In-Silico Anticancer activity of cow urine extract of Kappaphycus alvarezii
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1 Available online at ISSN: INTERNATIONAL JOURNAL OF NOVEL TRENDS IN PHARMACEUTICAL SCIENCES In-Silico Anticancer activity of cow urine extract of Kappaphycus alvarezii RESEARCH ARTICLE K. Gowri Shankar*, Albin T. Fleming, R.Vidhya, Sophy Nirmal Department of Advanced Zoology and Biotechnology, Loyola College, Chennai , India Article Info Article history Received 4 Dec 2013 Revised 10 Dec 2013 Accepted 18 Dec 2013 Available online 31Dec 2013 Keywords PDB-protein data bank, JNKc-Jun NH2-terminal kinases Abstract Cow urine therapy is an age old concept in Ayurveda that is concerned with using the components of cow urine for treating various body disorders. Phytochemical are the secondary metabolites of algae and medicinal plants and are considerably used in traditional cancer research. Homo sapiens c-jun NH2-terminal kinases (JNKs) are enzymes critical in chronic diseases. JNKs are proteins best known for its role in the activation of the c-jun/activator protein-1 (AP-1) transcription factor complex. Follistatin has several tumorigenesis functionality and most direct connections to cancer such as prostate, colon, and ovarian cancer. Targeting JNKs inhibition and Follistatin might initiate the clinical benefits in chronic disease like lung, skin and other cancers. In-Silico approach is an attempt at identifying the anticancer activity of cow urine extract of red algae Kappaphycus alvarezii Phytochemicals against the cancer target Homo sapiens JNKs and Follistatin. The dataset comprising of phytochemical compounds obtained from GCMS of algae for molecular docking in AutoDock 4.2. The ligands Cyclopentanepropanoic acid and Benzyl-malonic acid showed minimum binding energy 5.58 kcal/mol with c-jun NH2-terminal kinases (PDB ID-1JNK) and 5.01 kcal/mol with Follistatin (PDB ID-2BOU). The compound Cyclopentanepropanoic acid and Benzyl-malonic acid interacted with several amino acid residues, of which alanine-74 and serine-55 was found to be common among all the target enzymes for protein and hydrogen bond formation. Results of our study suggested that molecular docking approach could be a potential tool to identify the hydrogen bond interactions and the molecular mechanisms of diseases. It was concluded that Cyclopentanepropanoic acid and Benzyl-malonic acid ligands would be of potent drug targets to treat various cancers based on the docking approach. INTRODUCTION Cow urine therapy is an age old concept in Ayurveda that is concerned with using the components of cow urine for treating various body disorders. In context to urological disorders, cow urine is extremely beneficial because it provides some of the most basic vitamins and minerals into the body. While vitamin C is most prominent, cow urine also exhibits traces of gold and copper [1]. Kappaphycus alvarezii (syn. K. cottonii) is a species of red alga. It is one of the most important commercial sources of carrageenans, a family of gel-forming, viscosifying polysaccharides. Farming methods affect the character of the carrageenan that can be extracted from the seaweed. This algae grows to two meters long and is green or yellow in color. It is very fast-growing, known to double its biomass in 15 days [2]. The possible involvement of Follistatin in tumor angiogenesis supports the concept that this molecule may also facilitate the dissemination of tumor cells to distant organs via the angiogenic route. In line with this hypothesis, emerging evidence suggests that, at least in some tumors, FLS appears to facilitate the metastatic process [3-5]. Furthermore, van der Poel et al. [6] also show that rapamycin, a specific inhibitor of the mammalian To whom correspondence should be addressed: K. Gowri Shankar gowririshankar.88@gmail.com VOLUME 3 NUMBER 5 DEC
2 serine/threonine protein kinase mammalian target of rapamycin (mtor), inhibits PC3 prostate cancer cells proliferation by causing cell cycle arrest in G1 phase and that this phenomenon is associated with an increase in the expression levels of BMP-4 and a decrease in the levels of Follistatin. Mitogen activated protein kinase are the family of conserved signal proteins which regulate various cellular process [7]. One of the subfamily proteins, c-jun NH2-terminal kinases (JNKs) are a group of serine/threonine protein kinases [8]. JNK significant role is to regulate cellular processes like proliferation, differentiation and growth. The process of JNKs activation is mainly by inflammatory signals and stressors and is critical for expression levels in human tumors and cancer cells [9]. Up-regulation of JNKs level plays an important role in various cancers such as liver and prostate [10]. However there is no conclusive report as to whether the target enzymes for the cow urine algae extract ligands. In the present study, the structural models of the ligands in the JNKs inhibition and Follistatin binding sites has been carried out, which may facilitate further development. MATERIALS AND METHODS Cow urine extraction One and a half kg of fresh seaweed was surface sterilized with sterile distilled water and 0.1% mercuric chloride and placed in an earthen pot filled with 10 liters of fresh cow-urine collected from a single cow fed with the same type of feed throughout the study. The pot was incubated in a pit dug in the soil for 20 days. At every 24hrs interval, 500ml of crude extract was collected and condensed into a dry powder using water bath at 40 o C. Samples were collected continuously for 20 days [11]. Compound identification through GCMS of Kappaphycus alvarezii incubated cow urine [11] Table I. Selected compounds for Insilico approach No. RT Name of the compound Molecular Formula MW Peak Area % Cyclohexanecarboxaldehyde, 3,3-dimethyl-5-oxo- C 9 H 14 O ,3-Dihydro-7-methyl-1,4-benzoxazine-3-one C 9 H 9 NO Cyclopentanepropanoic acid C 8 H 14 O Benzylmalonic acid C 10 H 10 O Structure of secondary metabolites from chemspider server and chem3d pro 12.0 software. Fig 3. Cyclohexanecarboxaldehyde,3,3-dimethyl-5-oxo Fig 4. 