278
Views
1
CrossRef citations to date
0
Altmetric
Research Articles

Structural, computational and in silico studies of 4-bromo-3-flurobenzonitrile as anti-Alzheimer and anti-Parkinson agents

, , , ORCID Icon &
Pages 4619-4643 | Received 29 Aug 2022, Accepted 29 May 2023, Published online: 07 Jul 2023

References

  • Advanced Organic Chemistry. (2002). Journal of Chemical Education, 79(Suppl). https://doi.org/10.1093/jaoac/34.2.496
  • Advances in Quantum Chemistry. (2013). Advances in Quantum Chemistry, 65(C). https://doi.org/10.1016/B978-0-12-396455-7.00017-0
  • Ahmed, M. N., Shabbir, S., Batool, B., Mahmood, T., Rashid, U., Yasin, K. A., Tahir, M. N., Cassará, M. L. A., & Gil, D. M. (2021). A new insight into non-covalent interactions in 1,4-disubstituted 1H-1,2,3-triazole: Synthesis, X-ray structure, DFT calculations, in vitro Lipoxygenase Inhibition (LOX) and in silico Studies. Journal of Molecular Structure, 1236, 130283. https://doi.org/10.1016/j.molstruc.2021.130283
  • Akyüz, D., Demirbaş, Ü., Koca, A., Çelik, F., & Kantekin, H. (2020). Electrochemistry, electropolymerization and electrochromism of novel phthalocyanines bearing morpholine groups. Journal of Molecular Structure, 1206, 127674. https://doi.org/10.1016/j.molstruc.2019.127674
  • Alaminsky, R. J., & Seminario, J. M. (2019). Sigma-holes from iso-molecular electrostatic potential surfaces. Journal of Molecular Modeling, 25(6). https://doi.org/10.1007/s00894-019-4051-2
  • Alkorta, I., & Perez, J. J. (1996). Molecular polarization potential maps of the nucleic acid bases. International Journal of Quantum Chemistry, 57(1), 123–135. https://doi.org/10.1002/(SICI)1097-461X(1996)57:1<123::AID-QUA14>3.0.CO;2-9
  • Almaz, Z., Oztekin, A., Tan, A., & Ozdemir, H. (2021). Biological evaluation and molecular docking studies of 4-aminobenzohydrazide derivatives as cholinesterase inhibitors. Journal of Molecular Structure, 1244, 130918. https://doi.org/10.1016/j.molstruc.2021.130918
  • Andrea, V., & Ho, P. H. (2007). The role of halogen bonding in inhibitor recognition and binding by protein kinases. Current Topics in Medicinal Chemistry, 7(14), 1336–1348. https://doi.org/10.2174/156802607781696846
  • Andrés, J., Berski, S., Contreras-García, J., & González-Navarrete, P. (2014). Following the molecular mechanism for the NH3 + LiH → LiNH2 + H2 chemical reaction: A study based on the joint use of the quantum theory of atoms in molecules (QTAIM) and noncovalent interaction (NCI) index. The Journal of Physical Chemistry A, 118(9), 1663–1672. https://doi.org/10.1021/jp4111376
  • Auffinger, P., Hays, F. A., Westhof, E., & Ho, P. S. (2004). Halogen bonds in biological molecules. Proceedings of the National Academy of Sciences USA, 101(48), 16789–16794. https://doi.org/10.1073/pnas.0407607101
  • Azam, F., Abodabos, H. S., Taban, I. M., Rfieda, A. R., Mahmood, D., Anwar, M. J., Khan, S., Sizochenko, N., Poli, G., Tuccinardi, T., & Ali, H. I. (2019). Rutin as promising drug for the treatment of Parkinson’s disease: An assessment of MAO-B inhibitory potential by docking, molecular dynamics and DFT studies. Molecular Simulation, 45(18), 1563–1571. https://doi.org/10.1080/08927022.2019.1662003
