Pryazolylpyridine and Triazolylpyridine derivative of hydroxychloroquine as Potential Therapeutic against COVID-19: Theoretical Evaluation
Abstract
In attempt to improve the biological activity of the well-known drug hydroxychloroquine (HQC), eight derivatives (HQ1-4Py – HQ8-4Py) based on the core of HQC were design and their electronic properties including frontier molecular orbitals, total energy and structural parameters were estimated at semi-empirical PM3 levels. Pharmacological parameters such as physicochemical, pharmacokinetics, drug-likeness and medicinal chemistry friendliness have been evaluated to estimate the drugs similarity. Introducing these moieties affect both electronic and drug likeness properties, HQ5-Py shows promised properties such large Eg and good clogP, The obtained results show that the suggested derivates may represent a potential drug candidate for COVID-19.
Keywords: Molecular similarity, COVID-19, Hydroxychloroquine (HCQ).
Keywords:
Molecular similarity, COVID-19, Hydroxychloroquine (HCQ)., Molecular similarity
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References
[1] J. Gao, Z. Tian, and X. Yang, “Breakthrough: Chloroquine phosphate has shown apparent efficacy in treatment of COVID-19 associated pneumonia in clinical studies,” Biosci. Trends, 2020.
[2] Organization WH. Coronavirus disease (COVID-2019) situation reports. Geneva: WHO; 2020.
[3] Organization WH. Coronavirus disease (COVID-19) advice for the public. 2020.
[4] NIH U.S. National Library of Medicine. Available at: https://clinicaltrials.gov/. Accessed April 4 2020.
[5] A. H. J. Kim et al., “A Rush to Judgment? Rapid Reporting and Dissemination of Results and Its Consequences Regarding the Use of Hydroxychloroquine for COVID-19,” Ann. Intern. Med., 2020.
[6] I. Ben-Zvi, S. Kivity, P. Langevitz, and Y. Shoenfeld, “Hydroxychloroquine: From malaria to autoimmunity,” Clinical Reviews in Allergy and Immunology. 2012.
[7] X. Yao et al., “In Vitro Antiviral Activity and Projection of Optimized Dosing Design of Hydroxychloroquine for the Treatment of Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2),” Clin. Infect. Dis., 2020.
[8] K. A. Pastick et al., “Review : Hydroxychloroquine and Chloroquine for Treatment of SARS-CoV-2 ( COVID-19 ),” vol. 2, pp. 1–9, 2019.
[9] “Sanofi-Aventis U.S. LLC. Aralen Chloroquine Phosphate, USP, 2013.
[10] Concordia Pharmaceuticals Inc. Plaquenil Hydroxychloroquine Sulfate Tablets, USP, 2017.
[11] C. Biot et al., “Design and synthesis of hydroxyferroquine derivatives with antimalarial and antiviral activities,” J. Med. Chem., 2006.
[12] U.S. Food and Drug Administration. EUA Hydroxychloroquine sulfate Health Care Provider Fact Sheet March 28, 2020.
[13] J. P. T. Bultinck, Patrick, Winter, Hans DeWi If ried Langenaeker, Ed., Computational Medical Chemistry for Drug discovery. NEW YORK: Taylor & Francis Group LLC, 2004.
[14] K. V. Luna Parada LK, Vargas Méndez LY, “Quinoline-Substituted 1,2,3-Triazole-Based Molecules, As Promising Conjugated Hybrids in Biomedical Research.,” Org. Med. Chem IJ, vol. 7, no. 2, pp. 001–0010.
[15] J. Liu et al., “Hydroxychloroquine, a less toxic derivative of chloroquine, is effective in inhibiting SARS-CoV-2 infection in vitro,” Cell Discovery. 2020.
[16] W. F. Coleman and C. R. Arumainayagam, “HyperChem 5 (by Hypercube, Inc.),” J. Chem. Educ., 1998.
[17] A. Daina, O. Michielin, and V. Zoete, “SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules,” Sci. Rep., 2017.
[18] J. W. Steed, D. R. Turner, and K. J. Wallace, Core Concepts in Supramolecular Chemistry and Nanochemistry. 2007.
[19] D. L. Caulder and K. N. Raymond, “Supermolecules by Design,” Acc. Chem. Res., vol. 32, no. 11, pp. 975–982, Nov. 1999.
[20] A. Semeniuk, J. Kalinowska-Tluscik, W. Nitek, and B. J. Oleksyn, “Intermolecular Interactions in Crystalline Hydroxychloroquine Sulfate in Comparison with Those in Selected Antimalarial Drugs,” J. Chem. Crystallogr., vol. 38, no. 5, pp. 333–338, 2008.
[21] M. J. Islam, A. Zannat, A. Kumer, N. Sarker, and S. Paul, “The prediction and theoretical study for chemical reactivity, thermophysical and biological activity of morpholinium nitrate and nitrite ionic liquid crystals: A DFT study,” Adv. J. Chem. A, vol. 2, no. 4, pp. 316–326, 2019.
[22] M. J. Islam, N. Sarker, and A. Kumer, “The evaluation and comparison of thermo-physical, chemical and biological properties of palladium (II) complexes on binuclear diamine ligands with different anions using the DFT method,” Int. J. Adv. Biol. Biomed. Res., vol. 7, no. 4, pp. 315–334, 2019.
