References
- Malik, E. M.; Müller, C. E. Anthraquinones as Pharmacological Tools and Drugs. Medicinal Research Reviews 2016, 36(4), 705–748. DOI: https://doi.org/10.1002/med.21391.
- Fain, V.Y. 9,10-Antrakhinony i ikh primenenie (9,10-Anthraquinines and Their Aplication). 1999, Moscow, Tsentr Fotokhimii Ross. Akad. Nauk.
- Sendelbach, L. E. A Review of the Toxicity and Carcinogenicity of Anthraquinone Derivatives. Toxicology 1989, 57(3), 227–240. DOI: https://doi.org/10.1016/0300-483X(89)90113-3.
- Driscoll, J.S.; Hazard, G.F.; Wood, H.B.; Goldin, A. Structure-Antitumor Activity Relationships Among Quinone Derivatives. Cancer Chemotherapy Reports. Part 2 1974, 4(2), 1–362.
- Cudlin, J.; Blumauerova, M.; Steinerova, N.; Mateju, J.; Zalabak, V. Biological Activity of Hydroxyanthraquinones and Their Glucosides Toward Microorganisms. Folia Microbiological 1976, 21, 54–57. DOI: https://doi.org/10.1007/BF02879007.
- IARC Working Group on the Evaluation of Carcinogenic Risks to Humans. Some Chemicals Present in Industrial and Consumer Products, Food and Drinking-Water. IARC monographs on the evaluation of carcinogenic risks to humans: Lyon, France, 2013; 101,9 pp.
- Nollet, L. M. L.; Gutierrez-Uribe, J. A. Phenolic Compounds in Food Characterization and Analysis. CRC Press: New York, 2018; 1–430 pp.
- Schinazi, R. F.; Chu, C. K.; Babu, J. R.; Oswald, B. J.; Saalmann, V.; Cannon, D. L.; Eriksson, B.F.H.; Nasr, M. Anthraquinones as a New Class of Antiviral Agents Against Human Immunodeficiency Virus. Antiviral Research 1990, 13(5), 265–272. DOI: https://doi.org/10.1016/0166-3542(90)90071-E.
- Shrestha, J. P.; Subedi, Y. P.; Chen, L.; Chang, C. W. T. A Mode of Action Study of Cationic Anthraquinone Analogs: A New Class of Highly Potent Anticancer Agents. MedChemComm 2015, 6(11), 2012–2022. DOI: https://doi.org/10.1039/C5MD00314H.
- Taher, A.T.; Hegazy, G.H. Synthesis of Novel Bis-Anthraquinone Derivatives and their Biological Evaluation as Antitumor Agents. Archives of Pharmacal Research 2013, 36(5), 573–578. DOI: https://doi.org/10.1007/s12272-013-0074-x.
- Vanajothi, R.; Srinivasan, P. An Anthraquinone Derivative from Luffa acutangula Induces Apoptosis in Human Lung Cancer Cell Line NCI-H460 Through p53-Dependent Pathway. Journal of Receptor and Signal Transduction Research 2016, 36(3), 292–211. DOI: https://doi.org/10.3109/10799893.2015.1108335.
- Awasthi, P.; Vatsal, M.; Sharma, A. Structural and Biological Study of Synthesized Anthraquinone Series of Compounds with Sulfonamide Feature. Journal of Biomolecular Structure & Dynamics 2019, 37(17), 4465–4480. DOI: https://doi.org/10.1080/07391102.2018.1552198.
- Lin, S.; Zhang, Y.; Wang, Z.; Zhang, S.; Li, Y.; Fan, Y.; Li, D.; Li, S.; Bai, Y. Preparation of Novel Anthraquinone-Based Aspirin Derivatives with Anti-Cancer Activity. European Journal of Pharmacology 2021, 900 (2021), 174020. DOI: https://doi.org/10.1016/j.ejphar.2021.174020.
