibrational Spectra and Normal Coordinate Analysis of CF3 Compounds: Part XLVII. Vibrational Spectra, Normal Coordinate Analysis and Electron Diffraction Investigation of CF3SiH3 and Its Deuterated Varieties,” Journal of Molecular Structure 140, no. 3–4 (1986): 281–301. doi:10.1016/0022-2860(86)87011-9
   Web of Science ®Google Scholar
• C. Alaşalvar, M. S. Soylu, H. Ünver, N. Ocak İskeleli, M. Yildiz, M. Çiftçi, and E. Banoğlu, “Crystal Structure and DFT Calculations of 5-(4-Chlorophenyl)-1-(6-Methoxypyridazin-3-yl)-1H-Pyrazole-3-Carboxylic Acid,” Spectrochimica Acta Part A, Molecular and Biomolecular Spectroscopy 132 (2014): 555–562. doi:10.1016/j.saa.2014.05.014
   PubMed Web of Science ®Google Scholar
• H. M. Refaat, and D. A. Noor El-Din, “Chemical and Biological Evaluation of Moxifloxacin-Benzimidazole Mixed Ligands Complexes: Anti-Cancer and anti-Oxidant Activities,” Journal of Molecular Structure 1163 (2018): 103–113. doi:10.1016/j.molstruc.2018.02.116
   Web of Science ®Google Scholar
• A. C. Ekennia, A. A. Osowole, L. O. Olasunkanmi, D. C. Onwudiwe, O. O. Olubiyi, and E. E. Ebenso, “Synthesis, Characterization, DFT Calculations and Molecular Docking Studies of Metal (II) Complexes,” Journal of Molecular Structure 1150 (2017): 279–292. doi:10.1016/j.molstruc.2017.08.085
   Web of Science ®Google Scholar
• A. C. Ekennia, A. A. Osowole, D. C. Onwudiwe, I. Babahan, C. U. Ibeji, S. N. Okafor, and O. T. Ujam, “Synthesis, Characterization, Molecular Docking, Biological Activity and Density Functional Theory Studies of Novel 1, 4‐Naphthoquinone Derivatives and Pd (II), Ni (II) and Co (II) Complexes,” Applied Organometallic Chemistry 32, no. 5 (2018): e4310. doi:10.1002/aoc.4310
   Web of Science ®Google Scholar
• A. Zochedh, M. Priya, C. Chakaravarthy, A. B. Sultan, and T. Kathiresan, “Experimental and Computational Evaluation of Syringic Acid–Structural, Spectroscopic, Biological Activity and Docking Simulation,” Polycyclic Aromatic Compounds 43, (2022): 1–33. doi:10.1080/10406638.2022.2118332
   Web of Science ®Google Scholar
• R. Premkumar, S. Hussain, T. Mathavan, K. Anitha, and A. M. F. Benial, “Surface-Enhanced Raman Scattering and Quantum Chemical Studies of 2-Trifluoroacetylpyrrole Chemisorbed on Colloidal Silver and Gold Nanoparticles: A Comparative Study,” Journal of Molecular Liquids 290 (2019): 111209. doi:10.1016/j.molliq.2019.111209
   Web of Science ®Google Scholar
• N. M. O’boyle, A. L. Tenderholt, and K. M. Langner, “Cclib: A Library for Package‐Independent Computational Chemistry Algorithms,” Journal of Computational Chemistry 29, no. 5 (2008): 839–845. doi:10.1002/jcc.20823
   PubMed Web of Science ®Google Scholar
• İ. Sıdır, Y. G. Sıdır, M. Kumalar, and E. Taşal, “Ab Initio Hartree–Fock and Density Functional Theory Investigations on the Conformational Stability, Molecular Structure and Vibrational Spectra of 7-Acetoxy-6-(2, 3-Dibromopropyl)-4, 8-Dimethylcoumarin Molecule,” Journal of Molecular Structure 964, no. 1–3 (2010): 134–151. doi:10.1016/j.molstruc.2009.11.023
   Web of Science ®Google Scholar
• V. Balachandran, and K. Parimala, “Tautomeric Purine Forms of 2-Amino-6-Chloropurine (N9H10 and N7H10): Structures, Vibrational Assignments, NBO Analysis, Hyperpolarizability, HOMO–LUMO Study Using B3 Based Density Functional Calculations,” Spectrochimica Acta Part A, Molecular and Biomolecular Spectroscopy 96 (2012): 340–351. doi:10.1016/j.saa.2012.05.050
   PubMed Web of Science ®Google Scholar
• A. Lakshmi, and V. Balachandran, “Rotational Isomers, NBO and Spectral Analyses of N-(2-Hydroxyethyl) Phthalimide Based on Quantum Chemical Calculations,” Journal of Molecular Structure 1033 (2013): 40–50. doi:10.1016/j.molstruc.2012.08.002
   Web of Science ®Google Scholar
• S. Sukumaran, A. Zochedh, T. M. Viswanathan, A. B. Sultan, and T. Kathiresan, “Theoretical Investigation of 5-Fluorouracil and Tamoxifen Complex–Structural, Spectrum, DFT, ADMET and Docking Simulation,” Polycyclic Aromatic Compounds, 43 (2023): 1–18. doi:10.1080/10406638.2022.2164018
   Web of Science ®Google Scholar
• A. Zochedh, K. Chandran, M. Priya, A. B. Sultan, and T. Kathiresan, “DFT Simulation of Berberine Chloride with Spectroscopic Characterization – Biological Activity and Molecular Docking against Breast Cancer,” Polycyclic Aromatic Compounds, 43 (2023): 1–25. doi:10.1080/10406638.2023.2201457
   Google Scholar
• M. Sathish, L. Rajasekaran, D. Shanthi, N. Kanagathara, S. Sarala, and S. Muthu, “Spectroscopic (FT-IR, FT-Raman, UV-Vis) Molecular Structure, Electronic, Molecular Docking, and Thermodynamic Investigations of Indole-3-Carboxylic Acid by DFT Method,” Journal of Molecular Structure 1234 (2021): 130182. doi:10.1016/j.molstruc.2021.130182
   Web of Science ®Google Scholar
• R. G. Parr, W. Yang Density Functional Theory of Atoms and Molecules (Oxford: Oxford University Press, 1989).