  • Azhar, E. I., Hindawi, S. I., El-Kafrawy, S. A., Hassan, A. M., Tolah, A. M., Alandijany, T. A., Bajrai, L. H., & Damanhouri, G. A. (2021). Amotosalen and ultraviolet A light treatment efficiently inactivates severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in human plasma. Vox Sanguinis, 116(6), 673–681. https://doi.org/10.1111/vox.13043
  • Balachandran, V., Lakshmi, A., & Janaki, A. (2012). Conformational stability, vibrational spectral studies, HOMO-LUMO and NBO analyses of 2-hydroxy-4-methyl-3-nitropyridine and 2-hydroxy-4-methyl-5- nitropyridine based on density functional theory. Journal of Molecular Structure, 1013, 75–85. https://doi.org/10.1016/j.molstruc.2012.01.021
  • Bharadwaj, S., El-Kafrawy, S. A., Alandijany, T. A., Bajrai, L. H., Shah, A. A., Dubey, A., Sahoo, A. K., Yadava, U., Kamal, M. A., Azhar, E. I., Kang, S. G., & Dwivedi, V. D. (2021). Structure-based identification of natural products as sars-cov-2 mpro antagonist from echinacea angustifolia using computational approaches. Viruses, 13(2), 305. https://doi.org/10.3390/v13020305
  • Bissantz, C., Kuhn, B., & Stahl, M. (2010). Corrections to a medicinal chemist’s guide to molecular interactions. Journal of Medicinal Chemistry, 53(16), 6241–6241. https://doi.org/10.1021/jm100950p
  • Chang, C., Lang, H., Geng, N., Wang, J., Li, N., & Wang, X. (2013). Exosomes of BV-2 cells induced by alpha-synuclein: Important mediator of neurodegeneration in PD. Neuroscience Letters, 548, 190–195. https://doi.org/10.1016/j.neulet.2013.06.009
  • Chethan, B. S., & Lokanath, N. K. (2022). Study of the crystal structure, H-bonding and noncovalent interactions of novel cocrystal by systematic computational search approach. Journal of Molecular Structure, 1251, 131936. https://doi.org/10.1016/j.molstruc.2021.131936
  • Chethan Prathap, K. N., & Lokanath, N. K. (2018). Synthesis, characterization, crystal structure and quantum chemical investigations of three novel coumarin-benzenesulfonohydrazide derivatives. Journal of Molecular Structure, 1158, 26–38. https://doi.org/10.1016/j.molstruc.2018.01.007
  • Clark, T., Hennemann, M., Murray, J. S., & Politzer, P. (2007). Halogen bonding: The σ-hole. Journal of Molecular Modeling, 13(2), 291–296. https://doi.org/10.1007/s00894-006-0130-2
  • Contreras-García, J., Johnson, E. R., Keinan, S., Chaudret, R., Piquemal, J. P., Beratan, D. N., & Yang, W. (2011). NCIPLOT: A program for plotting noncovalent interaction regions. Journal of Chemical Theory and Computation, 7(3), 625–632. https://doi.org/10.1021/ct100641a
  • D. E. Shaw Research. (2019). Desmond molecular dynamics system. Schrödinger Release.
  • Daina, A., Michielin, O., & Zoete, V. (2017). SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Scientific Reports, 427177. https://doi.org/10.1038/srep42717
  • Deb, B., Debnath, S., Chakraborty, A., & Majumdar, S. (2021). Bis-indolylation of aldehydes and ketones using silica-supported FeCl3: Molecular docking studies of bisindoles by targeting SARS-CoV-2 main protease binding sites. RSC Advances, 11(49), 30827–30839. https://doi.org/10.1039/D1RA05679D
  • Dennington, R., Keith, T. A., & Millam, J. M. (2016). GaussView 6. Gaussian.