- Ozkok, F.; Sahin, Y. M. Biyoaktif Antrakinon Anologlarının Sentezine Yönelik Özgün Metot Geliştirilmesi, TÜRKIYE, Patent, TR 2016/19610.
- Gibson, D. Drug-DNA Interactions and Novel Drug Design. The Pharmacogenomics Journal 2002, 2(5), 275–276. DOI: https://doi.org/10.1038/sj.tpj.6500133.
- Çapan, İ.; Gümüş, M.; Gökce, H.; Çetin, H.; Sert, Y.; Koca, İ. Synthesis, Dielectric Properties, Molecular Docking and ADME Studies of Pyrrole-3-ones. Journal of Biomolecular Structure and Dynamics 2021, 1–17. DOI: https://doi.org/10.1080/07391102.2021.1914174.
- Gümüş, M.; Babacan, Ş. N.; Demir, Y.; Sert, Y.; Koca, İ.; Gülçin, İ. Discovery of Sulfadrug-Pyrrole Conjugates as Carbonic Anhydrase and Acetylcholinesterase Inhibitors. Archiv Der Pharmazie 2022, 355(1), e2100242. DOI: https://doi.org/10.1002/ardp.202100242.
- Clinical and Laboratory Standards Institute – CLSI 2000 Reference Method for Broth Dilution Antifungal Susceptbility Testing of Yeasts; Approved Standart M27-A NCCLS, Wayne, Pennsylvania.
- Clinical and Laboratory Standards Institute – CLSI 2012 Methods for Dilution Antimicrobial Susceptibility for Bacteria that Grow Aerobically: Approved Standard M7-A9. CLSI, Wayne, PA.
- Shao, Y.; Molnar, L. F.; Jung, Y.; Kussmann, J.; Ochsenfeld, C.; Brown, S. T.; Gilbert, A. T. B.; Slipchenko, L. V.; Levchenko, S. V.; O'Neill, D. P.; et al. Advances in Methods and Algorithms in a Modern Quantum Chemistry Program Package. Physical Chemistry Chemical Physics 2006, 8(27), 3172–3191. DOI: https://doi.org/10.1039/B517914A.
- Becke, A. D. Density‐Functional Thermochemistry. III. The Role of Exact Exchange. The Journal of Chemical Physics 1993, 98(7), 5648–5652. DOI: https://doi.org/10.1063/1.464913.
- Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery Jr, J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; et al. Gaussian 03, Revision C. 02. Gaussian, Inc.: Wallingford CT, 2004.
- Pulay, P.; Fogarasi, G.; Pongor, G.; Boggs, J. E.; Vargha, A. Combination of Theoretical Ab Initio and Experimental Information to Obtain Reliable Harmonic Force Constants. Scaled Quantum Mechanical (QM) Force Fields for Glyoxal, Acrolein, Butadiene, Formaldehyde, and Ethylene. Journal of the American Chemical Society 1983, 105(24), 7037–7047. DOI: https://doi.org/10.1021/ja00362a005.
- Sundius, T. Molvib-A Flexible Program for Force Field Calculations. Journal of Molecular Structure 1990, 218, 321–326. DOI: https://doi.org/10.1016/0022-2860(90)80287-T.
- Sundius, T. Scaling of ab Initio Force Fields by MOLVIB. Vibrational Spectroscopy 2002, 29(1–2), 89–95. DOI: https://doi.org/10.1016/S0924-2031(01)00189-8.
- Istvan, K. 2002. Simirra, A program for simulation of IR and Raman spectra, Budapest: Chemical Research Center(It was obtained from Dr. Gabor Keresztury in Chemical Research Center in Budapest).
- Celik, S.; Akyuz, S.; Ozel, A. E. Vibrational Spectroscopic Characterization and Structural Investigations of Cepharanthine, A Natural Alkaloid. Journal of Molecular Structure 2022, 1258, 132693. DOI: https://doi.org/10.1016/j.molstruc.2022.132693.
