2,038
Views
18
CrossRef citations to date
0
Altmetric
Research Article

Structure–activity relationships of fraxamoside as an unusual xanthine oxidase inhibitor

, , , & ORCID Icon
Pages 345-354 | Received 11 Aug 2016, Accepted 21 Oct 2016, Published online: 18 Jan 2017

References

  • Kelley EE, Khoo NKH, Hundley NJ, et al. Hydrogen peroxide is the major oxidant product of xanthine oxidase. Free Radic Biol Med 2010;48:493–8.
  • Rajendran P, Nandakumar N, Rengarajan T, et al. Antioxidants and human diseases. Clin Chim Acta 2014;436:332–47.
  • Becker MA, Jolly M. Hyperuricemia and associated diseases. Rheum Dis Clin North Am 2006;32:275–93.
  • Elion G. The purine path to chemotherapy. Science 1989;244:41–7.
  • Agarwal V, Hans N, Messerli FH. Effect of allopurinol on blood pressure: a systematic review and meta-analysis. J Clin Hypertens (Greenwich) 2013;15:435–42.
  • Garbe E. Exposure to allopurinol and the risk of cataract extraction in elderly patients. Arch Ophthalmol 1998;116:1652.
  • Thong BY-H. Stevens-Johnson syndrome/toxic epidermal necrolysis: an Asia-Pacific perspective. Asia Pac Allergy 2013;3:215–23.
  • Kumar R, Darpan Sharma S, Singh R. Xanthine oxidase inhibitors: a patent survey. Expert Opin Ther Pat 2011;21:1071–108.
  • Chauhan M, Kumar R. A comprehensive review on bioactive fused heterocycles as purine-utilizing enzymes inhibitors. Med Chem Res 2015;24:2259–82.
  • Chen C, Lü J-M, Yao Q. Hyperuricemia-related diseases and xanthine oxidoreductase (XOR) inhibitors: an overview. Med Sci Monit 2016;22:2501–12.
  • Takano Y, Hase-Aoki K, Horiuchi H, et al. Selectivity of febuxostat, a novel non-purine inhibitor of xanthine oxidase/xanthine dehydrogenase. Life Sci 2005;76:1835–47.
  • Ernst ME, Fravel MA. Febuxostat: a selective xanthine-oxidase/xanthine-dehydrogenase inhibitor for the management of hyperuricemia in adults with gout. Clin Ther 2009;31:2503–18.
  • Love BL, Barrons R, Veverka A, Snider KM. Urate-lowering therapy for gout: focus on febuxostat. Pharmacotherapy 2010;30:594–608.
  • Sahgal G, Ramanathan S, Sasidharan S, et al. In vitro antioxidant and xanthine oxidase inhibitory activities of methanolic Swietenia mahagoni seed extracts. Molecules 2009;14:4476–85.
  • Konno H, Kanai Y, Katagiri M, et al. Melinjo (Gnetum gnemon L.) seed extract decreases serum uric acid levels in nonobese Japanese males: a randomized controlled study. Evidence-Based Complement Altern Med 2013;2013:1–9.
  • Sweeney AP, Wyllie SG, Shalliker RA, Markham JL. Xanthine oxidase inhibitory activity of selected Australian native plants. J Ethnopharmacol 2001;75:273–7.
  • de Marino S, Festa C, Zollo F, et al. Antioxidant activity and chemical components as potential anticancer agents in the olive leaf (Olea europaea L. cv Leccino.) decoction. Anticancer Agents Med Chem 2014;14:1376–85.
  • Takenaka Y, Tanahashi T, Shintaku M, et al. Secoiridoid glucosides from Fraxinus americana. Phytochemistry 2000;55:275–84.
  • Panizzi L, Scarpati ML, Oriente G. The constitution of oleuropein, a bitter glucoside of the olive with hypotensive action. II. Gazz Chim Ital 1960;90:1449–85.
  • Inouye H, Yoshida T, Tobita S, et al. Absolute struktur des oleuropeins und einiger verwandter glucoside. Tetrahedron Lett 1970;11:2459–64.
  • Bergmeyer H, Gawehn K, Grassl M. Enzymes as biochemical reagents. In: Bergmeyer HU, ed. Methods of enzymatic analysis. 2nd ed. New York (NY): Academic Press Inc.; 1974:521–2.
  • de Marino S, Festa C, Zollo F, et al. Antioxidant activity of phenolic and phenylethanoid glycosides from Teucrium polium L. Food Chem 2012;133:21–8.
  • Hassinen T, Peräkylä M. New energy terms for reduced protein models implemented in an Off-Lattice force field. J Comput Chem 2001;22:1229–42.
  • Clark M, Cramer RD, Van Opdenbosch N. Validation of the general purpose tripos 5.2 force field. J Comput Chem 1989;10:982–1012.
  • Neese F. The ORCA program system. Wiley Interdiscip Rev Comput Mol Sci 2012;2:73–8.
  • Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 1993;98:5648.
  • Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ. Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J Phys Chem 1994;98:11623–7.
