QUINIC ACID AS A POTENT DRUG CANDIDATE FOR PROSTATE CANCER – A COMPARATIVE PHARMACOKINETIC APPROACH
Abstract
Objective: Phytotherapy is growing importance with the emergence of deadly diseases. Prostate cancer is one such disease which is the most prevalent cancer afflicting men. Therapeutic application of plant is better understood with the pharmacological investigation of its phytoconstituents. Quinic acid is a prominent bioconstituent of flowers of Moringa oleifera Lam, a traditional plant of high nutritional and medicinal values. The present study analyzes the pharmacokinetic properties of this phytocomponent for its therapeutic application in prostate cancer.
Methods: In silico tools were used to screen the physicochemical, Lipinski-type and drug properties of Quinic acid from the other compounds used for comparison. The M. oleifera flower compound, Quinic acid and the standard therapeutic Curcumin were the ultimate compounds selected for further studies on their Adsorption-Distribution-Metabolism-Excretion (ADME) characteristics and toxicity parameters.
Results: The overall pharmacokinetics results indicated that Quinic acid had more number of advantages over Curcumin and the other compounds studied. Quinic acid possessed greater values of drug score and drug likeness with lesser brain penetration and lesser toxicity effects.
Conclusion: The study suggested that the pharmacokinetic properties of Quinic acid were more preferable to be used as a potent drug candidate to combat prostate cancer.
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Keywords: Prostate cancer, Quinic acid, Moringa oleifera, Pharmacokinetics, In silico tools, Drug candidate
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Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Delivery Rev 2001; 46(1-3): 3-26.
Lipinski CA. Lead- and drug-like compounds: the rule-of-five revolution. Drug Discov Today Technol 2004; 1(4): 337–341.
Ghose AK, Viswanadhan VN, Wendoloski JJ. A knowledge-based approach in designing combinatorial or medicinal chemistry libraries for drug discovery. 1. A qualitative and quantitative characterization of known drug databases. J Comb Chem 1999; 1(1): 55-68.
Ummanni R, Junker H, Zimmermann U, Venz S, Teller S, Giebel J, et al. Prohibitin identified by proteomic analysis of prostate biopsies distinguishes hyperplasia and cancer. Cancer Lett 2008; 266(2): 171-185.
Harwell JL. Plants used against cancer: a survey. Lloydia 1971; 34: 204-255.
Inbathamizh L, Padmini E. Effect of geographical properties on the phytochemical composition and antioxidant potential of Moringa oleifera flowers. BioMedRx 2013; 1(3): 239-247.
Inbathamizh L, Padmini E. Gas Chromatography-Mass Spectrometric analyses of methanol extract of Moringa oleifera flowers. International Journal of Chemical and Analytical Science 2012b; 3(5): 1394-1397.
Herrmann KM. The shikimate pathway: Early steps in the biosynthesis of aromatic compounds. The Plant Cell 1995; 7(7): 907-919.
Herrmann KM, Weaver LM. The shikimate pathway. Annu Rev Plant Physiol Plant Mol Biol 1999; 50: 473-503.
Pero RW, Lund H, Leanderson T. Antioxidant Metabolism Induced by Quinic Acid. Increased Urinary Excretion of Tryptophan and Nicotinamide. Phytotherapy Res 2009; 23(3): 335-346.
Soh Y, Kim JA, Sohn NW, Lee KR, Kim SY. Protective effects of quinic acid derivatives on tetrahydropapaveroline-induced cell death in C6 glioma cells. Biol Pharm Bull 2003; 26(6): 803-807.
Pero RW, Lund H. In Vivo Treatment of Humans with Quinic Acid Enhances DNA Repair and Reduces the Influence of lifestyle Factors on Risk to Disease. IJBB 2009; 5(3): 293-305.
Xiang T, Xiong QB, Ketut AI, Tezuka Y, Nagaoka T, Wu LJ and Kadota S. Studies on the hepatocyte protective activity and the structure-activity relationships of quinic acid and caffeic acid derivatives from the flower buds of Lonicera bournei. Planta Med 2001; 67(4): 322-325.
Inbathamizh L, Padmini E. In silico Studies On the Inhibitory Effects of Calcitriol and 5, 5’-Dithiobis-2-Nitrobenzoic Acid on Human Glucosaminyl N-Acetyl Transferase 1
Activity. Asian J Exp Biol Sci 2012a; 3(1): 14-21.
Inbathamizh L, Padmini E. In silico studies on the enhancing effect of anti-cancer phytochemicals of Moringa oleifera on cellular prostatic acid phosphatase activity. Drug Invention Today 2011; 3(8): 186-192.
Bolton E, Wang Y, Thiessen PA, Bryant SH. Pubchem: Integrated Platform of Small Molecules and Biological Activities. Annual Reports in Computational Chemistry. Washington DC: American Chemical Society; 2008. pp. 217-241. URL: pubchem.ncbi.nlm.nih.gov
Weininger D. SMILES, a Chemical Language and Information System. 1. Introduction to Methodology and Encoding Rules. J Chem Inf Comput Sci 1988; 28 (1): 31-36. URL: http://cactus.nci.nih.gov/translate
Li Z, Wan H, Shi Y, Ouyang P. Personal Experience with Four Kinds of Chemical Structure Drawing Software: Review on ChemDraw, ChemWindow, ISIS/Draw and ChemSketch. J Chem Inf Comput Sci 2004; 44(5): 1886-1890. URL: www.acdlabs.com
Thangaraj Sindhu, Sundaraj Rajamanikandan, Dhanapal Durgapriya, Jebamalai Raj Anitha, Selvaraj Akila, Velliyur Kanniyapan Gopalakrishnan. Molecular docking and QSAR studies on plant derived bioactive compounds as potent inhibitors of DEK oncoprotein. Asian J Pharm Clin Res 2011; 4(2): 67-71.
