JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 63 No 4 (2018): Journal of the Chilean Chemical Society
Original Research Papers

THEORETICAL ANALYSIS OF THE RELATIONSHIP BETWEEN THE ELECTRONIC STRUCTURE AND ITS INHIBITORY ACTION IN THE P2X7R RECEPTOR OF A SERIES OF 2-HYDROXY-1,4-NAPHTHOQUINONES DERIVATIVES

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  • Carlos Soloaga Ardiles,
  • José Cárcamo Vega
Carlos Soloaga Ardiles
Departamento de Química, Universidad de Tarapacá
José Cárcamo Vega
Laboratorio de Análisis e Investigaciones Arqueométricas (LAIA), Instituto de Alta Investigación (IAI), Universidad de Tarapacá
Published January 9, 2019
Keywords
  • P2X7R receptor,
  • 2-hydoxy-1,
  • 4-naphthaquinones derivatives,
  • KPG method (QSAR)
How to Cite
Soloaga Ardiles, C., & Cárcamo Vega, J. (2019). THEORETICAL ANALYSIS OF THE RELATIONSHIP BETWEEN THE ELECTRONIC STRUCTURE AND ITS INHIBITORY ACTION IN THE P2X7R RECEPTOR OF A SERIES OF 2-HYDROXY-1,4-NAPHTHOQUINONES DERIVATIVES. Journal of the Chilean Chemical Society, 63(4). Retrieved from https://www.jcchems.com/index.php/JCCHEMS/article/view/917

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Abstract

In this work, a theoretical study of the relationship between the electronic structure and the activity of the P2X7R receptor from 2-hydroxy-1,4-naphthoqui­none derivatives, using the KPG method, was performed. The electronic structure of the molecules was calculated at level B3LYP / 6-31G (d, p) with full geometry optimization. A statistically significant equation was obtained by relating the variation of biological activity with the variation of a set of indices of local atomic reactivity. Based on the analysis of the results, a two-dimensional pharmacophore was proposed.

