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Research Articles

Spectroscopic Characterization, Quantum Chemical and Molecular Docking Studies on 1-Chloroanthraquinone: A Novel Oral Squamous Cell Carcinoma Drug

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Pages 1816-1834 | Received 07 Sep 2022, Accepted 25 Apr 2023, Published online: 09 May 2023

References

  • S. Patai, and Z. Rappaport, The Chemistry of Quinonoid Compounds, vol. 2. (New York: Wiley, 1988).
  • T. P. Pathak, and M. S. Sigman, “Applications of Ortho-Quinone Methide Intermediates in Catalysis and Asymmetric Synthesis,” The Journal of Organic Chemistry 76, no. 22 (2011): 9210–5. doi:10.1021/jo201789k
  • R. H. Thomson, Naturally Occurring Quinones. (London: Chapman and Hall, 1987).
  • H. Dave, and L. Ledwani, “A Review on Anthraquinones Isolated from Cassia Species and Their Applications,” Indian Journal of Natural Products and Resources 3 (2015): 291–19.
  • J. Duval, V. Pecher, M. Poujol, and E. Lesellier, “Research Advances for the Extraction, Analysis and Uses of Anthraquinones: A Review,” Industrial Crops and Products 94 (2016): 812–33. doi:10.1016/j.indcrop.2016.09.056
  • D. S. Seigler, Plant Secondary Metabolism. (New York: Springer Science & Business Media, 2012).
  • A. Tikhomirov, A. Shtil, and A. Shchekotikhin, “Advances in the Discovery of Anthraquinone Based Anticancer Agents,” Recent Patents on anti-Cancer Drug Discovery 13, no. 2 (2018): 159–83. doi:10.2174/1574892813666171206123114
  • F. Tutin, and H. W. B. Clewer, “XCIX. The Constituents of Rhubarb,” Journal of the Chemical Society, Transactions 99 (1911): 946–67. doi:10.1039/CT9119900946
  • T. Cha, L. Qiu, C. Chen, Y. Wen, and M. Hung, “Emodin Down Regulates Androgen Receptor and Inhibits Prostate Cancer Cell Growth,” Cancer Research 65, no. 6 (2005): 2287–95. doi:10.1158/0008-5472.CAN-04-3250
  • S. Lin, W. Lai, C. Ho, F.-S. Yu, G.-W. Chen, J.-S. Yang, K.-C. Liu, M.-L. Lin, P.-P. Wu, M.-J. Fan, et al, “Emodin Induces Apoptosis of Human Tongue Squamous Cancer SCC-4 Cells through Reactive Oxygen Species and Mitochondria-Dependent Pathways,” Anticancer Research 29 (2009): 327–35.
  • L. C. Chang, H. M. Sheu, Y. S. Huang, T. R. Tsai, and K. W. Kuo, “A Novel Function of Emodin: Enhancement of the Nucleotide Excision Repair of UV- and Cisplatin-Induced DNA Damage in Human Cells,” Biochemical Pharmacology 58, no. 1 (1999): 49–57. doi:10.1016/s0006-2952(99)00075-1
  • Y. Ding, L. Zhao, H. Mei, S.-L. Zhang, Z.-H. Huang, Y.-Y. Duan, and P. Ye, “Exploration of Emodin to Treat Alphanaphthylisothiocyanate-Induced Cholestatic Hepatitis via anti-Inflammatory Pathway,” European Journal of Pharmacology 590, no. 1–3 (2008): 377–86. doi:10.1016/j.ejphar.2008.06.044
  • Y. Octavia, C. G. Tocchetti, K. L. Gabrielson, S. Janssens, H. J. Crijns, and A. L. Moens, “Doxorubicin-Induced Cardiomyopathy: From Molecular Mechanisms to Therapeutic Strategies,” Journal of Molecular and Cellular Cardiology 52, no. 6 (2012): 1213–25. doi:10.1016/j.yjmcc.2012.03.006
  • A. P. Krapcho, Z. Getahun, K. L. Avery, K. J. Vargas, M. P. Hacker, S. Spinelli, G. Pezzoni, and C. Manzotti, “Synthesis and Antitumor Evaluations of Symmetrically and Unsymmetrically Substituted 1,4-Bis[(Aminoalkyl)Amino]Anthracene-9,10-Diones and 1,4-Bis[(Aminoalkyl)Amino]-5,8-Dihydroxyanthracene-9,10-Diones,” Journal of Medicinal Chemistry 34, no. 8 (1991): 2373–80. doi:10.1021/jm00112a009
