Electrochemical Detection of Antioxidant Activities of 1,4-Dihydropyridine Derivatives

Abstract

Antioxidant is a molecule which retards the autooxidation of fats and oils. Antioxidants block the oxidation process which can cause damage to many cells in body helping to prevent diseases. Therefore, the importance of antioxidant is in increasing demand. So far many attempts have been carried out for developing to detect antioxidant activities. Among various analytical techniques, electrochemistry has been a more approp- riate way to determine antioxidant activity due to its ease of use and short-lasting application. In this study, it was aimed to determine antioxidant activities of recently synthesized condensed 1,4-dihydropyridine derivatives using disposable pencil graphite electrode. Cyclic voltammetry technique was used to determine oxidation potential value, and also differential pulse voltammetry technique was used to determine reduction potential values of the derivatives. To verify our results, nifedipine was used as a reference drug and conventional antioxidant activities were also used as a basis for comparison.

Keywords

• 1,4-Dihydropyridines,antioxidant activity,electrochemical methods,cyclic voltammetry,differential pulse voltammetry

1,4-Dihidropiridin Türevlerinin Antioksidan Aktivitelerinin Elektrokimyasal Tayini

Abstract

A ntioksidan katı ve sıvı yağların otoksidasyonunu geciktiren bir moleküldür. Antioksidanlar, hastalıkları engellemeye yardımcı olarak vücutta pekçok hücreye zarar verebilen oksidasyon sürecini bloke ederler. Bu yüzden, antioksidanın önemine olan talep giderek artmaktadır. Bugüne kadar, pek çok teşebbüs antioksidan aktivite tayininin geliştirilmesi için gerçekleştirilmiştir. Çok çeşitli analitik tekniklerin arasında, elektrokimya kullanım kolaylığına ve kısa sürede uygulanabilmesine bağlı olarak antioksidan aktivitesinin belirlenmesi için daha uygun bir yoldur. Bu çalışmada, yeni sentezlenen kondanse 1,4-dihidropiridin türevlerinin antioksidan aktivitelerinin atılabilir kalem grafit elektrot kullanılarak belirlenmesi amaçlanmıştır. Dönüşümlü voltametri tekniği türevlerin oksidasyon potansiyel değerinin ve aynı zamanda diferansiyel puls voltametri tekniği redüksiyon potansiyel değerinin belirlenmesi için kullanılmıştır. Sonuçlarımızın değerlendirilmesi için, nifedipin bir referans ilaç olarak ve konvensiyonel antioksidan aktiviteleri aynı zamanda karşılaştırma için bir temel olarak kullanılmıştır

Keywords

• 1,4-Dihidropiridinler,antioksidan aktivitesi,elektrokimyasal yöntemler,dönüşümlü voltametri,diferansiyel puls voltametrisi

References

1. Z. Ye, H. Song, Antioxidant vitamins intake and the risk of coronary heart disease: Meta-analysis of cohort studies, Eur. J. Cardiovas. Prev. Rehabil., 15 (2008) 26.
2. X. Wu, L. Gu, J. Holden, DB. Haytowitz, SE. Gebhardt, G. Beecher, RL. Prior, Development of a database for total antioxidant capacity in foods: a preliminary study, J. Food Compos. Anal., 17 (2004) 407.
3. AM. Pisoschi, MC. Cheregi, AF. Danet, Total antioxidant capacity of some commercial fruit juices: electrochemical and spectrophotometrical approaches, Molecules, 14 (2009) 480.
4. B. Halliwell, JMC. Gutteridge, Free Radicals in biology & medicine, Oxford University Press, Oxford, 1989.
5. T. Finkel, NJ. Holbrook, Oxidants, oxidative stress and the biology of ageing, Nature, 408 (2000) 239.
6. A. Kumar, G. Singh, BV. Sunil Kumar, SK. Meur, Modulation of antioxidant status and lipid peroxidation in erythrocyte by dietary supplementation during heat stress in buffaloes, Livest Sci., 138 (2011) 299.
7. K. Ezzedine, J. Latreille, E. Kesse-Guyot, P. Galan, S. Hercberg, C. Guinot, D. Malvy, Incidence of skin cancers during 5-year follow-up after stopping antioxidant vitamins and mineral supplementation, Eur. J. Cancer, 46 (2010) 3316.
8. R. Blomhoff, MH. Carlsen, LF. Andersen, DR. Jacobs Jr, Health benefits of nuts: potential role of antioxidants, Br. J. Nutr., 96 (2006) 52.