  • Dumas, J. A., & Newhouse, P. A. (2011). The cholinergic hypothesis of cognitive aging revisited again: Cholinergic functional compensation. Pharmacology Biochemistry and Behavior, 99 (2), 254–261. https://doi.org/10.1016/j.pbb.2011.02.022
  • Elengoe, A., & Loganthan, V. (2022). Molecular modeling and docking studies on phyto-compounds against caspase-3, brca1, and rb. Biointerface Research in Applied Chemistry, 12(6). https://doi.org/10.33263/BRIAC126.76067620
  • Farrugia, L. J. (1997). ORTEP-3 for windows – A version of ORTEP-III with a graphical user interface (GUI). Journal of Applied Crystallography, 30(5), 565–565. https://doi.org/10.1107/S0021889897003117
  • Fazilath Basha, A., Liakath Ali Khan, F., Muthu, S., & Raja, M. (2021). Computational evaluation on molecular structure (Monomer, Dimer), RDG, ELF, electronic (HOMO-LUMO, MEP) properties, and spectroscopic profiling of 8-quinolinesulfonamide with molecular docking studies. Computational and Theoretical Chemistry, 1198, 113169. https://doi.org/10.1016/j.comptc.2021.113169
  • Ferreira, J. P. S., Albuquerque, H. M. T., Cardoso, S. M., Silva, A. M. S., & Silva, V. L. M. (2021). Dual-target compounds for Alzheimer’s disease: Natural and synthetic AChE and BACE-1 dual-inhibitors and their structure-activity relationship (SAR). European Journal of Medicinal Chemistry, 221, 113492. https://doi.org/10.1016/j.ejmech.2021.113492
  • Foster, J. P., & Weinhold, F. (1980). Natural hybrid orbitals. Journal of the American Chemical Society, 102(24), 7211–7218. https://doi.org/10.1021/ja00544a007
  • Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Petersson, G. A., & Nakatsuji, H. (2016). Gaussian 16 revision a. 03. 2016; gaussian inc. Wallingford CT. 2(3).
  • Fritzsche, H. (2010). Vibrational spectra of benzene derivatives: Von G. Varsányi. Akadémiai Kiadó, Budapest. 1969, 430 Seiten mit zahlreichen Bildern und Tabellen, Format 16,5 × 23 cm, Ln. Zeitschrift für Chemie, 10(6), 238–238. https://doi.org/10.1002/zfch.19700100626
  • Gong, J., Lam, J. W. Y., & Tang, B. Z. (2020). Benchmark and parameter tuning of hybrid functionals for fast calculation of excitation energies of AIEgens. Physical Chemistry Chemical Physics, 22(32), 18035–18039. https://doi.org/10.1039/D0CP02704A
  • Govindarajan, M., Karabacak, M., Suvitha, A., & Periandy, S. (2012). FT-IR, FT-Raman, ab initio, HF and DFT studies, NBO, HOMO-LUMO and electronic structure calculations on 4-chloro-3-nitrotoluene. Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 89. https://doi.org/10.1016/j.saa.2011.12.067
  • Greig, N. H., Lahiri, D. K., & Sambamurti, K. (2002). Butyrylcholinesterase: An important new target in Alzheimer’s disease therapy. International Psychogeriatrics, 14(S1), 77–91. https://doi.org/10.1017/S1041610203008676
  • Hardy, J., & Allsop, D. (1991). Amyloid deposition as the central event in the aetiology of Alzheimer’s disease. Trends in Pharmacological Sciences , 12, 383–388. https://doi.org/10.1016/0165-6147(91)90609-V
  • Humphrey, W., Dalke, A., & Schulten, K. (1996). VMD: Visual molecular dynamics. Journal of Molecular Graphics, 14(1), 33–38. https://doi.org/10.1016/0263-7855(96)00018-5
  • Ibrahim, M. A. A. (2011). Molecular mechanical study of halogen bonding in drug discovery. Journal of Computational Chemistry, 32(12), 2564–2574. https://doi.org/10.1002/jcc.21836