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References

  1. Arulkumaran, N., R.J. Unwin, and F.W. Tam, A potential therapeutic role for P2X7 receptor (P2X7R) antagonists in the treatment of inflammatory diseases. Expert opinion on investigational drugs. Taylor & Franci.; 20, 897, (2011).
  2. Baggio, S.L.E., The P2X7 receptor in inflammatory diseases: Angel or demon? Front Pharmacol. 9, 52, (2018).
  3. Franchi, L., et al., Differential requirement of P2X7 receptor and intracel¬lular K+ for caspase-1 activation induced by intracellular and extracellular bacteria. J. Bio. Chem., ASBMB. 282, 18810, (2007).
  4. Burnstock, G. and G.E. Knight, The potential of P2X7 receptors as a thera¬peutic target, including inflammation and tumour progression Purinergic signalling. S Springer. 14, 18, (2018).
  5. Di Virgilio, F., et al., Non-nucleotide agonists triggering P2X7 receptor activation and pore formation. Front. Pharmaco., Frontiers. 9, 39, (2018).
  6. Safya, H., et al., Variations in Cellular Responses of Mouse T Cells to Adenosine-5′-Triphosphate Stimulation Do Not Depend on P2X7 Recep¬tor Expression Levels but on Their Activation and Differentiation Stage. Front. Immun., Frontiers.; 9, 360, (2018).
  7. Di Virgilio, F., G. Schmalzing, and F. Markwardt, The elusive P2X7 mac¬ropore. T Tren. Cell. Bio., Elsevier. 28, 392, (2018).
  8. Burnstock, G., Purinergic signalling: therapeutic developments Frontiers in pharmacology. Frontiers.; 8, 661, (2017).
  9. Zhang, W., et al., miR-373 regulates inflammatory cytokine-mediated chondrocyte proliferation in osteoarthritis by targeting the P2X7 receptor. FEBS Open Bio, Wiley Online Library. 8, 325, (2018).
  10. Ou, A., B.J. Gu, and J.S. Wiley, The scavenger activity of the human P2X7 receptor differs from P2X7 pore function by insensitivity to antagonists, genetic variation and sodium concentration. Relevance to inflammatory brain diseases Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, Elsevier. 1864, 1051, (2018).
  11. Zhou, Y., et al., Infection, Genetics and Evolution. Elsevier. 57, 138, (2018).
  12. Wei, L., et al., ATP-activated P2X7 receptor in the pathophysiology of mood disorders and as an emerging target for the development of novel an¬tidepressant therapeutics. Neurosci Biobehav R, Elsevier. 87, 192 (2018).
  13. Faria, R., et al., 1, 4-Naphthoquinones potently inhibiting P2X7 receptor activity. Eur J Med Chem.143, 1361, (2 018).
  14. Leyva, E., et al., Importancia quimica y biológica de naftoquinonas. evisión bibliográfica. Afinidad.; 74 (2017).
  15. Wiley, J., et al., The human P2X7 receptor and its role in innate immunity. HLA. 78, 321, (2011).
  16. Liu, C.S., G.-N.; Luo, Y.-H.; Piao, X.-J.; Jiang, X.-Y.; Meng, L.-Q.; Wang, Y.; Zhang, Y.; Wang, J.-R.; Wang, Novel 1, 4-Naphthoquinone de¬rivatives induce apoptosis via ROS-mediated p38/MAPK, Akt and STAT3 signaling in human hepatoma Hep3B cells Article (liu2018novel) Liu, C.; Shen, G.-N.; Luo, Y.-H.; Piao, X.-J.; Jiang, X.-Y.; Meng, L.-Q.; Wang, Y.; Zhang, Y.; Wang, J.-R.; Wang, H. & others Novel 1, 4-Naphthoqui¬none derivatives induce apoptosis via ROS-mediated p38/MAPK, Akt and STAT3 signaling in human hepatoma Hep3B cells. The international J. Biochem. & cell biology, Elsevier, (2018).
  17. Sandur, S.K., et al., Plumbagin (5-hydroxy-2-methyl-1, 4-naphthoqui¬none) suppresses NF-κB activation and NF-κB-regulated gene products through modulation of p65 and IκBα kinase activation, leading to potentia¬tion of apoptosis induced by cytokine and chemotherapeutic agents. J. Bio. Chem.,. 281, 7023, (2006).
  18. Lara, L.M., C.; Calvet, C.; Lechuga, G.; Souza, R.; Bourguignon, S.; Fer¬reira, V.; Rocha, D. & Pereira, M, Efficacy of 2-hydroxy-3-phenylsulfa¬nylmethyl-[1, 4]-naphthoquinone derivatives against different Trypano¬soma cruzi discrete type units: Identification of a promising hit compound. European J Med. Chem., Elsevier, 144, 572, (2018).