  • C. Monneret, “Recent Developments in the Field of Antitumour Anthracyclines,” European Journal of Medicinal Chemistry 36, no. 6 (2001): 483–93. doi:10.1016/s0223-5234(01)01244-2
  • E. Fan, W. Shi, and T. L. Lowary, “Synthesis of Daunorubicin Analogues Containing Truncated Aromatic Cores and Unnatural Monosaccharide Residues,” The Journal of Organic Chemistry 72, no. 8 (2007): 2917–28. doi:10.1021/jo062542q
  • R. C. Pandey, M. W. Toussaint, J. C. McGuire, and M. C. Thomas, “Maggiemycin and Anhydromaggiemycin: Two Novel Anthracyclinone Antitumor Antibiotics. Isolation, Structures, Partial Synthesis and Biological Properties,” The Journal of Antibiotics 42, no. 11 (1989): 1567–77. doi:10.7164/antibiotics.42.1567
  • A. R. Han, J. W. Park, M. K. Lee, Y. H. Ban, Y. J. Yoo, E. J. Kim, E. Kim, B.-G. Kim, J. K. Sohng, and Y. J. Yoon, “Development of a Streptomyces venezuelae-Based Combinatorial 23 Biosynthetic System for the Production of Glycosylated Derivatives of Doxorubicin and Its Biosynthetic Intermediates,” Applied and Environmental Microbiology 77, no. 14 (2011): 4912–23. doi:10.1128/AEM.02527-10
  • R. Thomson, Naturally Occurring Quinones, 2nd ed. (London, New York: Academic Press, 1971).
  • K. Hunger, Industrial Dye: Chemistry, Properties, Applications. (Weinheim: WILEY-VCH, 2003).
  • D. Jacquemin, V. Wathelet, J. Preat, and E. A. Perpète, “Ab Initio Tools for the Accurate Prediction of the Visible Spectra of Anthraquinones,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 67, no. 2 (2007): 334–41. doi:10.1016/j.saa.2006.07.023
  • J. W. Lown, “Anthracycline and Anthraquinone Anticancer Agents: Current Status and Recent Developments,” Pharmacology & Therapeutics 60, no. 2 (1993): 185–14.
  • M. J. Pang, Z. Yang, X. L. Zhang, Z. F. Liu, J. Fan, and H. Y. Zhang, “Physcion, a Naturally Occurring Anthraquinone Derivative, Induces Apoptosis and Autophagy in Human Nasopharyngeal Carcinoma,” Acta Pharmacologica Sinica 37, no. 12 (2016): 1623–40. doi:10.1038/aps.2016.98
  • P. Fan, A. E. Hay, A. Marston, H. Lou, and K. Hostettmann, “Chemical Variability of the Invasive Neophytes Polygonum Cuspidatum Sieb. and Zucc. and Polygonum Sachalinensis F. Schmidt Ex Maxim,” Biochemical Systematics and Ecology 37, no. 1 (2009): 24–34. doi:10.1016/j.bse.2008.11.018
  • S. Celik, F. Ozkok, A. E. Ozel, Y. M. Sahin, S. Akyuz, B. Diren Sigirci, B. Basaran Kahraman, H. Darici, and E. Karaoz, “Synthesis, FT-IR and NMR Characterization, Antimicrobial Activity, Cytotoxicity and DNA Docking Analysis of a New Anthraquinone Derivate Compound,” Journal of Biomolecular Structure & Dynamics 38, no. 3 (2020): 756–70. doi:10.1080/07391102.2019.1587513
  • R. Renjith, Y. Sheena Mary, H. T. Varghese, C. Yohannan Panicker, T. Thiemann, A. Shereef, and A. A. Al-Saadi, “Spectroscopic Investigation (FT-IR and FT-Raman), Vibrational Assignments, HOMO-LUMO Analysis and Molecular Docking Study of 1-Hydroxy-4,5,8- 25 Tris(4-Methoxyphenyl) Anthraquinone,” Journal of Physics and Chemistry of Solids 87 (2015): 110–21. doi:10.1016/j.jpcs.2015.07.024
  • T. Valarmathi, R. Premkumar, and A. Milton. Franklin Benial, “Spectroscopic and Molecular Docking Studies on 1- Hydroxyanthraquinone: A Potent Ovarian Cancer Drug,” Journal of Molecular Structure 1213 (2020): 128163. doi:10.1016/j.molstruc.2020.128163
  • T. Valarmathi, R. Premkumar, and A. Milton Franklin Benial, “Quantum Chemical and Molecular Docking Studies on 1,4-Bis(Methylamino)Anthraquinone: A DFT Approach” (AIP Conference Proceedings 2270, 2020): 040001.
