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Electrochemical and spectroscopic study of l-dopa interaction with avarol

  • Đura Nakarada
  • Boris Pejin
  • Dušan Dimić
  • Ana Ivanović-Šašić
  • Zorica MojovićEmail author
  • Miloš Mojović
Article
  • 28 Downloads

Abstract

The electrochemistry of catecholamine neurotransmitters and their precursor l-dopa has been widely studied due to their relevance as biologically important compounds. The detection of these compounds from aqueous solution is hindered by the coexistence of quinone or hydroquinone. However, it was suggested that quinones adsorbed on the electrode surface can enhance catechol detection. In order to estimate the degree of interaction between quinones and l-dopa, cyclic voltammetry and UV–Vis spectroscopic study was performed. A sesquiterpenoid hydroquinone, isolated from the marine sponge Dysidea avara (avarol), has been used in this study. The change of apparent heterogeneous rate constant with different avarol/l-dopa ratio indicated that charge transfer could be enhanced at some extent. In addition to this, the obtained results for avarol and hydroquinone (its structural element) were compared. UV–Vis spectroscopic analysis confirmed interaction between l-dopa and avarol or hydroquinone. Taken all together, the interaction of l-dopa was stronger with hydroquinone than with avarol, presumably reflecting the conformational restrains of avarol caused by its terpenoid moiety.

Keywords

Avarol l-dopa Hydroquinone Cyclic voltammetry UV–Vis 

Notes

Acknowledgements

This work was supported by the Ministry of Education, Science and Technological Development of the Republic of Serbia, (Project Nos. III 45001, III 41005, OI 172053).