   Google Scholar
• P. P. Zamora, K. Bieger, A. Cuchillo, A. Tello, and J. P. Muena, “Theoretical Determination of a Reaction Intermediate: Fukui Function Analysis, Dual Reactivity Descriptor and Activation Energy,” Journal of Molecular Structure 1227 (2021): 129369. doi:10.1016/j.molstruc.2020.129369
   Web of Science ®Google Scholar
• I. B. Grillo, G. A. Urquiza-Carvalho, E. J. F. Chaves, and G. B. Rocha, “Semiempirical Methods Do Fukui Functions: Unlocking a Modeling Framework for Biosystems,” Journal of Computational Chemistry 41, no. 9 (2020): 862–873. doi:10.1002/jcc.26148
   PubMed Web of Science ®Google Scholar
• R. Pucci, and G. G. N. Angilella, “Density Functional Theory, Chemical Reactivity, and the Fukui Functions,” Foundations of Chemistry 24, no. 1 (2022): 59–71. doi:10.1007/s10698-022-09416-z
   Web of Science ®Google Scholar
• C. Morell, A. Grand, and A. Toro-Labbé, “New Dual Descriptor for Chemical Reactivity,” The Journal of Physical Chemistry A 109, no. 1 (2005): 205–212. doi:10.1021/jp046577a
   PubMed Web of Science ®Google Scholar
• D. A. Kleinman, “Nonlinear Dielectric Polarization in Optical Media,” Physical Review 126, no. 6 (1962): 1977–1979. doi:10.1103/PhysRev.126.1977
   Web of Science ®Google Scholar
• G. F. Jasmine, M. Amalanathan, and S. D. D. Roy, “Molecular Structure and Charge Transfer Contributions to Nonlinear Optical Property of 2-Methyl-4-Nitroaniline: A DFT Study,” Journal of Molecular Structure 1112 (2016): 63–70. doi:10.1016/j.molstruc.2016.02.013
   Web of Science ®Google Scholar
• A. Karakas, Y. Ceylan, M. Karakaya, M. Taser, B. B. Terlemez, N. Eren, Y. El Kouari, M. Lougdali, A. K. Arof, and B. Sahraoui, “Theoretical Diagnostics of Second and Third-Order Hyperpolarizabilities of Several Acid Derivatives,” Open Chemistry 17, no. 1 (2019): 151–156. doi:10.1515/chem-2019-0020
   Web of Science ®Google Scholar
• S. Li, R. Bu, R. Gou, and C. Zhang, “Hirshfeld Surface Method and Its Application in Energetic Crystals,” Crystal Growth & Design 21, no. 12 (2021): 6619–6634. doi:10.1021/acs.cgd.1c00961
   Web of Science ®Google Scholar
• P. R. Spackman, M. J. Turner, J. J. McKinnon, S. K. Wolff, D. J. Grimwood, D. Jayatilaka, and M. A. Spackman, “CrystalExplorer: A Program for Hirshfeld Surface Analysis, Visualization and Quantitative Analysis of Molecular Crystals,” Journal of Applied Crystallography 54, no. Pt 3 (2021): 1006–1011. doi:10.1107/S1600576721002910
   PubMedGoogle Scholar
• J. J. McKinnon, D. Jayatilaka, and M. A. Spackman, “Towards Quantitative Analysis of Intermolecular Interactions with Hirshfeld Surfaces,” Chemical Communications 37, no. 37 (2007): 3814–3816. doi:10.1039/b704980c
   Google Scholar
• A. L. Rohl, M. Moret, W. Kaminsky, K. Claborn, J. J. McKinnon, and B. Kahr, “Hirshfeld Surfaces Identify Inadequacies in Computations of Intermolecular Interactions in Crystals: Pentamorphic 1, 8-Dihydroxyanthraquinone,” Crystal Growth & Design 8, no. 12 (2008): 4517–4525. doi:10.1021/cg8005212
   Web of Science ®Google Scholar
• S. K. Wolff, et al., CrystalExplorer (Version 3.1) (Perth, Australia: University of Western Australia, 2012).