  • Jain, A. N. (1996). Scoring noncovalent protein–ligand interactions: A continuous differentiable function tuned to compute binding affinities. Journal of Computer-Aided Molecular Design, 10(5), 427–440. https://doi.org/10.1007/BF00124474
  • Kalirajan, R., Pandiselvi, A., Gowramma, B., & Balachandran, P. (2019). In-silico design, ADMET screening, MM-GBSA binding free energy of some novel isoxazole substituted 9-anilinoacridines as HER2 inhibitors targeting breast cancer. Current Drug Research Reviews, 11(2), 118–128. https://doi.org/10.2174/2589977511666190912154817
  • Koohi, M., & Bastami, H. (2020). Substituent effects on stability, MEP, NBO analysis, and reactivity of 2,2,9,9-tetrahalosilacyclonona-3,5,7-trienylidenes, at density functional theory. Monatshefte Für Chemie – Chemical Monthly, 151(1), 11–23. https://doi.org/10.1007/s00706-019-02537-w
  • Kumar, A., Pintus, F., di Petrillo, A., Medda, R., Caria, P., Matos, M. J., Viña, D., Pieroni, E., Delogu, F., Era, B., Delogu, G. L., & Fais, A. (2018). Novel 2-pheynlbenzofuran derivatives as selective butyrylcholinesterase inhibitors for Alzheimer’s disease. Scientific Reports, 8(1). https://doi.org/10.1038/s41598-018-22747-2
  • Kurt, M., Babu, P. C., Sundaraganesan, N., Cinar, M., & Karabacak, M. (2011). Molecular structure, vibrational, UV and NBO analysis of 4-chloro-7-nitrobenzofurazan by DFT calculations. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 79(5), 1162–1170. https://doi.org/10.1016/j.saa.2011.04.037
  • Lavoie, C. M., Tassone, J. P., Ferguson, M. J., Zhou, Y., Johnson, E. R., & Stradiotto, M. (2018). Probing the influence of PAd-DalPhos ancillary ligand structure on nickel-catalyzed ammonia cross-coupling. Organometallics, 37(21), 4015–4023. https://doi.org/10.1021/acs.organomet.8b00605
  • Liu, Y. M., Feng, Y. D., Lu, X., Nie, J. B., Li, W., Wang, L. N., Tian, L. J., & Liu, Q. H. (2017). Isosteroidal alkaloids as potent dual-binding site inhibitors of both acetylcholinesterase and butyrylcholinesterase from the bulbs of Fritillaria walujewii. European Journal of Medicinal Chemistry, 137, 280–291. https://doi.org/10.1016/j.ejmech.2017.06.007
  • Lu, T., & Chen, F. (2012). Multiwfn: A multifunctional wavefunction analyzer. Journal of Computational Chemistry, 33(5), 580–592. https://doi.org/10.1002/jcc.22885
  • Luque, F. J., Orozco, M., Bhadane, P. K., & Gadre, S. R. (1993). SCRF calculation of the effect of hydration on the topology of the molecular electrostatic potential. Journal of Physical Chemistry, 97(37). https://doi.org/10.1021/j100139a021
  • Mackenzie, C. F., Spackman, P. R., Jayatilaka, D., & Spackman, M. A. (2017). CrystalExplorer model energies and energy frameworks: Extension to metal coordination compounds, organic salts, solvates and open-shell systems. IUCrJ, 4(5), 575–587. https://doi.org/10.1107/S205225251700848X
  • Metrangolo, P., Meyer, F., Pilati, T., Resnati, G., & Terraneo, G. (2008). Halogen bonding in supramolecular chemistry. Angewandte Angewandte Chemie International Edition , 47 (33), 6114–6127. https://doi.org/10.1002/anie.200800128
  • Mohammad, R. K., Jassim, S., & Ahmed, L. (2021). Halogens substitution effects on electronic and spectral properties of carbon nanotube molecules studying with the DFT method. Egyptian Journal of Chemistry. https://doi.org/10.21608/ejchem.2021.74728.3680