  • Schäfer A, Horn H, Ahlrichs R. Fully optimized contracted Gaussian basis sets for atoms Li to Kr. J Chem Phys 1992;97:2571.
  • Weigend F, Ahlrichs R. Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: design and assessment of accuracy. Phys Chem Chem Phys 2005;7:3297–305.
  • Grimme S. Density functional theory with London dispersion corrections. Wiley Interdiscip Rev Comput Mol Sci 2011;1:211–28.
  • Grimme S, Antony J, Ehrlich S, Krieg H. A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu. J Chem Phys 2010;132:154104
  • Sinnecker S, Rajendran A, Klamt A, et al. Calculation of solvent shifts on electronic g-tensors with the conductor-like screening model (COSMO) and its self-consistent generalization to real solvents (direct COSMO-RS). J Phys Chem A 2006;110:2235–45.
  • Neese F, Wennmohs F, Hansen A, Becker U. Efficient, approximate and parallel Hartree–Fock and hybrid DFT calculations. A “chain-of-spheres” algorithm for the Hartree–Fock exchange. Chem Phys 2009;356:98–109.
  • Schmidt MW, Baldridge KK, Boatz JA, et al. General atomic and molecular electronic structure system. J Comput Chem 1993;14:1347–63.
  • Fox T, Kollman PA. Application of the RESP methodology in the parametrization of organic solvents. J Phys Chem B 1998;102:8070–9.
  • Morris GM, Huey R, Lindstrom W, et al. AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comput Chem 2009;30:2785–91.
  • Götz AW, Williamson MJ, Xu D, et al. Routine microsecond molecular dynamics simulations with AMBER on GPUs. 1. Generalized born. J Chem Theory Comput 2012;8:1542–55.
  • Salomon-Ferrer R, Götz AW, Poole D, et al. Routine microsecond molecular dynamics simulations with AMBER on GPUs. 2. Explicit solvent particle mesh Ewald. J Chem Theory Comput 2013;9:3878–88.
  • Case DA, Darden TA, Cheatham III, TE, et al. AMBER 12, University of California, San Francisco [Internet] 2012. Available from: http://ambermd.org/doc12/Amber12.pdf.
  • Wang J, Wolf RM, Caldwell JW, et al. Development and testing of a general amber force field. J Comput Chem 2004;25:1157–74.
  • Kikuchi H, Fujisaki H, Furuta T, et al. Different inhibitory potency of febuxostat towards mammalian and bacterial xanthine oxidoreductases: insight from molecular dynamics. Sci Rep 2012;2:331.
  • Case DA, Darden TA, Cheatham III TE, et al. AMBER 13, University of California, San Francisco [Internet] 2012. Available from: http://ambermd.org/doc12/AmberTools13.pdf.
  • Ryckaert J-P, Ciccotti G, Berendsen HJ. Numerical integration of the Cartesian equations of motion of a system with constraints: molecular dynamics of n-alkanes. J Comput Phys 1977;23:327–41.
  • Naïm M, Bhat S, Rankin KN, et al. Solvated interaction energy (SIE) for scoring protein-ligand binding affinities. 1. Exploring the parameter space. J Chem Inf Model 2007;47:122–33.
  • Cui Q, Sulea T, Schrag JD, et al. Molecular dynamics-solvated interaction energy studies of protein-protein interactions: the MP1-p14 scaffolding complex. J Mol Biol 2008;379:787–802.
  • Coughlan MP, Rajagopalan KV, Handler P. The role of molybdenum in xanthine oxidase and related enzymes. Reactivity with cyanide, arsenite, and methanol. J Biol Chem 1969;244:2658–63.
  • Pick FM, McGartoll MA, Bray RC. Reaction of formaldehyde and of methanol with xanthine oxidase. Eur J Biochem 1971;18:65–72.
  • Bulotta S, Celano M, Lepore SM, et al. Beneficial effects of the olive oil phenolic components oleuropein and hydroxytyrosol: focus on protection against cardiovascular and metabolic diseases. J Transl Med 2014;12:219.
  • Nguyen MTT, Awale S, Tezuka Y, et al. Xanthine oxidase inhibitors from the flowers of Chrysanthemum sinense. Planta Med 2006;72:46–51.
  • Lin CM, Chen CS, Chen CT, et al. Molecular modeling of flavonoids that inhibits xanthine oxidase. Biochem Biophys Res Commun 2002;294:167–72.
  • Day AJ, Bao Y, Morgan MR, Williamson G. Conjugation position of quercetin glucuronides and effect on biological activity. Free Radic Biol Med 2000;29:1234–43.
  • Flemmig J, Kuchta K, Arnhold J, Rauwald HW. Olea europaea leaf (Ph.Eur.) extract as well as several of its isolated phenolics inhibit the gout-related enzyme xanthine oxidase. Phytomedicine 2011;18:561–6.