  • T. Valarmathi, R. Premkumar, S. Christopher Jeyaseelan, A. Milton Franklin Benial, M. A. Palafox, and V. K. Rastogi, “Structural, Vibrational Spectroscopic and Molecular Docking Studies on 1-(Methylamino) Anthraquinone,” Asian Journal of Physics 27, no. 6 (2018): 317–37.
  • Y. Song, J. Lim, and Y. H. Seo, “A Novel Class of Anthraquinone-Based HDAC6 Inhibitors,” European Journal of Medicinal Chemistry 164 (2019): 263–72. doi:10.1016/j.ejmech.2018.12.056
  • E. De Moliner, S. Moro, S. Sarno, G. Zagotto, G. Zanotti, L. A. Pinna, and R. Battistutta, “Inhibition of Protein Kinase CK2 by Anthraquinone-Related Compounds. A Structural Insight,” The Journal of Biological Chemistry 278, no. 3 (2003): 1831–6. doi:10.1074/jbc.M209367200
  • H. P. Kuo, T. C. Chuang, M. H. Yeh, S.-C. Hsu, T.-D. Way, P.-Y. Chen, S.-S. Wang, Y.-H. Chang, M.-C. Kao, and J.-Y. Liu, “Growth Suppression of HER2-Overexpressing Breast Cancer Cells by Berberine via Modulation of the HER2/PI3K/Akt Signaling Pathway,” Journal of Agricultural and Food Chemistry 59, no. 15 (2011): 8216–24. doi:10.1021/jf2012584
  • R. Vanajothi, and P. Srinivasan, “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 36 (2016): 292–302.
  • A. T. Negmeldin, G. Padige, A. V. Bieliauskas, and M. K. H. Pflum, “Structural Requirements of HDAC Inhibitors: SAHA Analogues Modified at the C2 Position Display HDAC6/8 Selectivity,” ACS Medicinal Chemistry Letters 8, no. 3 (2017): 281–6. doi:10.1021/acsmedchemlett.6b00124
  • R. Hamacher, D. Saur, R. Fritsch, M. Reichert, R. M. Schmid, and G. Schneider, “Casein Kinase II Inhibition Induces Apoptosis in Pancreatic Cancer Cells,” Oncology Reports 18 (2007): 695–701. doi:10.3892/or.18.3.695
  • Q. Huang, G. Lu, H.-M. Shen, M. C. M. Chung, and C. Nam. Ong, “Anti-Cancer Properties of Anthraquinones from Rhubarb,” Medicinal Research Reviews 27, no. 5 (2007): 609–30. doi:10.1002/med.20094
  • 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
  • N. Dege, H. Gökce, O. Erman Doğan, G. Alpaslan, T. Ağar, S. Muthu, and Y. Sert, “Quantum Computational, Spectroscopic Investigations on N-(2-((2-Chloro-4,5-Dicyanophenyl)Amino)Ethyl)-4-Methylbenzenesulfonamide by DFT/TD-DFT with Different Solvents, Molecular Docking and Drug-Likeness Researches,” Colloids and Surfaces A 638 (2022): 128311. doi:10.1016/j.colsurfa.2022.128311
  • Jamelah S.Al-Otaibi, YSheena Mary, YShyma Mary, Sanja J. Armaković, Stevan Armaković, Christian Van Alsenoy, and H. S. Yathirajan, “Insights into the Reactivity Properties, Docking, DFT and MD Simulations of Orphenadrinium Dihydrogen Citrate in Different Solvents,” Journal of Molecular Liquids 367 (2022): 120583. doi:10.1016/j.molliq.2022.120583
  • H. A. Al-Ghulikah, A. A. Al-Mutairi, H. M. Hassan, A. A. Emam, Y. S. Mary, Y. S. Mary, S. Armaković, and S. J. Armaković, “Reactivity Properties and Adsorption Behavior of a Triazole Derivative – DFT and MD Simulation Studies,” Journal of Molecular Liquids 341 (2021): 117439. doi:10.1016/j.molliq.2021.117439
  • M. J. Frisch, G. W. Trucks, and H. B. Schlegel, Gaussian 09, Revision C. 02. (Wallingford CT: Gaussian Inc., 2009).
