Bioactive compounds as a potential inhibitor of colorectal cancer; an insilico study of Gallic acid and Pyrogallol

Document Type: Research/Original Article

Authors

Department of Microbiology, Raiganj University, Raiganj, WB, India

Abstract

Abstract
Introduction- Now a day’s colorectal cancer (CRC) is one of the most deadly cancers in the world. The objective of this investigation was to evaluate the protective effect of gallic acid and pyrogallol in colorectal cancer. Previous reports suggest that there is an association present between some tannase producing bacteria and colorectal cancer. Tannase hydrolyze tannic acid into gallic acid and pyrogallol. Are those compounds have any therapeutic effect on colorectal cancer? This study will help to find those quarries.
Methods-The remedial effect of gallic acid and pyrogallol was studied by descriptor properties and molecular docking methods. 100 CRC causing protein structures were docked in this investigation.
Results- Lipinski Rule of Five and other descriptor properties of those compounds have showed their nontoxic and therapeutic nature. Molecular docking studies have showed highest score -38.22 KJ/Mol with gallic acid and -33.6 KJ/Mol with pyrogallol.
Conclusion- This is the first report on docking investigation of these large numbers of protein. The findings of this research concluded that gallic acid and pyrogallol have a protective effect in colorectal cancer by stopping the effect of those CRC causing protein.