[23] S. Ekins, Computer Applications in Pharmaceutical Research and Development. 2006.
[24] C. A. Lipinski, F. Lombardo, B. W. Dominy, and P. J. Feeney, “Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings,” Advanced Drug Delivery Reviews. 1997.
[2] Organization WH. Coronavirus disease (COVID-2019) situation reports. Geneva: WHO; 2020.
[3] Organization WH. Coronavirus disease (COVID-19) advice for the public. 2020.
[4] NIH U.S. National Library of Medicine. Available at: https://clinicaltrials.gov/. Accessed April 4 2020.
[5] A. H. J. Kim et al., “A Rush to Judgment? Rapid Reporting and Dissemination of Results and Its Consequences Regarding the Use of Hydroxychloroquine for COVID-19,” Ann. Intern. Med., 2020.
[6] I. Ben-Zvi, S. Kivity, P. Langevitz, and Y. Shoenfeld, “Hydroxychloroquine: From malaria to autoimmunity,” Clinical Reviews in Allergy and Immunology. 2012.
[7] X. Yao et al., “In Vitro Antiviral Activity and Projection of Optimized Dosing Design of Hydroxychloroquine for the Treatment of Severe Acute Respiratory Syndrome Coronavirus 2 (SARS-CoV-2),” Clin. Infect. Dis., 2020.
[8] K. A. Pastick et al., “Review : Hydroxychloroquine and Chloroquine for Treatment of SARS-CoV-2 ( COVID-19 ),” vol. 2, pp. 1–9, 2019.
[9] “Sanofi-Aventis U.S. LLC. Aralen Chloroquine Phosphate, USP, 2013.
[10] Concordia Pharmaceuticals Inc. Plaquenil Hydroxychloroquine Sulfate Tablets, USP, 2017.
[11] C. Biot et al., “Design and synthesis of hydroxyferroquine derivatives with antimalarial and antiviral activities,” J. Med. Chem., 2006.
[12] U.S. Food and Drug Administration. EUA Hydroxychloroquine sulfate Health Care Provider Fact Sheet March 28, 2020.
[13] J. P. T. Bultinck, Patrick, Winter, Hans DeWi If ried Langenaeker, Ed., Computational Medical Chemistry for Drug discovery. NEW YORK: Taylor & Francis Group LLC, 2004.
[14] K. V. Luna Parada LK, Vargas Méndez LY, “Quinoline-Substituted 1,2,3-Triazole-Based Molecules, As Promising Conjugated Hybrids in Biomedical Research.,” Org. Med. Chem IJ, vol. 7, no. 2, pp. 001–0010.
[15] J. Liu et al., “Hydroxychloroquine, a less toxic derivative of chloroquine, is effective in inhibiting SARS-CoV-2 infection in vitro,” Cell Discovery. 2020.
[16] W. F. Coleman and C. R. Arumainayagam, “HyperChem 5 (by Hypercube, Inc.),” J. Chem. Educ., 1998.
[17] A. Daina, O. Michielin, and V. Zoete, “SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules,” Sci. Rep., 2017.
[18] J. W. Steed, D. R. Turner, and K. J. Wallace, Core Concepts in Supramolecular Chemistry and Nanochemistry. 2007.
[19] D. L. Caulder and K. N. Raymond, “Supermolecules by Design,” Acc. Chem. Res., vol. 32, no. 11, pp. 975–982, Nov. 1999.
[20] A. Semeniuk, J. Kalinowska-Tluscik, W. Nitek, and B. J. Oleksyn, “Intermolecular Interactions in Crystalline Hydroxychloroquine Sulfate in Comparison with Those in Selected Antimalarial Drugs,” J. Chem. Crystallogr., vol. 38, no. 5, pp. 333–338, 2008.
[21] M. J. Islam, A. Zannat, A. Kumer, N. Sarker, and S. Paul, “The prediction and theoretical study for chemical reactivity, thermophysical and biological activity of morpholinium nitrate and nitrite ionic liquid crystals: A DFT study,” Adv. J. Chem. A, vol. 2, no. 4, pp. 316–326, 2019.
[22] M. J. Islam, N. Sarker, and A. Kumer, “The evaluation and comparison of thermo-physical, chemical and biological properties of palladium (II) complexes on binuclear diamine ligands with different anions using the DFT method,” Int. J. Adv. Biol. Biomed. Res., vol. 7, no. 4, pp. 315–334, 2019.
[23] S. Ekins, Computer Applications in Pharmaceutical Research and Development. 2006.
[24] C. A. Lipinski, F. Lombardo, B. W. Dominy, and P. J. Feeney, “Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings,” Advanced Drug Delivery Reviews. 1997.
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1.
Omar R, Najar AM, Bobtaina E, Elsheikh AF. Pryazolylpyridine and Triazolylpyridine derivative of hydroxychloroquine as Potential Therapeutic against COVID-19: Theoretical Evaluation. JDDT [Internet]. 16Aug.2020 [cited 22Apr.2021];10(4-s):181-6. Available from: http://jddtonline.info/index.php/jddt/article/view/4298
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