  • N. Akram, A. Mansha, R. Premkumar, A. M. Franklin Benial, S. Asim, S. Z. Iqbal, and H. S. Ali, “Spectroscopic, Quantum Chemical and Molecular Docking Studies on 2,4-Dimethoxy-1,3,5-Triazine: A Potent Inhibitor of Protein Kinase CK2 for the Development of Breast Cancer Drug,” Molecular Simulation 46, no. 17 (2020): 1340–53. doi:10.1080/08927022.2020.1822526
  • 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): 839–45. doi:10.1002/jcc.20823
  • M. H. Jamroz, Vibrational Energy Distribution Analysis VEDA 4.0 Program. (Warsaw, 2004).
  • Gauss View, Version 5, Ray Dennington, Todd Keith and John Milam. (Shawnee: Semichem Inc., 2009).
  • P. Niedziałkowski, J. Narloch, D. Trzybiński, and T. Ossowski, “1-Dimethylamino-9,10- Anthraquinone,” Acta Crystallographica Section E Structure Reports Online 67, no. 3 (2011): o723. doi:10.1107/S1600536811006829
  • S. Christopher Jeyaseelan, R. Premkumar, K. Kaviyarasu, and A. Milton Franklin Benial, “Spectroscopic, Quantum Chemical, Molecular Docking and in Vitro Anticancer Activity Studies on 5-Methoxyindole-3-Carboxaldehyde,” Journal of Molecular Structure 1197 (2019): 134–46. doi:10.1016/j.molstruc.2019.07.042
  • R. Premkumar, S. Hussain, S.-J. Koyambo-Konzapa, N. D. Jayram, M. R. Meera, T. Mathavan, and A. M. F. Benial, “SERS and DFT Studies of 2-(Trichloroacetyl) Pyrrole Chemisorbed on the Surface of Silver and Gold Coated Thin Films: In Perspective of Biosensor Applications,” Journal of Molecular Recognition 34, no. 11 (2021): e2921. doi:10.1002/jmr.2921
  • V. Arjunan, S. Thillai Govindaraja, A. Jayapraksh, and S. Mohan, “Structural, Vibrational and Nuclear Magnetic Resonance Investigations of 4-Bromoisoquinoline by Experimental and Theoretical DFT Methods,” Spectrochimica Acta Part A, Molecular and Biomolecular Spectroscopy 107 (2013): 62–71. doi:10.1016/j.saa.2013.01.037
  • S. Sebastian, S. Sylvestre, N. Sundaraganesan, M. Amalanathan, S. Ayyapan, K. Oudayakumar, and B. Karthikeyan, “Vibrational Spectra, Molecular Structure, Natural Bond Orbital, First Order Hyperpolarizability, TD-DFT and Thermodynamic Analysis of 4-Amino-3- Hydroxy-1-Naphthalenesulfonic Acid by DFT Approach,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 107 (2013): 167–78. doi:10.1016/j.saa.2013.01.041
  • L. J. Bellamy, The Infra-Red Spectra of Complex Molecules. (New York: John Wiley and Sons, Inc., 1975).