Keywords


  1. Testa U, Pelosi E, Castelli G. Colorectal cancer: genetic abnormalities, tumor progression, tumor heterogeneity, clonal evolution and tumor-initiating cells. Medical Sciences. 2018 Jun;6(2):31.
  2. Armaghany T, Wilson JD, Chu Q, Mills G. Genetic alterations in colorectal cancer. Gastrointestinal cancer research: GCR. 2012 Jan;5(1):19.
  3. Koveitypour Z, Panahi F, Vakilian M, Peymani M, Forootan FS, Esfahani MH, Ghaedi K. Signaling pathways involved in colorectal cancer progression. Cell & bioscience. 2019 Dec;9(1):1-4.
  4. Yuan S, Tao F, Zhang X, Zhang Y, Sun X, Wu D. Role of Wnt/β-catenin signaling in the chemoresistance modulation of colorectal cancer. BioMed research international. 2020 Mar 18;2020.
  5. Zhang L, Shay JW. Multiple roles of APC and its therapeutic implications in colorectal cancer. JNCI: Journal of the National Cancer Institute. 2017 Aug 1;109(8).
  6. Slaby O, Svoboda M, Michalek J, Vyzula R. MicroRNAs in colorectal cancer: translation of molecular biology into clinical application. Molecular cancer. 2009 Dec;8(1):1-3.
  7. Hoops TC, Traber PG. Molecular pathogenesis of colorectal cancer. Hematology/oncology clinics of North America. 1997 Aug 1;11(4):609-33.
  8. Awidi M, Ababneh N, Shomaf M, Al Fararjeh F, Owaidi L, AlKhatib M, Al Tarawneh B, Awidi A. KRAS and NRAS mutational gene profile of metastatic colorectal cancer patients in Jordan. Plos one. 2019 Dec 27;14(12):e0226473.
  9. Ligresti G, Militello L, Steelman LS, Cavallaro A, Basile F, Nicoletti F, Stivala F, McCubrey JA, Libra M. PIK3CA mutations in human solid tumors: role in sensitivity to various therapeutic approaches. Cell cycle. 2009 May 1;8(9):1352-8.
  10. Colussi D, Brandi G, Bazzoli F, Ricciardiello L. Molecular pathways involved in colorectal cancer: implications for disease behavior and prevention. International journal of molecular sciences. 2013 Aug;14(8):16365-85.
  11. Xu K, Wang L, Shu HK. COX-2 overexpression increases malignant potential of human glioma cells through Id1. Oncotarget. 2014 Mar;5(5):1241.
  12. Dixon DA, Blanco FF, Bruno A, Patrignani P. Mechanistic aspects of COX-2 expression in colorectal neoplasia. Prospects for Chemoprevention of Colorectal Neoplasia. 2013:7-37.
  13. Luu LJ, Price JT. BRAF mutation and its importance in colorectal cancer. Adv. Mol. Underst. Color. Cancer. 2019 Jan 17:1-8.
  14. Luu LJ, Price JT. BRAF mutation and its importance in colorectal cancer. Adv. Mol. Underst. Color. Cancer. 2019 Jan 17:1-8.
  15. De Almeida CV, de Camargo MR, Russo E, Amedei A. Role of diet and gut microbiota on colorectal cancer immunomodulation. World journal of gastroenterology. 2019 Jan 14;25(2):151.
  16. Huang P, Liu Y. A reasonable diet promotes balance of intestinal microbiota: prevention of precolorectal cancer. BioMed research international. 2019 Jul 25;2019.
  17. Jana A, Halder SK, Banerjee A, Paul T, Pati BR, Mondal KC, Mohapatra PK. Biosynthesis, structural architecture and biotechnological potential of bacterial tannase: a molecular advancement. Bioresource technology. 2014 Apr 1;157:327-40.
  18. Gavrilas LI, Ionescu C, Tudoran O, Lisencu C, Balacescu O, Miere D. The role of bioactive dietary components in modulating miRNA expression in colorectal cancer. Nutrients. 2016 Oct;8(10):590.
  19. Kang DY, Sp N, Jo ES, Rugamba A, Hong DY, Lee HG, Yoo JS, Liu Q, Jang KJ, Yang YM. The inhibitory mechanisms of tumor PD-L1 expression by natural bioactive gallic acid in non-small-cell lung cancer (NCLC) cells. Cancers. 2020 Mar;12(3):727.
  20. Biswas I, Mitra D, Bandyopadhyay AK, Mohapatra PK. Contributions of protein microenvironment in tannase industrial applicability: An in-silico comparative study of pathogenic and non-pathogenic bacterial tannase. Heliyon. 2020 Nov 1;6(11):e05359.
  21. Mohapatra PK, Biswas I, Mondal KC, Pati BR. Concomitant yield optimization of tannase and gallic acid by Bacillus licheniformis KBR6 through submerged fermentation: An industrial approach. Acta Biologica Szegediensis. 2020;64(2).
  22. López de Felipe F, de Las Rivas B, Muñoz R. Bioactive compounds produced by gut microbial tannase: implications for colorectal cancer development. Frontiers in microbiology. 2014 Dec 5;5:684.
  23. Noguchi N, Ohashi T, Shiratori T, Narui K, Hagiwara T, Ko M, Watanabe K, Miyahara T, Taira S, Moriyasu F, Sasatsu M. Association of tannase-producing Staphylococcus lugdunensis with colon cancer and characterization of a novel tannase gene. Journal of gastroenterology. 2007 May;42(5):346-51.
  24. Oehmcke-Hecht S, Mandl V, Naatz LT, Dühring L, Köhler J, Kreikemeyer B, Maletzki C. Streptococcus gallolyticus abrogates anti-carcinogenic properties of tannic acid on low-passage colorectal carcinomas. Scientific reports. 2020 Mar 13;10(1):1-0.
  25. Meng XY, Zhang HX, Mezei M, Cui M. Molecular docking: a powerful approach for structure-based drug discovery. Current computer-aided drug design. 2011 Jun 1;7(2):146-57.