- Celik, S.; Kecel-Gunduz, S.; Akyuz, S.; Ozel, A. E. Structural Analysis, Spectroscopic Characterization and Molecular Docking Studies of the Cyclic Heptapeptide. Journal of Biomolecular Structure & Dynamics 2018, 36(9), 2407–2423. DOI: https://doi.org/10.1080/07391102.2017.1356240.
- Trott, O.; Olson, A. J. AutoDock Vina: Improving the Speed and Accuracy of Docking with a New Scoring Function, Efficient Optimization, and Multithreading. Journal of Computational Chemistry 2010, 31(2), 455–461. DOI: https://doi.org/10.1002/jcc.21334.
- Clinical and Laboratory Standards Institute - CLSI. Performance standards for antimicrobial susceptibility testing, M100-S25. CLSI, Wayne, PA, 2016.
- Nakagawa, H.; Kitamura, C. Crystal Structures of 1-hy-droxy-4-prop-yloxy-9,10-Anthra-Quinone and its Acetyl Derivative. Acta Crystallographica. Section E, Crystallographic Communications 2017, 73(Pt 12), 1845–1849. DOI: https://doi.org/10.1107/S2056989017015973.
- Wnuk, E.; Niedziałkowski, P.; Trzybiński, D.; Ossowski, T. 1-(Piperidin-1-yl)-9,10-anthraquinone . Acta Crystallographica. Section E, Structure Reports Online 2012, 68(Pt 10), o2879. DOI: https://doi.org/10.1107/S1600536812037713.
- Ranjitha, S.; Aroulmoji, V.; Mohr, T.; Anbarasan, P.M.; Rajarajan, G. Structural and Spectral Properties of 1,2-dihydroxy-9,10-anthraquinone Dye Sensitizer for Solar Cell Applications. Acta Physica Polonica A 2014, 126(3), 833–839. DOI: https://doi.org/10.12693/APhysPolA.126.833.
- Gribov, L. A.; Zubkova, O. B.; Sigarev, A. A. Theoretical Analysis of Infrared Spectrum of 9, 10-anthraquinone Molecule. Journal of Structural Chemistry 1993, 34(1), 147–154. DOI: https://doi.org/10.1007/BF00745414.
- Ball, B.; Zhou, X.; Liu, R. Density Functional Theory Study of Vibrational Spectra. 8. Assignment of Fundamental Vibrational Modes of 9, 10-anthraquinone and 9, 10-anthraquinone-d8. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 1996, 52(14), 1803–1814. DOI: https://doi.org/10.1016/S0584-8539(96)01769-2.
- Berezin, K. V.; Krivokhizhina, T. V.; Nechaev, V. V. Atypical Intensity Distribution in the Raman Spectrum of 9, 10-anthraquinone. Optics and Spectroscopy 2004, 97(4), 530–536. DOI: https://doi.org/10.1134/1.1813693.
- Beckford, S. J.; Dixon, D.W. Molecular Dynamics of Anthraquinone DNA Intercalators with Polyethylene Glycol Side Chains. Journal of Biomolecular Structure and Dynamics 2012, 29(5), 1065–1080. DOI: https://doi.org/10.1080/073911012010525031.
- Pecile, C.; Lunelli, B. Polirized Infrared Spectra of Single Crystals of 9,10 Anthraquinone and 9,10 Anthraquinone-d8. Journal of Chemical Physics. 1967, 46(6), 2109–2118. DOI: https://doi.org/10.1063/1.1841008.
- Celik, S.; Ozkok, F.; Ozel, A. E.; Müge Sahin, Y.; Akyuz, S.; Sigirci, B. D.; Kahraman, B. B.; Darici, H.; Karaoz, E. Synthesis, FT-IR and NMR Characterization, Antimicrobial Activity, Cytotoxicity and DNA Docking Analysis of a New Anthraquinone Derivate Compound. Journal of Biomolecular Structure & Dynamics 2020, 38(3), 756–770. DOI: https://doi.org/10.1080/07391102.2019.1587513.