  • M. Anuratha, A. Jawahar, M. Umadevi, V. G. Sathe, P. Vanelle, T. Terme, V. Meenakumari, and A. Milton Franklin Benial, “SERS Investigations of 2,3-Dibromo-1,4-Naphthoquinone on Silver Nanoparticles,” Spectrochimica Acta Part A, Molecular and Biomolecular Spectroscopy 105 (2013): 218–22. doi:10.1016/j.saa.2012.12.028
  • R. N. Medhi, R. Barman, K. C. Medhi, and S. S. Jois, “Ultraviolet Absorption and Vibrational Spectra of 2-Fluoro-5-Bromopyridine,” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 56, no. 8 (2000): 1523–32. doi:10.1016/S1386-1425(99)00275-9
  • K. C. Medhi, “Infrared and Raman Spectra and Thermodynamic Functions of 4- Methoxypyridine N-Oxide,” Proceedings/Indian Academy of Sciences 91, no. 2 (1982): 137–44. doi:10.1007/BF02861097
  • G. Varsanyi, Assignments for Vibrational Spectra of Seven Hundred Benzene Derivatives, vol. 1. (London: Adam Hilger, 1974).
  • R. M. Silverstein, C. Bassler, and T. C. Morill, Spectrometric Identification of Organic Compounds, 5th ed. (New York: John Wiley & Sons, 1991).
  • A. Parameswari, S. Premkumar, R. Premkumar, and A. Milton Franklin Benial, “Surface Enhanced Raman Spectroscopy and Quantum Chemical Studies on Glycine Single Crystal,” Journal of Molecular Structure 1116 (2016): 180–7. doi:10.1016/j.molstruc.2016.03.025
  • S. J. Koyambo-Konzapa, R. Premkumar, R. V. Berthelot Saïd Duvalier, M. K. Gilbert Yvon, M. Nsangou, and A. Milton Franklin Benial, “Electronic, Spectroscopic, Molecular Docking and Molecular Dynamics Studies of Neutral and Zwitterionic Forms of 3, 4-Dihydroxy-l-Phenylalanine: A Novel Lung Cancer Drug,” Journal of Molecular Structure 1260 (2022): 132844. doi:10.1016/j.molstruc.2022.132844
  • M. A. Albo Hay Allah, A. A. Balakit, H. I. Salman, A. A. Abdulridha, and Y. Sert, “New Heterocyclic Compound as Carbon Steel Corrosion Inhibitor in 1 M H2SO4, High Efficiency at Low Concentration: Experimental and Theoretical Studies,” Journal of Adhesion Science and Technology 37, no. 3 (2023): 525–47. doi:10.1080/01694243.2022.2034588
  • R. Geetha, M. R. Meera, C. Vijayakumar, R. Premkumar, and A. Milton Franklin Benial, “Synthesis, Spectroscopic Characterization, Molecular Docking and in Vitro Cytotoxicity Investigations on 8-Amino-6-Methoxy Quinolinium Picrate: A Novel Breast Cancer Drug,” Journal of Biomolecular Structure and Dynamics 41, no. 5 (2023): 1753–66. doi:10.1080/07391102.2021.2024259
  • R. Premkumar, S. Hussain, N. D. Jayram, S. J. Koyambo-Konzapa, M. S. Revathy, T. Mathavan, and A. Milton Franklin Benial, “Adsorption and Orientation Characteristics of 1-Methylpyrrole-2-Carbonyl Chloride Using SERS and DFT Investigations,” Journal of Molecular Structure 1253 (2022): 132201. doi:10.1016/j.molstruc.2021.132201
  • D. C. Ghosh, J. Jana, and R. Biswas, “Quantum Chemical Study of the Umbrella Inversion of the Ammonia Molecule,” International Journal of Quantum Chemistry 80, no. 1 (2000): 1–26. doi:10.1002/1097-461X(2000)80:1<1::AID-QUA1>3.0.CO;2-D
  • P. E. Smith, and B. M. Pettitt, “Effects of Salt on the Structure and Dynamics of the Bis(Penicillamine) Enkephalin Zwitterion: A Simulation Study,” Journal of the American Chemical Society 113, no. 16 (1991): 6029–37. doi:10.1021/ja00016a015
  • P. Cieplak, and P. Kollman, “On the Use of Electrostatic Potential Derived Charges in Molecular Mechanics Force Fields. The Relative Solvation Free Energy of Cis- and trans-N-Methyl-Acetamide,” Journal of Computational Chemistry 12, no. 10 (1991): 1232–6. doi:10.1002/jcc.540121010
  • R. G. Parr, L. V. Szentpaly, and S. Liu, “Electrophilicity Index,” Journal of the American Chemical Society 121, no. 9 (1999): 1922–4. doi:10.1021/ja983494x
  • T. Koopmans, “Uber Die Zuordnung Von Wellenfunktionen Und Eigenwerten ZuDen Einzelnen Elektronen Eines Atoms,” Physica 1, no. 1–6 (1934): 104–13. doi:10.1016/S0031-8914(34)90011-2
  • C. J. Cramer, Essentials of Computational Chemistry. (New York: Wiley, 2002).