  • Morris, G. M., Goodsell, D. S., Halliday, R. S., Huey, R., Hart, W. E., Belew, R. K., & Olson, A. J. (1998). Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. Journal of Computational Chemistry, 19(14), 1639–1662. https://doi.org/10.1002/(SICI)1096-987X(19981115)19:14<1639::AID-JCC10>3.0.CO;2-B
  • Morris, G. M., Ruth, H., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., & Olson, A. J. (2009). Software news and updates AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry, 30(16), 2785–2791. https://doi.org/10.1002/jcc.21256
  • Noorizadeh, S., & Shakerzadeh, E. (2010). Shannon entropy as a new measure of aromaticity, Shannon aromaticity. Physical Chemistry Chemical Physics, 12(18), 4742. https://doi.org/10.1039/b916509f
  • Öztaskın, N., Taslimi, P., Maraş, A., Gülcin, İ., & Göksu, S. (2017). Novel antioxidant bromophenols with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions. Bioorganic Chemistry, 74, 104–114. https://doi.org/10.1016/j.bioorg.2017.07.010
  • Patani, G. A., & LaVoie, E. J. (1996). Bioisosterism: A rational approach in drug design. Chemical Reviews, 96(8), 3147–3176. https://doi.org/10.1021/cr950066q
  • Patel, M. K., Patel, U. H., Gandhi, S. A., Barot, V. M., & Jayswal, J. (2019). Solvent effect on neutral Co (II) complexes of paeonol derivative –qualitative and quantitative studies from energy frame work and Hirshfeld surface analysis. Journal of Molecular Structure, 1196, 119–131. https://doi.org/10.1016/j.molstruc.2019.06.050
  • Pattar, S. V., Adhoni, S. A., Kamanavalli, C. M., & Kumbar, S. S. (2020). In silico molecular docking studies and MM/GBSA analysis of coumarin-carbonodithioate hybrid derivatives divulge the anticancer potential against breast cancer. Beni-Suef University Journal of Basic and Applied Sciences, 9(1). https://doi.org/10.1186/s43088-020-00059-7
  • Piggot, T. J., Holdbrook, D. A., & Khalid, S. (2013). Conformational dynamics and membrane interactions of the E. coli outer membrane protein FecA: A molecular dynamics simulation study. Biochimica et Biophysica Acta (BBA) – Biomembranes, 1828(2), 284–293. https://doi.org/10.1016/j.bbamem.2012.08.021
  • Pires, D. E. V., Blundell, T. L., & Ascher, D. B. (2015). pkCSM: Predicting small-molecule pharmacokinetic and toxicity properties using graph-based signatures. Journal of Medicinal Chemistry, 58(9), 4066–4072. https://doi.org/10.1021/acs.jmedchem.5b00104
  • Politzer, P., Lane, P., Concha, M. C., Ma, Y., & Murray, J. S. (2007). An overview of halogen bonding. Journal of Molecular Modeling, 13(2), 305–311. https://doi.org/10.1007/s00894-006-0154-7
  • Politzer, P., & Murray, J. S. (2018). σ-Holes and π-holes: Similarities and differences. Journal of Computational Chemistry, 39(9), 464–471. https://doi.org/10.1002/jcc.24891
  • Pourabdi, L., Küçükkılınç, T. T., Khoshtale, F., Ayazgök, B., Nadri, H., Farokhi Alashti, F., Forootanfar, H., Akbari, T., Shafiei, M., Foroumadi, A., Sharifzadeh, M., Shafiee Ardestani, M., Abaee, M. S., Firoozpour, L., Khoobi, M., & Mojtahedi, M. M. (2021). Synthesis of new 3-arylcoumarins bearing N-benzyl triazole moiety: Dual lipoxygenase and butyrylcholinesterase inhibitors with anti-amyloid aggregation and neuroprotective properties against Alzheimer’s disease. Frontiers in Chemistry, 9, 810233. https://doi.org/10.3389/fchem.2021.810233