- Roeges, N. P. A Guide to the Complete Interpretation of Infrared Spectra of Organic Structures. Wiley: New York, NY, 1994.
- Mary, Y. S.; Ushakumari, L.; Harikumar, B.; Varghese, H. T.; Panicker, C. Y. FT-IR, FT-Raman and SERS Spectra of L-proline. Journal of the Iranian Chemical Society 2009, 6(1), 138–144. DOI: https://doi.org/10.1007/BF03246512.
- Padmaja, L.; Ravikumar, C.; James, C.; Jayakumar, V. S.; Joe, I. H. Analysis of Vibrational Spectra of l-Alanylglycine Based on Density Functional Theory Calculations. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 2008, 71(1), 252–262. DOI: https://doi.org/10.1016/j.saa.2007.12.019.
- Dikmen, G. 1-(4-chlorophenyl) Piperazine: FT-IR, Raman, NMR and Theoretical Studies. Anadolu University Journal of Science and Technology-A Applied Sciences and Engineering 2019, 20(2), 133–142. DOI: https://doi.org/10.18038/aubtda.376154.
- Gunasekaran, S.; Anita, B. Spectral Investigation and Normal Coordinate Analysis of Piperazine. Indian Journal of Pure & Applied Physics 2008, 46(12), 833–838.
- Mendham, A. P.; Dines, T. J.; Snowden, M. J.; Chowdhry, B. Z.; Withnall, R. Vibrational Spectroscopy and DFT Calculations of Di‐Amino Acid Cyclic Peptides. Part I: cyclo (Gly‐Gly), cyclo (L‐Ala‐L‐Ala) and cyclo (L‐Ala‐Gly) in the Solid State and in Aqueous Solution. Journal of Raman Spectroscopy 2009, 40(11), 1478–1497. DOI: https://doi.org/10.1002/jrs.2293.
- Mendham, A. P.; Dines, T. J.; Snowden, M. J.; Withnall, R.; Chowdhry, B. Z. IR/Raman Spectroscopy and DFT Calculations of Cyclic Di‐Amino Acid Peptides. Part III: Comparison of Solid State and Solution Structures of Cyclo (L‐Ser‐L‐Ser). Journal of Raman Spectroscopy 2009, 40(11), 1508–1520. DOI: https://doi.org/10.1002/jrs.2306.
- Celik, S.; Ozkok, F.; Ozel, A. E.; Cakir, E.; Akyuz, S. Synthesis, FT-IR and NMR Characterization, Antibacterial and Antioxidant Activities, and DNA Docking Analysis of a New Vanillin-Derived imine Compound. Journal of Molecular Structure 2021, 1236, 130288. DOI: https://doi.org/10.1016/j.molstruc.2021.130288.
- Suresh, C.H.; Remya, G.S.; Anjalikrishna, P.K. Molecular Electrostatic Potential Analysis: A Powerful Tool to Interpret and Predict Chemical Reactivity. WIREs Computational Molecular Science 2022, e1601. DOI: https://doi.org/10.1002/wcms.1601.
- Kutlu, E.; Emen, F. M.; Kismali, G.; Kınaytürk, N. K.; Karacolak, A. I.; Kilic, D.; Asim Ali, M.; Kutlu, H. M.; Demirdogen, R. E. Synthesis and Investigation of In Vitro Cytotoxic Activities and Thermal Stability of Novel Pyridine Derivative Platinum (II) Complexes vis a vis DFT Studies. Polyhedron 2021, 210, 115492. DOI: https://doi.org/10.1016/j.poly.2021.115492.
- Pearson, R. G. 1973. Hard and Soft Acids and Bases (Vol. 2): Van Nostrand Reinhold: New York, NY.