  • Y. Megrouss, N. Benhalima, R. Bahoussi, N. Boukabcha, A. Chouaih, and A. Hamzaoui, “Determination of Electrostatic Parameters of a Coumarin Derivative Compound C17H13NO3 by x-Ray and Density Functional Theory,” Chinese Physics B 24, no. 10 (2015): 106103. doi:10.1088/1674-1056/24/10/106103
  • S. Hilton, S. Naud, J. J. Caldwell, K. Boxall, S. Burns, V. E. Anderson, L. Antoni, C. E. Allen, L. H. Pearl, A. W. Oliver, et al, “Identification and Characterisation of 2-Aminopyridine Inhibitors of Checkpoint Kinase 2,” Bioorganic & Medicinal Chemistry 18, no. 2 (2010): 707–18. doi:10.1016/j.bmc.2009.11.058
  • S. D. Kanmazalp, M. Macit, and N. Dege, “Hirshfeld Surface, Crystal Structure and “Spectroscopic Characterization of (E)-4-(Diethylamino)-2-((4-30 Phenoxyphenylimino)Methyl)Phenol with DFT Studies,” Journal of Molecular Structure 1179 (2019): 181–91. doi:10.1016/j.molstruc.2018.11.001
  • C. Çirak, and N. Koç, “Molecular Structure and Effects of Intermolecular Hydrogen Bonding on the Vibrational Spectrum of Trifluorothymine, an Antitumor and Antiviral Agent,” Journal of Molecular Modeling 18, no. 9 (2012): 4453–64. doi:10.1007/s00894-012-1449-5
  • A. E. Reed, L. A. Curtiss, and F. Weinhold, “Intermolecular Interactions from a Natural Bond Orbital, Donor-Acceptor Viewpoint,” Chemical Reviews 88, no. 6 (1988): 899–926. doi:10.1021/cr00088a005
  • Y. Wang, J. Ai, Y. Wang, Y. Chen, L. Wang, G. Liu, M. Geng, and A. Zhang, “Synthesis and cMet Kinase Inhibition of 3,5-Disubstituted and 3,5,7-Trisubstituted 29 Quinolines: Identification of 3-(4-Acetylpiperazin-1-yl)-5-(3-Nitrobenzylamino)-7- (Trifluoromethyl)Quinoline as a Novel Anticancer Agent,” Journal of Medicinal Chemistry 54, no. 7 (2011): 2127–42. doi:10.1021/jm101340q
  • M. Alcolea Palafox, S. M. Chalanchi, J. Isasi, R. Premkumar, A. Milton Franklin Benial, and V. K. Rastogi, “Effect of Bromine Atom on the Different Tautomeric Forms of Microhydrated 5-Bromouracil, in the DNA:RNA Microhelix and in the Interaction with Human Protein,” Journal of Biomolecular Structure & Dynamics 38, no. 18 (2020): 5443–63. doi:10.1080/07391102.2019.1704878
  • http://www.rcsb.org/pdb.

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