  • Reed, A. E., Curtiss, L. A., & Weinhold, F. (1988). Intermolecular interactions from a natural bond orbital, donor—Acceptor viewpoint. Chemical Reviews, 88(6), 899–926. https://doi.org/10.1021/cr00088a005
  • Rosenberg, G. A. (2009). Matrix metalloproteinases and their multiple roles in neurodegenerative diseases. The Lancet Neurology, 8(2), 205–216. https://doi.org/10.1016/S1474-4422(09)70016-X
  • Salzner, U., & Aydin, A. (2011). Improved prediction of properties of π-conjugated oligomers with range-separated hybrid density functionals. Journal of Chemical Theory and Computation, 7(8), 2568–2583. https://doi.org/10.1021/ct2003447
  • Sethi, A., & Prakash, R. (2015). Novel synthetic ester of Brassicasterol, DFT investigation including NBO, NLO response, reactivity descriptor and its intramolecular interactions analyzed by AIM theory. Journal of Molecular Structure, 1083, 72–81. https://doi.org/10.1016/j.molstruc.2014.11.028
  • Shaikh, S., Dhavan, P., Singh, P., Uparkar, J., Vaidya, S. P., Jadhav, B. L., & Ramana, M. v. (2022). Synthesis of carbazole based α-aminophosphonate derivatives: Design, molecular docking and in vitro cholinesterase activity. Journal of Biomolecular Structure and Dynamics, 40(11), 4801–4814. https://doi.org/10.1080/07391102.2020.1861981
  • Sheldrick, G. M. (2008). A short history of SHELX. In Acta Crystallographica Section A: Foundations of Crystallography, 64(1). https://doi.org/10.1107/S0108767307043930
  • Sheldrick, G. M. (2015). Crystal structure refinement with SHELXL. Crystal Structure Refinement: A Crystallographer’s Guide to SHELXL, 71(1), 3-8. https://doi.org/10.1107/S2053229614024218.
  • Shi, M. W., Thomas, S. P., Koutsantonis, G. A., & Spackman, M. A. (2015). Supramolecular recognition and energy frameworks in host-guest complexes of 18-crown-6 and sulfonamides. Crystal Growth & Design, 15(12), 5892–5900. https://doi.org/10.1021/acs.cgd.5b01316
  • Shing Ho, P. (2014). Biomolecular halogen bonds. Topics in Current Chemistry, 358. https://doi.org/10.1007/128_2014_551
  • Shit, S., Marschner, C., & Mitra, S. (2016). Synthesis, crystal structure, and hirshfeld surface analysis of a new mixed ligand copper(II) complex. Acta Chimica Slovenica, 63(1), 129–137. https://doi.org/10.17344/acsi.2015.2024
  • Shivakumar, D., Harder, E., Damm, W., Friesner, R. A., & Sherman, W. (2012). Improving the prediction of absolute solvation free energies using the next generation opls force field. Journal of Chemical Theory and Computation, 8(8), 2553–2558. https://doi.org/10.1021/ct300203w
  • Spackman, M. A., & McKinnon, J. J. (2002). Fingerprinting intermolecular interactions in molecular crystals. CrystEngComm, 4(66), 378–392. https://doi.org/10.1039/B203191B
  • Spackman, P. R., Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Jayatilaka, D., & Spackman, M. A. (2021). CrystalExplorer: A program for Hirshfeld surface analysis, visualization and quantitative analysis of molecular crystals. Journal of Applied Crystallography, 54(3), 1006–1011. https://doi.org/10.1107/S1600576721002910
  • Stone, A. J. (2008). Intermolecular potentials. Science (New York, N.Y.), 321(5890), 787–789. https://doi.org/10.1126/science.1158006
  • Strom, R. G., & Neukum, G. (2021). The cratering record on mercury and the origin of impacting objects. Mercury. https://doi.org/10.2307/j.ctv1v090nx
  • Biovia, D. S. (2017). Discovery studio visualizer. San Diego, CA, USA, 936.