- Patra, D.; Paul, S.; Sepay, N.; Kundu, R.; Ghosh, T. Structure-Activity Relationship on DNA Binding and Anticancer Activities of a Family of Mixed-Ligand oxidovanadium(V) Hydrazone Complexes. Journal of Biomolecular Structure & Dynamics 2018, 36(16), 4143–4155. DOI: https://doi.org/10.1080/07391102.2017.1409652.
- Kumar, A.; Srivastava, A. K.; Gangwar, S.; Misra, N.; Mondal, A.; Brahmachari, G. Combined Experimental (FT-IR, UV–Visible Spectra, NMR) and Theoretical Studies on the Molecular Structure, Vibrational Spectra, HOMO, LUMO,MESP Surfaces, Reactivity Descriptor and Molecular Docking of Phomarin. Journal of Molecular Structure 2015, 1096, 94–101. DOI: https://doi.org/10.1016/j.molstruc.2015.04.031.
- Maranda-Niedbała, A.; Krzyżewska, K.; Kotwica, K.; Skórka, Ł.; Drapała, J.; Jarzembska, K. N.; Zagórska, M.; Proń, A.; Nowakowski, R. 9,10-Anthraquinones Disubstituted with Linear Alkoxy Groups: Spectroscopy, Electrochemistry, and Peculiarities of Their 2D and 3D Supramolecular Organizations. Langmuir: The ACS Journal of Surfaces and Colloids 2020, 36(49), 15048–15063. DOI: https://doi.org/10.1021/acs.langmuir.0c02586.
- Kucuk, C.; Yurdakul, S.; Erdem, B. Experimental and Theoretical Fourier Transform Infrared and Raman Spectroscopy, Density Functional Theory, Antibacterial Activity and Molecular Docking Studies on 1-(4-methoxyphenyl)-1H-imidazole. Chemical Papers 2022, 1–22. DOI: https://doi.org/10.1007/s11696-021-02017-8.
- Qiu, S.; Tan, X.; Wu, K.; Zhang, A.; Han, S.; Wang, L. Experimental and Theoretical Study on Molecular Structure and FT-IR, Raman, NMR Spectra of 4,4'-dibromodiphenyl Ether. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 2010, 76(5), 429–434. DOI: https://doi.org/10.1016/j.saa.2009.10.005.
- Ajayi, T. J.; Shapi, M. Hirshfeld Surface Analysis and DFT Studies on Molecular Structure, Vibrational Spectra, NMR Chemical Shifts and NBO Analysis of Bis (2-hydroxyethyl (phenyl) carbamodithioate) Nickel (II). Journal of Molecular Structure 2019, 1197, 308–317. DOI: https://doi.org/10.1016/j.molstruc.2019.07.060.
- Zhang, Z.-P.; Yin, Z.-F.; Li, J.-Y.; Wang, Z.-P.; Wu, Q.-J.; Wang, J.; Liu, Y.; Cheng, M.-S. Synthesis, Molecular Docking Analysis, and Carbonic Anhydrase Inhibitory Evaluations of Benzenesulfonamide Derivatives Containing Thiazolidinone. Molecules 2019, 24(13), 2418. DOI: https://doi.org/10.3390/molecules24132418.
- Al-Otaibi, J. S.; Spittle, P. T.; El Gogary, T. M. Interaction of Anthraquinone Anti-Cancer Drugs with DNA: Experimental and Computational Quantum Chemical Study. Journal of Molecular Structure 2017, 1127, 751–760. DOI: https://doi.org/10.1016/j.molstruc.2016.08.007.
- Ansari, S. S.; Khan, R. H.; Naqvi, S. Probing the Intermolecular Interactions into Serum Albumin and Anthraquinone Systems: A Spectroscopic and Docking Approach. Journal of Biomolecular Structure & Dynamics 2018, 36(13), 3362–3375. DOI: https://doi.org/10.1080/07391102.2017.1388284.