   Google Scholar
• A. Ali, M. Khalid, M. F. U. Rehman, S. Haq, A. Ali, M. N. Tahir, M. Ashfaq, F. Rasool, and A. A. C. Braga, “Efficient Synthesis, SC-XRD, and Theoretical Studies of O-Benzenesulfonylated Pyrimidines: Role of Noncovalent Interaction Influence in Their Supramolecular Network,” ACS Omega 5, no. 25 (2020): 15115–15128. doi:10.1021/acsomega.0c00975
   PubMed Web of Science ®Google Scholar
• P. Venkatesan, S. Thamotharan, A. Ilangovan, H. Liang, and T. Sundius, “Crystal Structure, Hirshfeld Surfaces and DFT Computation of NLO Active (2E)-2-(Ethoxycarbonyl)-3-[(1-Methoxy-1-Oxo-3-Phenylpropan-2-yl) Amino] Prop-2-Enoic Acid,” Spectrochimica Acta Part A, Molecular and Biomolecular Spectroscopy 153 (2016): 625–636. doi:10.1016/j.saa.2015.09.002
   PubMed Web of Science ®Google Scholar
• M. Khalid, A. Ali, S. Haq, M. N. Tahir, J. Iqbal, A. A. C. Braga, M.Ashfaq, and S. U. H. Akhtar, “O-4-Acetylamino-Benzenesulfonylated Pyrimidine Derivatives: Synthesis, SC-XRD, DFT Analysis and Electronic Behaviour Investigation,” Journal of Molecular Structure 1224 (2021): 129308. doi:10.1016/j.molstruc.2020.129308
   Web of Science ®Google Scholar
• A. Ali, A. Kuznetsov, M. U. Khan, M. N. Tahir, M. Ashfaq, A. R. Raza, and S. Muhammad, “2-Amino-6-Methylpyridine Based co-Crystal Salt Formation Using Succinic Acid: Single-Crystal Analysis and Computational Exploration,” Journal of Molecular Structure 1230 (2021): 129893. doi:10.1016/j.molstruc.2021.129893
   Web of Science ®Google Scholar
• R. Sharmili Banu, K. I. Mohana Priya, and A. S. Azar Zochedh, “Identification of Novel Bioactive Compounds from Banana Fruit (Musa Sapientum) as Antidepressant in Pregnant Women: Molecular Docking, Physiochemical and ADMET Evaluation,” Asian Journal of Biotechnology and Genetic Engineering 5 (2022): 9–24.
   Google Scholar
• K. Chandran, D. I. Shane, A. Zochedh, A. B. Sultan, and T. Kathiresan, “Docking Simulation and ADMET Prediction Based Investigation on the Phytochemical Constituents of Noni (Morinda Citrifolia) Fruit as a Potential Anticancer Drug,” In Silico Pharmacology 10, no. 1 (2022): 14. doi:10.1007/s40203-022-00130-4
   PubMedGoogle Scholar
• A. A. Zochedh, S. Asath Bahadur, and T. Kathiresan, “Quantum Chemical and Molecular Docking Studies of Naringin: A Potent anti-Cancer Drug,” Journal of Cardiovascular Disease Research 12 (2021): 1140–8.
   Google Scholar
• M. Priya, A. Zochedh, K. Chandran, K. Arumugam, S. Banu, C. Chakaravarthy, and A. B. Sultan, “Computer-Aided Analysis of Biochanin-A as a Potential Breast Cancer Drug Based on DFT, Molecular Docking, and Pharmacokinetic Studies,” Letters in Applied NanoBioScience 12, no. 4 (2023): 165.
   Google Scholar
• A. Zochedh, M. Priya, A. Shunmuganarayanan, K. Thandavarayan, and A. B. Sultan, “Investigation on Structural, Spectroscopic, DFT, Biological Activity and Molecular Docking Simulation of Essential Oil Gamma-Terpinene,” Journal of Molecular Structure 1268 (2022): 133651. doi:10.1016/j.molstruc.2022.133651
   Web of Science ®Google Scholar
• M. Priya, A. Zochedh, K. Arumugam, and A. B. Sultan, “Quantum Chemical Investigation, Drug-Likeness and Molecular Docking Studies on Galangin as Alpha-Synuclein Regulator for the Treatment of Parkinson’s Disease,” Chemistry Africa 6, no. 1 (2023): 287–309. doi:10.1007/s42250-022-00508-z
   Google Scholar
• A. Zochedh, K. Chandran, M. Priya, A. B. Sultan, and T. Kathiresan, “Molecular Simulation of Naringin Combined with Experimental Elucidation–Pharmaceutical Activity and Molecular Docking against Breast Cancer,” Journal of Molecular Structure 1285 (2023): 135403. doi:10.1016/j.molstruc.2023.135403
   Web of Science ®Google Scholar