  19. Bao, N.O., J. Shi, W. Li, N. Chen, L. Sun, J., Highly Efficient Synthesis and Structure--Activity Relationships of a Small Library of Substituted 1, 4-Naphthoquinones. Eur J Med Chem, Wiley Online Library, 2018, 2254, (2018).
  20. Alarcón, D., F. Gatica-Díaz, and J.S. Gómez-Jeria, Modeling the rela¬tionships between molecular structure and inhibition of virus-induced cytophatic effects. Anti-HIV and anti-H1N1 (Influenza) activities as ex¬amples. J. Chil. Chem. Soc, 2013.
  21. Barahona, C.N., S. Gómez, J, Model-basedquantum-chemical study of the uptake of some polychlorinated pollutant compounds by Zucchini subspe¬cies. J. C. Chem. Soc, , 57, 1497, (2012).
  22. Lozano-Aponte, J. and T. Scior, ¿Qué sabe Ud. acerca de... QSAR? Re¬vista mexicana de ciencias farmacéuticas. 43, 82, (2012).
  23. Gómez, J., D. Alarcón, and A. Paz de la Vega, Quantum chemical study of the relationships between electronic structure and pharmacokinetic profile, inhibitory strength toward hepatitis c virus ns5b polymerase and hcv repli¬cons of indole-based compounds. J. C. Chem. Soc. 58, 1842, (2013).
  24. Hudson, R. and G. Klopman, A general perturbation treatment of chemical reactivity. Tetrahedron Letters. 8; 1103, (1967).
  25. Kooyman, E.C. and J.W. Heringa, Extension of the K-Region Hypothesis of Carcinogenic Chemical. Compounds. Nature, 170, 661, (1952).
  26. Gómez-Jeria, J.S., A new set of local reactivity indices within the Hartree- Fock-Roothaan and density functional theory. Can. Chem. Trans. 1, 25, (2013).
  27. Peradejordi, F., A.N. Martin, and A. Cammarata, Quantum chemical ap¬proach to structure-activity relationships of tetracycline antibiotics. J. Pharm. Sci. 60, 576, (1971).
  28. Roothaan, C.C., New Developments in Molecular Orbital Theory. Rev. Mod. Phys. 23, 69, (1951).
  29. De La Vega A, P., D.A. Alarcon, and J.S. Gómez Jeria, Quantum chemical study of the relationships between electronic structure and pharmacoki¬netic profile, inhibitory strength toward hepatitis c virus ns5b polymerase and hcv replicons. J. C. Chem. Soc.. 58, 2157, (2013).
  30. Zerner, M., Perspective on “New developments in molecular orbital theo¬ry”. Theor. Chem. Acc.. 103, 217, (2000).
  31. Gomez-Jeria, J.S., On some problems in quantum pharmacology I. The partition functions. International journal of quantum chemistry, Wiley On¬line Library. 23, 1969, (1983).
  32. Karelson, M., V. Lobanov, and A. Katritzky, Quantum-chemical descrip¬tors in QSAR/QSPR studies. Chemical reviews. 96, 1027, (1996).
  33. Gómez, S.S., Francisco, A Theoretical Study of the Relationships between Electronic Structure and CB1 and CB2 Cannabinoid Receptor Binding Affinity in a Group of 1-Aryl-5-(1-H-pyrrol-1-yl)-1-H-pyrazole-3-carbox¬amides. J Quan. Chem. 1, (2014).
  34. Fukui, K.Y., T. Shingu, H., Molecular Orbital Theory of Reactivity in Aromatic Hydrocarbons. J. Chem. Phys. 20, 722, (1952).
  35. Mulliken, R.S., Electronic Population Analysis on LCAO [Single Bond] MO Molecular Wave Functions. I. J. Chem. Phys, 23, 1833, (1955).
  36. Gómez Jeria, J., S, P. Castro-Latorre, and G. Kpotin, Quantum Chemi¬cal Study of the Relationships between Electronic Structure and Antiviral Activities against Influenza A H1N1, Enterovirus 71 and Coxsackie B3 viruses of some Pyrazine-1, 3-thiazine Hybrid Analogues. International J. R. App., N. and Soc. Sci.; 9, 49, (2017).
  37. Sebaugh, J., Guidelines for accurate EC50/IC50 estimation. Pharmaceuti¬cal statistics, Wiley Online Library.10, 128, (2011).
  38. Gómez-Jeria, J., D-Cent-QSAR: A program to generate Local Atomic Re¬activity Indices from Gaussian 03 log files. v. 1.0. Chile, 2014.