  26. Bothara KG, Patil AU, Sexena A. Importance of docking studies in drug design. Indian journal of pharmaceutical sciences. 1998;60(6):333.
  27. Senger S, Verma T. Molecular Docking: A Powerful Approach for Structure based Drug Discovery. Research & Reviews: A Journal of Bioinformatics. 2016 Sep 18;3(2):15-9.
  28. Hubbard RE, Chen I, Davis B. Informatics and modeling challenges in fragment-based drug discovery. Current opinion in drug discovery & development. 2007 May 1;10(3):289-97.
  29. Hubbard RE, Chen I, Davis B. Informatics and modeling challenges in fragment-based drug discovery. Current opinion in drug discovery & development. 2007 May;10(3):289-97.
  30. Bergström CA, Norinder U, Luthman K, Artursson P. Molecular descriptors influencing melting point and their role in classification of solid drugs. Journal of chemical information and computer sciences. 2003 Jul 21;43(4):1177-85.
  31. Khan AU. Descriptors and their selection methods in QSAR analysis: paradigm for drug design. Drug discovery today. 2016 Aug 1;21(8):1291-302.
  32. Rezaei-Seresht H, Cheshomi H, Falanji F, Movahedi-Motlagh F, Hashemian M, Mireskandari E. Cytotoxic activity of caffeic acid and gallic acid against MCF-7 human breast cancer cells: An in silico and in vitro study. Avicenna journal of phytomedicine. 2019 Nov;9(6):574.
  33. Ulfa DM, Arsianti A, Radji MA. In silico docking studies of gallic acid structural analogs as BCL-XL inhibitor in cancer. Asian J Pharm Clin Res. 2017 Apr 1;4:119-22.
  34. Humaedi A, Arsiyanti A, Radji M. In Silico Molecular Docking Study of Gallic Acid and its Derivatives as Inhibitor BRAF Colon Cancer. International Journal of ChemTech Research. 2017;10(1):310-5.
  35. BIOVIA DS. Discovery Studio Modeling Environment, Release 2017, San Diego: DassaultSystèmes, 2016.
  36. Pedretti A, Mazzolari A, Vistoli G. VEGA ZZ: a versatile toolkit for drug design and protein modelling. InCongreso de Fisicoquímica Teórica y Computacional 2008 Dec 2.
  37. Kouranov A, Xie L, de la Cruz J, Chen L, Westbrook J, Bourne PE, Berman HM. The RCSB PDB information portal for structural genomics. Nucleic acids research. 2006 Jan 1;34(suppl_1):D302-5.
  38. Gasteiger E, Hoogland C, Gattiker A, Wilkins MR, Appel RD, Bairoch A. Protein identification and analysis tools on the ExPASy server. The proteomics protocols handbook. 2005:571-607.
  39. Lipinski CA. Lead-and drug-like compounds: the rule-of-five revolution. Drug Discovery Today: Technologies. 2004 Dec 1;1(4):337-41.
  40. Rösler A, Vandermeulen GW, Klok HA. Advanced drug delivery devices via self-assembly of amphiphilic block copolymers. Advanced drug delivery reviews. 2012 Dec 1;64:270-9.
  41. Lin LT, Hsu WC, Lin CC. Antiviral natural products and herbal medicines. Journal of traditional and complementary medicine. 2014 Jan 1;4(1):24-35.
  42. Zhang MQ, Wilkinson B. Drug discovery beyond the ‘rule-of-five’. Current opinion in biotechnology. 2007 Dec 1;18(6):478-88.
  43. Todeschini R, Consonni V. Molecular descriptors for chemoinformatics: volume I: alphabetical listing/volume II: appendices, references. John Wiley & Sons; 2009 Oct 30.
  44. Norgan AP, Coffman PK, Kocher JP, Katzmann DJ, Sosa CP. Multilevel parallelization of AutoDock 4.2. Journal of cheminformatics. 2011 Dec;3(1):1-9.
  45. Tian W, Chen C, Lei X, Zhao J, Liang J. CASTp 3.0: computed atlas of surface topography of proteins. Nucleic acids research. 2018 Jul 2;46(W1):W363-367.
  46. Ansary I, Roy H, Das A, Mitra D, Bandyopadhyay AK. Regioselective Synthesis, Molecular Descriptors of (1, 5‐Disubstituted 1, 2, 3‐Triazolyl) Coumarin/Quinolone Derivatives and Their Docking Studies against Cancer Targets. ChemistrySelect. 2019 Mar 29;4(12):3486-94.
  47. DeLano WL, Bromberg S. PyMOL user’s guide. DeLano Scientific LLC. 2004;629.
  48. Clark DE. What has polar surface area ever done for drug discovery?. Future medicinal chemistry. 2011 Mar;3(4):469-84.
  49. Palm K, Luthman K, Ungell AL, Strandlund G, Beigi F, Lundahl P, Artursson P. Evaluation of dynamic polar molecular surface area as predictor of drug absorption: comparison with other computational and experimental predictors. Journal of medicinal chemistry. 1998 Dec 31;41(27):5382-92.
  50. Hao MH. Theoretical calculation of hydrogen-bonding strength for drug molecules. Journal of chemical theory and computation. 2006 May 9;2(3):863-72.
  51. Wade RC, Goodford PJ. The role of hydrogen-bonds in drug binding. Progress in clinical and biological research. 1989 Jan 1;289:433-44.
  52. Viswanadhan VN, Ghose AK, Revankar GR, Robins RK. An estimation of the atomic contribution to octanol-water partition coefficient and molar refractivity from fundamental atomic and structural properties: Its uses in computer aided drug design. Mathematical and Computer Modelling. 1990 Jan 1;14:505-10.
  53. Iqbal MJ, Chaudhry MA. Thermodynamic study of three pharmacologically significant drugs: Density, viscosity, and refractive index measurements at different temperatures. The Journal of Chemical Thermodynamics. 2009 Feb 1;41(2):221-6.