ACD/I-LAB 2.0. Advanced Chemistry Development, Inc. Toronto. On. Canada; 2012. URL: https://ilab.acdlabs.com/iLab2/
Thomas Sander. Actelion Pharmaceuticals Ltd. Allschwil. Switzerland; 2012. URL: http://www.organic-chemistry.org/prog/peo/
Leeson PD, Springthorpe B. The influence of drug-like concepts on decision-making in medicinal chemistry. Nat Rev Drug Discov 2007; 6(11): 881–890.
Veber DF, Johnson SR, Cheng HY, Smith BR, Ward KW, Kopple KD. Molecular properties that influence the oral bioavailability of drugs candidates. J Med Chem 2002; 45(12): 2615–2623.
Zakeri-Milani P, Tajerzadeh H, Islambolchilar Z, Barzegar S, Valizadeh H. The relation between molecular properties of drugs and their transport across the intestinal membrane. Daru 2006; 14(4): 164-171.
Pajouhesh H, Lenz GR. Medicinal chemical properties of successful central nervous system drugs. NeuroRx 2005; 2(4): 541–553.
Collandar R, Barlund H. Permeabilitatsstudien an Chara ceratophylla. Acta Bot Fenn 1932; 11: 1-14.
Waterbeemd H. Intestinal permeability prediction from theory. Oral drug absorption. Marcel Decker. New York; 2000. pp. 36-39.
Jay A, Walters WP, Murcko MA. Can we learn to distinguish between drug-like and nondrug-like molecules? J Med Chem 1998; 41: 3314-3324.
Leo A, Hansch C, Elkins D. Partition coefficients and their uses. Chem Rev 1971; 71(6): 525–616.
Vemula VR, Lagishetty V, Lingala S. Solubility enhancement techniques. Int J Pharm Sci Rev Res 2010; 5(1): 41–51.
Seydel JK, Schaper KJ. Quantitative structure-pharmacokinetic relationships and drug design. Pharmacol Ther 1981; 15(2): 131-182.
Toon S, Rowland M. Structure-pharmacokinetic relationships among the barbiturates in the rat. J Pharmacol Exp Ther 1983; 225(3): 752-763.
Lin JH. Bisphosphonates: a review of their pharmacokinetic properties. Bone 1996; 18(2): 75–85.
Watanabe J, Kozaki A. Relationship between partition coefficients and apparent volumes of distribution for basic drugs. II. Chem Pharm Bull 1978; 26(11): 3463-3470.
Shrikant M, Kalpana P. The effect of curcumin (turmeric) on Alzheimer's disease: An overview. Ann Indian Acad Neurol 2008; 11(1): 13–19.
Morita H, Wu J, Zipes DP. The QT syndromes: long and short. Lancet 2008; 372(9640): 750–763.
Hu CW, Sheng Y, Zhang Q, Liu HB, Xie X, Ma WC, et al. 2012. Curcumin inhibits hERG potassium channels in vitro. Toxicol Lett 2012; 208(2): 192-196.
Organization for Economic Cooperation and Development (OECD); 2013. URL: www.oecd.org/
Rong-Jen Shiau, Pie-Chun Shih, Yu-Der Wen. Effect of silymarin on curcumin-induced mortality in zebrafish (Danio rerio) embryos and larvae. Indian J Exp Biol 2011; 49: 491-497.
Walter P, Green S, Greene G, Krust A, Bornert JM, Jeltsch JM, et al. Cloning of the human estrogen receptor cDNA. Proc Natl Acad Sci USA 1985; 82(23): 7889–7893.
Greene GL, Gilna P, Waterfield M, Baker A, Hort Y, Shine J. Sequence and expression of human estrogen receptor complementary DNA. Science 1986; 231(4742): 1150–1154.
Harish K Handral, Shrishail Duggi, Ravichandra Handral, Tulsianand G, Shruthi SD. Turmeric: Nature’s precious medicine. Asian J Pharm Clin Res 2013; 6(3): 10-16.
Zhang L, Zhang J, Zhao B, Zhao-Wilson X. Quinic Acid Could Be a Potential Rejuvenating Natural Compound by Improving Survival of Caenorhabditis elegans under Deleterious Conditions. Rejuvenation Res 2012; 15(6): 573-583.
Aniza Pourtauborde. What Are the Most Common Curcumin Side Effects? WiseGeek; 2013. URL: http://www.wisegeek.org/
Jeffery Herman. The Adverse Properties of Curcumin. Livestrong; 2010. URL: http://www.livestrong.com/article/114509-adverse-properties-curcumin/
Marlene Alphonse. Side Effects of Turmeric Extract. Buzzle; 2011. URL: http://www.buzzle.com/articles/side-effects-of-turmeric-extract.html
Dellai A, Mansour HB, Limem I, Bouhlel I, Sghaier MB, Boubaker J, et al. Screening of antimutagenicity via antioxidant activity in different extracts from the flowers of Phlomis crinita Cav. ssp mauritanica munby from the center of Tunisia. Drug Chem Toxicol 2009; 32(3): 283-292.
Can OD, Ismail IB, Ozturk Y, Ozturk N, Potoglu-Erkara I, Sagratini G, et al. New antidepressant drug candidate: Hypericum montbretti extract. Nat Prod Res 2011; 25(15): 1469-1472.
Badreldin H Ali, Naser Al Wabel, Gerald Blunden. Phytochemical, pharmacological and toxicological aspects of Hibiscus sabdariffa L.: a review. Phytother Res 2005; 19(5): 369-375.
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