2,3-Dihydro-7-methyl-1,4-benzoxazine-3-one VOLUME 3 NUMBER 5 DEC
3 Fig 5. Cyclopentanepropanoic acid Fig 6. Benzylmalonic acid Target protein from Protein Data Bank Fig 7. 1JNK Fig 8. 2BOU Docking through AutoDock 4.2 Fig 9. AutoDock tools VOLUME 3 NUMBER 5 DEC
4 Fig 10. Benzyl-malonic acid docked with 1JNK Fig 11. Cyclopentanepropanoic acid docked with 2BOU RESULTS AND DISCUSSION Table 2: 1JNK and 2BOU Docked with ligands using AutoDock 4.2 S.no COMPOUNDS PARAMETERS 1 3,3-Dimethyl-5- oxocyclohexanecarbaldehyde 2 7-Methyl-2H-1,4- benzoxazin-3(4h)-one 3 Cyclopentanepropanoic acid CANCER BIOMARKERS 1JNK Binding energy kcal/mol Number of conformations in Inhibition Constant, Ki um um (micromolar) Amino acid residues ALA 74 LYS191 SER55 No of atoms in hbonds 2 1 Binding energy kcal/mol B0U Number of conformations in Inhibition Constant, Ki mm 1.45mM uM Amino acid residues ALA74 LEU86 No of bonds 1 1 Binding energy kcal/mol Number of conformations in 3 10 Inhibition Constant, Ki mm 1.78mM uM Amino acid residues ALA74 SER55 LEU86 No of bonds Benzyl-malonic acid Binding energy kcal/mol Number of conformations in Inhibition Constant, Ki mm 81.14uM uM Amino acid residues ALA74 LYS191 SER55 ASN194 No of bonds 3 1 VOLUME 3 NUMBER 5 DEC
5 The ligands Cyclopentanepropanoic acid and Benzyl-malonic acid showed minimum binding energy 5.01 kcal/mol with Follistatin (PDB ID- 2BOU) and 5.58 kcal/mol with c-jun NH2-terminal kinases (PDB ID-1JNK). The compound Cyclopentanepropanoic acid and Benzyl-malonic acid interacted with several amino acid residues, of which alanine-749(1jnk) and serine-55(2bou) was found to be common among all the target enzymes for protein and hydrogen bond formation. The Inhibition Constant, Ki µm (micromolar) or mm for the ligands Cyclopentanepropanoic acid and Benzyl-malonic acid showed uM (2BOU) and 81.14uM (1JNK). Of all the ligands 3,3- Dimethyl-5-oxocyclohexanecarbaldehyde shows the highest inhibition constant of which um for 1JNK. The first low minimum binding energy Benzyl-malonic acid shows high number of three REFERENCE rezii 3. Gold E, Risbridger G. Activins and activin antagonists in the prostate and prostate cancer. Mol Cell Endocrinol, 2012, 359(1 2), Krneta J, Kroll J, Alves F, Prahst C, Sananbenesi F, Dullin C, Kimmina S, Phillips DJ, Augustin HG. Dissociation of angiogenesis and tumorigenesis in follistatin- and activin expressing tumors. Cancer Res, 2008, 66, Rossmanith W, Chabicovsky M, Grasl-Kraupp B, Peter B, Schausberger E, Schulte-Hermann R. Follistatin overexpression in rodent liver tumors: a possible mechanism to overcome activin growth control. Mol Carcinog, 35(1), 2002, Van der Poel HG, Hanrahan C, Zhong H, Simons JW. Rapamycin induces Smad activity in prostate cancer cell lines. Urol Res, 2003, 30(6), Johnson GL, Lapadat R. Mitogen-activated protein kinase pathways mediated by ERK, hydrogen atom bonds with three amino acid residues ALA74, LYS191, ASN194 for 1JNK. The second low minimum binding energy Cyclopentanepropanoic acid shows high number of two hydrogen atom bonds with two amino acid residues SER55, LEU86 for 2BOU. CONCLUSION Results of our study suggested that molecular docking approach could be a potential tool to identify the hydrogen bond interactions and the molecular mechanisms of diseases. It was concluded that Cyclopentanepropanoic acid and Benzyl-malonic acid ligands would be of potent drug targets to treat various cancers based on the docking approach. This work could be extended in future for identifying novel protein targets and de novo drugs. JNK and p38 protein kinases. Science, 2002, 298, Martin JH, Mohit AA, Miller CA. Developmental expression in the mouse nervous system of the p493f12 SAP kinase. Brain Res Mol Brain Res, 1996, 35, Wagner EF, Nebreda AR. Signal integration by JNK and p38 MAPK pathways in cancer development. Nat Rev Cancer, 2009, 9, Chang Q, Zhang Y, Beezhold K J, Bhatia D, Zhao H, Chen J et al., Sustained JNK1 activation is associated with altered histone H3 methylations in human liver cancer. J. Hepatol, 2009, 50, Venkatesh R, Shanthi S, Rajapandian K et al., Preliminary study on antixanthomonas activity, phytochemical analysis, and charecterization of antimicrobial compounds from kappaphycus alvarezii, Asian J Pharm Clin Res, 2011, 4, Arumugam M, Muthuswamy U, Kuppusamy A et al., Computational drug discovery of potential phosphodiesterase inhibitors using in silico studies. Asian Pacific Journal of Tropical Disease, 2012, S822-S826. VOLUME 3 NUMBER 5 DEC
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