References

  1. 1.
    Misu Y, Ueda H, Goshima Y (1995) Neurotransmitter-like actions of L-DOPA. Adv Pharmacol 32:427–459CrossRefGoogle Scholar
  2. 2.
    Stansley B, Yamamoto B (2015) L-dopa and brain serotonin system dysfunction. Toxics 3:75–88CrossRefGoogle Scholar
  3. 3.
    Zorc B, Ljubić M, Antolić S, Filipović-Grčić J, Maysinger D, Alebić-Kolbah T, Jalšenjak I (1993) Macromolecular prodrugs. II. Esters of l-dopa and α-methyldopa. Int J Pharm 99:135–143CrossRefGoogle Scholar
  4. 4.
    Di Stefano A, Sozio P, Cerasa LS, Iannitelli A (2011) L-dopa prodrugs: an overview of trends for improving parkinsons disease treatment. Curr Pharm Des 17:3482–3493CrossRefGoogle Scholar
  5. 5.
    Sourkes TL (1971) Actions of levodopa and dopamine in the central nervous system. J Am Med Assoc 218:1909–1911CrossRefGoogle Scholar
  6. 6.
    Wang L, Bai J, Huang P, Wang H, Zhang L, Zhao Y (2006) Electrochemical behavior and determination of epinephrine at a penicillamine self-assembled gold electrode. Int J Electrochem Sci 1:238–249CrossRefGoogle Scholar
  7. 7.
    Guin PS, Das S, Mandal PC (2011) Electrochemical reduction of quinones in different media: a review. Int J Electrochem 2011:1–22CrossRefGoogle Scholar
  8. 8.
    Chen SM, Peng KT (2003) The electrochemical properties of dopamine, epinephrine, norepinephrine, and their electrocatalytic reactions on cobalt(II) hexacyanoferrate films. J Electroanal Chem 547:179–189CrossRefGoogle Scholar
  9. 9.
    Güell AG, Meadows KE, Unwin PR, MacPherson JV (2010) Trace voltammetric detection of serotonin at carbon electrodes: comparison of glassy carbon, boron doped diamond and carbon nanotube network electrodes. Phys Chem Chem Phys 12:10108–10114CrossRefGoogle Scholar
  10. 10.
    Zhang HM, Zhou XL, Hui RT, Li NQ, Liu DP (2002) Studies of the electrochemical behavior of epinephrine at a homocysteine self-assembled electrode. Talanta 56:1081–1088CrossRefGoogle Scholar
  11. 11.
    DuVall SH, McCreery RL (2000) Self-catalysis by catechols and quinones during heterogeneous electron transfer at carbon electrodes. J Am Chem Soc 122:6759–6764CrossRefGoogle Scholar
  12. 12.
    Zhang L, Teshima N, Hasebe T, Kurihara M, Kawashima T (1999) Flow-injection determination of trace amounts of dopamine by chemiluminescence detection. Talanta 50:677–683CrossRefGoogle Scholar
  13. 13.
    Garcia-Jimenez A, Teruel-Puche JA, Ortiz-Ruiz CV, Berna J, Tudela J, Garcia-Canovas F (2017) Study of the inhibition of 3-/4-aminoacetophenones on tyrosinase. Reac Kinet Mech Cat 120:1–13CrossRefGoogle Scholar
  14. 14.
    Minale L, Riccio R, Sodano G (1974) Avarol a novel sesquiterpenoid hydroquinone with a rearranged drimane skeleton from the sponge disidea avara. Tetrahedron Lett 15:3401–3404CrossRefGoogle Scholar
  15. 15.
    De Rosa S, Minale L, Riccio R, Sodano G (1976) The absolute configuration of avarol, a rearranged sesquiterpenoid hydroquinone from a marine sponge. J Chem Soc Perkin Trans 1(1):1408–1414CrossRefGoogle Scholar
  16. 16.
    De Rosa S, De Giulio A, Strazzullo G (1991) Biologically active metabolites from marine organisms and some semi-synthetic derivatives. Trends Org Chem 2:127–141Google Scholar
  17. 17.
    Pejin B, Iodice C, Tommonaro G, De Rosa S (2008) Synthesis and biological activities of thio-avarol derivatives. J Nat Prod 71:1850–1853CrossRefGoogle Scholar
  18. 18.
    Tommonaro G, García-Font N, Vitale RM, Pejin B, Iodice C, Cañadas S, Marco-Contelles J, Oset-Gasque MJ (2016) Avarol derivatives as competitive AChE inhibitors, non hepatotoxic and neuroprotective agents for Alzheimer’s disease. Eur J Med Chem 122:326–338CrossRefGoogle Scholar
  19. 19.
    Pejin B, Tommonaro G, Glumac M, Jakimov D, Kojic V (2017) The redox couple avarol/avarone in the fight with malignant gliomas: the case study of U-251 MG cells. Nat Prod Res 32(5):616–620CrossRefGoogle Scholar
  20. 20.
    Müller WEG, Böhm M, Batel R, De Rosa S, Tommonaro G, Müller IM, Schröder HC (2000) Application of cell culture for the production of bioactive compounds from sponges: synthesis of avarol by primmorphs from Dysidea avara. J Nat Prod 63:1077–1081CrossRefGoogle Scholar
  21. 21.
    Tabaković I, Davidović A, Müller WEG, Zahn RK, Sladić D, Dogović N, Gašić MJ (1987) Electrochemical reactivity of biologically active quinone/hydroquinone sesquiterpenoids on glassy carbon electrodes. Bioelectrochem Bioenerg 17:567–577CrossRefGoogle Scholar
  22. 22.
    Gašić MJ, Sladić D (1985) The avarol-avarone redox behaviour in acetonitrile. Croat Chem Acta 58:531–536Google Scholar
  23. 23.
    Eslami M, Namazian M, Zare HR (2013) Electrochemical behavior of 3,4-dihydroxyphenylalanine in aqueous solution. Electrochim Acta 88:543–551CrossRefGoogle Scholar
  24. 24.
    Liu X, Zhang Z, Cheng G, Dong S (2003) Spectroelectrochemical and voltammetric studies of L-DOPA. Electroanalysis 15:103–107CrossRefGoogle Scholar
  25. 25.
    Cervellati R, Greco E, Blagojević SM, Blagojević SN, Anić S, Čupić ŽD (2018) Experimental and mechanistic study of the inhibitory effects by phenolics on the oscillations of the Orbàn-Epstein reaction. React Kinet Mech Cat 123:125–139CrossRefGoogle Scholar
  26. 26.
    Gattrell M, Kirk DW (1993) A study of the oxidation of phenol at platinum and preoxidized platinum surfaces. J Electrochem Soc 140:1534–1540CrossRefGoogle Scholar
  27. 27.
    Kim M, Smith VP, Hong T (1993) First-and second-order derivative polarography/voltammetry for reversible, Quasi-reversible, and irreversible electrode processes. J Electrochem Soc 140:712–721CrossRefGoogle Scholar
  28. 28.
    Nicholson RS, Shain I (1964) Theory of stationary electrode polarography: single scan and cyclic methods applied to reversible, irreversible, and kinetic systems. Anal Chem 36:706–723CrossRefGoogle Scholar
  29. 29.
    Brown JH (2016) Analysis of two redox couples in a series: an expanded experiment to introduce undergraduate students to cyclic voltammetry and electrochemical simulations. J Chem Educ 93:1326–1329CrossRefGoogle Scholar
  30. 30.
    Lente G (2015) Deterministic kinetics in chemistry and systems biology. Springer, LondonCrossRefGoogle Scholar
  31. 31.
    Ortiz ME, Núñez-Vergara LJ, Squella JA (2003) Voltammetric determination of the heterogeneous charge transfer rate constant for superoxide formation at a glassy carbon electrode in aprotic medium. J Electroanal Chem 549:157–160CrossRefGoogle Scholar
  32. 32.
    Zhai C, Sun F, Zhang P, Ma H, Song A, Hao J (2016) Interactions of dopamine and dopamine hydrochloride with ethanol. J Mol Liq 223:420–426CrossRefGoogle Scholar
  33. 33.
    Barreto WJ, Ponzoni S, Sassi P (1999) A Raman and UV-Vis study of catecholamines oxidized with Mn(III). Spectrochim Acta Part A 55:65–72CrossRefGoogle Scholar
  34. 34.
    Ősz K (2008) A new, model-free calculation method to determine the coordination modes and distribution of copper(II) among the metal binding sites of multihistidine peptides using circular dichroism spectroscopy. J Inorg Biochem 102:2184–2195CrossRefGoogle Scholar
  35. 35.
    Wojdyr M (2010) Fityk: a general-purpose peak fitting program. J Appl Cryst 43:1126–1128CrossRefGoogle Scholar
  36. 36.
    Rowan T (1990) Functional stability analysis of numerical algorithms. Ph.D. thesis. Department of Computer Sciences, University of Texas at AustinGoogle Scholar

Copyright information

© Akadémiai Kiadó, Budapest, Hungary 2019

Authors and Affiliations

  1. 1.Faculty of Physical ChemistryUniversity of BelgradeBelgradeSerbia
  2. 2.Department of Life Sciences, Institute for Multidisciplinary Research – IMSIUniversity of BelgradeBelgradeSerbia
  3. 3.Department of Catalysis and Chemical Engineering, Institute of Chemistry, Technology and MetallurgyUniversity of BelgradeBelgradeSerbia

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