  • Sun, H., Li, Y., Tian, S., Xu, L., & Hou, T. (2014). Assessing the performance of MM/PBSA and MM/GBSA methods. 4. Accuracies of MM/PBSA and MM/GBSA methodologies evaluated by various simulation protocols using PDBbind data set. Physical Chemistry Chemical Physics, 16(31), 16719–16729. https://doi.org/10.1039/C4CP01388C
  • Thiratmatrakul, S., Yenjai, C., Waiwut, P., Vajragupta, O., Reubroycharoen, P., Tohda, M., & Boonyarat, C. (2014). Synthesis, biological evaluation and molecular modeling study of novel tacrine-carbazole hybrids as potential multifunctional agents for the treatment of Alzheimer’s disease. European Journal of Medicinal Chemistry, 75, 21–30. https://doi.org/10.1016/j.ejmech.2014.01.020
  • Thompson, H. W., & Torkington, P. (1945). The vibrational spectra of esters and ketones. Journal of the Chemical Society (Resumed), 640. https://doi.org/10.1039/jr9450000640
  • Tso, C. J., Kasai, T., & Lin, K. C. (2020). Roaming dynamics and conformational memory in photolysis of formic acid at 193 nm using time-resolved fourier-transform infrared emission spectroscopy. Scientific Reports, 10(1). https://doi.org/10.1038/s41598-020-61642-7
  • Tsui, V., & Case, D. A. (2000). Theory and applications of the generalized born solvation model in macromolecular simulations. Biopolymers, 56(4), 275–291. https://doi.org/10.1002/1097-0282(2000)56:4<275::AID-BIP10024>3.0.CO;2-E
  • Turner, M. J., Thomas, S. P., Shi, M. W., Jayatilaka, D., & Spackman, M. A. (2015). Energy frameworks: Insights into interaction anisotropy and the mechanical properties of molecular crystals. Chemical Communications, 51(18), 3735–3738. https://doi.org/10.1039/C4CC09074H
  • Uchida, T., Takeya, S., Wilson, L. D., Tulk, C. A., Ripmeester, J. A., Nagao, J., Ebinuma, T., & Narita, H. (2003). Measurements of physical properties of gas hydrates and in situ observations of formation and decomposition processes via Raman spectroscopy and X-ray diffraction. Canadian Journal of Physics, 81(1–2), 351–357. https://doi.org/10.1139/p03-017
  • Wang, D. F., Helquist, P., Wiech, N. L., & Wiest, O. (2005). Toward selective histone deacetylase inhibitor design: Homology modeling, docking studies, and molecular dynamics simulations of human class I histone deacetylases. Journal of Medicinal Chemistry, 48(22), 6936–6947. https://doi.org/10.1021/jm0505011
  • Weinhold, F., & Landis, C. R. (2005). Valency and bonding: A natural bond orbital donor–acceptor perspective. Valency and Bonding: A Natural Bond Orbital Donor-Acceptor Perspective. https://doi.org/10.1017/CBO9780511614569
  • Williams, D. H., Stephens, E., O'Brien, D. P., & Zhou, M. (2004). Understanding noncovalent interactions: Ligand binding energy and catalytic efficiency from ligand-induced reductions in motion within receptors and enzymes. Angewandte Chemie (International ed. In English), 43(48), 6596–6616. https://doi.org/10.1002/anie.200300644
  • Xu, Z., Zhang, Q., Shi, J., & Zhu, W. (2019). Underestimated noncovalent interactions in Protein Data Bank. Journal of Chemical Information and Modeling, 59(8), 3389–3399. https://doi.org/10.1021/acs.jcim.9b00258
  • Zhou, P., Tian, F., Zou, J., & Shang, Z. (2010). Rediscovery of halogen bonds in protein–ligand complexes. Mini-Reviews in Medicinal Chemistry, 10(4), 309–314. https://doi.org/10.2174/138955710791331016
  • Zienkiewicz, O. C., Taylor, R. L., Zienckiewicz, Taylor, Ziaie-Moayed, R., Kamalzare, M., Safavian, M., Zhou, S.-J., Zhou, H., Wen, X., Zhang, Z. Z. M., Huang, C. L., Zhang, Z. Z. M., Zhang, X., Li, L., Chen, L. Z. L., Zhang, Q. Q., Zhang, Z. Z. M., He, J. Y, … (Ufc), U. F. C. (2013). Numerical study of floating stone (static). Computers and Geotechnics, 2(2).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.