- Drew, H. R.; Wing, R. M.; Takano, T.; Broka, C.; Tanaka, S.; Itakura, K.; Dickerson, R. E. Structure of a B-DNA Dodecamer: Conformation and Dynamics. Proceedings of the National Academy of Sciences of the United States of America 1981, 78(4), 2179–2183. DOI: https://doi.org/10.1073/pnas.78.4.2179.
- Celik, S.; Yilmaz, G.; Ozel, A. E.; Akyuz, S. Structural and Spectral Analysis of Anticancer Active Cyclo (Ala–His) Dipeptide. Journal of Biomolecular Structure & Dynamics 2022, 40(2), 660–613. DOI: https://doi.org/10.1080/07391102.2020.1817150.
- Celik, S.; Albayrak, A. T.; Akyuz, S.; Ozel, A. E.; Sigirci, B. D. Synthesis, Antimicrobial Activity, Molecular Docking and ADMET Study of a Caprolactam-Glycine Cluster. Journal of Biomolecular Structure & Dynamics 2021, 39(7), 2376–2386. DOI: https://doi.org/10.1080/07391102.2020.1748112.
- Eğlence-Bakır, S.; Celik, S.; Şahin, M.; Ozel, A. E.; Akyuz, S.; Ülküseven, B. Synthesis, Molecular Modelling, FT-IR, Raman and NMR Characterization, Molecular Docking and ADMET Study of New Nickel(II) Complex with an N4-tetradentate Thiosemicarbazone. Journal of Biomolecular Structure & Dynamics 2021, 39(12), 4212–4224. DOI: https://doi.org/10.1080/07391102.2020.1775128.
- Akalin, E.; Celik, S.; Akyuz, S. Molecular Modeling, Dimer Calculations, Vibrational Spectra, and Molecular Docking Studies of 5-Chlorouracil. Journal of Applied Spectroscopy 2020, 86(6), 975–985. DOI: https://doi.org/10.1007/s10812-020-00926-2.
- Lan, J.; Ge, J.; Yu, J.; Shan, S.; Zhou, H.; Fan, S.; Zhang, Q.; Shi, X.; Wang, Q.; Zhang, L. Structure of the SARS-CoV-2 Spike Receptor-Binding Domain Bound to the ACE2 Receptor. Nature 2020, 581(7807), 215–220. DOI: https://doi.org/10.1038/s41586-020-2180-5.
- Jin, Z.; Du, X.; Xu, Y.; Deng, Y.; Liu, M.; Zhao, Y.; Zhang, B.; Li, X.; Zhang, L.; Peng, C. Structure of Mpro from SARS-CoV-2 and Discovery of its Inhibitors. Nature 2020, 582(7811), 289–293. DOI: https://doi.org/10.1038/s41586-020-2223-y.
- Zhang, B.; Zhao, Y.; Jin, Z.; Liu, X.; Yang, H.; Rao, Z. The Crystal Structure of COVID- 19 Main Protease in Apo Form. 2020. DOI: https://doi.org/10.2210/pdb6M03/pdb.
- Walls, A. C.; Park, Y. J.; Tortorici, M. A.; Wall, A.; McGuire, A. T.; Veesler, D. Structure, Function, and Antigenicity of the SARS-CoV-2 Spike Glycoprotein. Cell 2020, 181(2), 281–292. DOI: https://doi.org/10.1016/j.cell.2020.02.058.
- Jurcik, A.; Bednar, D.; Byska, J.; Marques, S. M.; Furmanova, K.; Daniel, L.; Kokkonen, P.; Brezovsky, J.; Strnad, O.; Stourac, J.; et al. CAVER Analyst 2.0: Analysis and Visualization of Channels and Tunnels in Protein Structures and Molecular Dynamics Trajectories. Bioinformatics 2018, 34(20), 3586–3588. DOI: https://doi.org/10.1093/bioinformatics/bty386.