  39. Solís, R.G., J., A Density Functional Theory study of therelationships be¬tween electronic structure and metabotropic glutamate receptor subtype 5 affinity of 2-amino- and 2-halothiazole derivatives. Research J. Pharm, Bio. and Chem. Sci, 5, 1401, (2014).
  40. Gómez-Jeria, J.-S.S.L., M. & Robles N, A, A Density Functional Study of the Inhibition of Microsomal Prostaglandin E2 Synthase-1 by 2-aryl substituted quinazolin-4(3H)-one, pyrido[4,3-d]pyrimidin-4(3H)-one and pyrido[2,3-d]pyrimidin-4(3H)-one derivatives. Der Pharmacia Lettre. 7, 54, (2015).
  41. Gómez, J.A., J., A Theoretical Study of the Relationships between Elec¬tronic Structure and Receptor Affinity in a group 5-HT1A and 5-HT2A of ligands containing an isonicotinic nucleus. Chem R J. 2, 198, (2017).
  42. Gomez Jeria, J.S. and A. Robles Navarro, A theoretical study of the re¬lationships between electronic structure and inhibition of tumor necrosis factor by cyclopentenone oximes. Research j. phar. Bio. and chem. Sci., rjpbcs research j. pharm., bio. & chem. Sci. rjpbcs research j. pharm., bio. & chem. Sci., proddatur. 6, 1337, (2015).
  43. Gómez Jeria, J., S and G. Kpotin, Some remarks on the interpretation of the local atomic reactivity indices within the Klopman-Peradejordi-Gómez (KPG) method. Research J. Pharm, Bio. and Chem. Sci. 9, 550, (2018).
  44. K. Fukui, T.Y., C. Nagata y H. Shingu,, Molecular Orbital Theory of Ori¬entation in Aromatic, Heteroaromatic, and Other Conjugated Molecules. The J Chem Ph,. 22, 1433, (1954).
  45. Gomez Jeria, J., S, A Theoretical Study of the Relationships between Electronic Structure and Antifungal Activity against Botrytis cinerea and Colletotrichum lagenarium of a Group of Carabrone Hydrazone Derivatives. Research J. Pharm, Bio. and Chem Sci., 6, 688, (2015).
  46. Gómez-Jeria, J.-S.S.-G., R., A Density Functional Theory study of the relationships between electronic structure and metabotropic glutamate receptor subtype 5 affinity of 2-amino- and 2-halothiazole derivatives. J. Pharm, Bio. and Chem. Sci. 5, 1401, (2014).
  47. Geerlings, P.D.P., F. & Langenaeker, W., Conceptual density functional theory. Chemical reviews, ACS Publications. 103, 1793, (2003).
  48. Gatica Diaz, J. and J.S. Gómez Jeria, A Theoretical Study of the Rela¬tionships between Electronic Structure and Cytotoxicity of a group of N2-alkylated Quaternary β-Carbolines against nine Tumoral Cell Lines. Comput. Methods Drug Des. 4, 79, (2014).
  50. Gómez, J.M.G., Quantum-chemical study of the relationships between electronic structure and anti influenza activity. 1. The inhibition of cy¬tophatic effects produced by the influenza A/Guangdong Luohu/219/2006 (H1N1) strain in MDCK cells by substituted bisaryl amide compounds. j comput aid mol des. 4, 34, (2014).
  51. Gómez, J.K., G. K.; , H.-K.; , A. Mensah, J., A DFT study or the relation¬ship between the electronic structure and the antiplasmodial activity of a series of 4-anilino-2-trichloromethylquinazolines derivatives. World Sci¬entific News. 88, 138, (2017).
  52. Gómez, J.G., V., A quantum chemical analysis of the inhibition of α-glucosidase by a group of oxadiazole benzohydrazone derivatives. Der Pharma Chemic, 2016. 8: p. 2016.
  53. Gómez, J.L., M. Robles, N., A Density Functional Study of the Inhibition of Microsomal Prostaglandin E2 Synthase-1 by 2-aryl substituted quin¬azolin-4(3H)-one, pyrido[4,3-d]pyrimidin-4(3H)-one and pyrido[2,3-d] pyrimidin-4(3H)-one derivatives. Der Pharmacia Lettre. 7, 54, (2105).
  54. Gómez, J.R.N., A DFT study of the Inhibition of Carbonic Anhydrase Iso¬forms I, II, IX and XII by a Series of Benzenesulfonamides and Tetrafluo¬robenzenesulfonamides. AM J Chem and App. 2, 66, (2015).

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