9. F. Bossert, H. Meyer, E. Wehinger, 4-Aryldihydropyridines, a New Class of Highly Active Calcium Antagonists, Angew. Chem. Int. Ed. Engl., 20 (1981) 762.
10. T. Sugihara, T. Kinoshita, S. Aoyagi, Y. Tsujino, T.
11. R. Mannhold, B. Jablonka, W. Voigt, K. Schönafinger, K. Schraven, Calcium- and calmodulin-antagonism of elnadipine derivatives: comparative SAR, Eur. J. Med. Chem., 27 (1992) 229.
12. JL. Reid, PA. Meredith, F. Pasanisi, Clinical pharmacological aspects of calcium antagonists and their therapeutic role in hypertension, J. Cardiovasc. Pharmacol., 7 (1985) 18.
13. R. Shan, C. Velazquez, EE. Knaus, Syntheses, calcium channel agonist-antagonist modulation activities, and nitric oxide release studies of nitrooxyalkyl 1,4-dihydro-2,6-dimethyl-3-nitro-4- (2,1,3-benzoxadiazol-4-yl) pyridine-5 carboxylate racemates, enantiomers, and diastereomers, J. Med. Chem., 47 (2004) 254.
14. EI. Ivanov, TV. Ponamareva, GN. Merkushev, GJ. Duburs, EA. Bisenieks, JR. Uldrikis, NV. Makarova, Abstract Book of the Ixth Soviet–Indian Symposium on the Chemistry of Natural Products, 1989, 87.
15. EA. Bisenieks, JR. Uldrikis, IE. Kirule, GD. Tirzitis, GJ. Duburs, Synthesis and antioxidant activities of 2-methyl-5-oxo-1,4-dihydroindeno[1,2-b]pyridines, Chem. Heterocycl. Compd., 18 (1982) 1187.
16. ZQ. Liu, Chemical methods to evaluate antioxidant ability, Chem. Rev., 110 (2010) 5675.
17. V. Goulas, AM. Gomez-Caravaca, V. Exarchou, IP. Gerothanassis, A. Segura-Carretero, AF. Gutierrez, Exploring the antioxidant potential of Teucrium polium extracts by HPLC-SPE-NMR and on-line radical-scavenging activity detection, Food Sci. Technol. Int., 46 (2012) 104.
18. M. Carini, G. Aldini, S. Furlanetto, R. Stefani, RM. Facino, LC coupled to ion-trap MS for the rapid screening and detection of polyphenol antioxidants from Helichrysum stoechas, J. Pharm. Biomed. Anal., 24 (2001) 517.
19. B. Bektaşoğlu, SE. Çelik, M. Özyürek, K. Güçlü, R. Apak, Novel hydroxyl radical scavenging antioxidant activity assay for water-soluble antioxidants using a modified CUPRAC method, Biochem. Biophys. Res. Commun., 345 (2006) 1194.
20. C. Lopez-Alarcon, A. Denicola, Evaluating the antioxidant capacity of natural product: A review on chemical and cellular-based assays, Anal. Chim. Acta, 763 (2013) 1.
21. C. Wei, AJ. Bard, MV. Mirkin, Scanning Electrochemical Microscopy 31. The Application of SECM to the Study of Charge Transfer Processes at the Liquid/Liquid Interface, J. Phys. Chem. B, 99 (1995) 16033.
22. M. Donten, Z. Stojek, F. Scholz, Electron transfer – ion insertion electrochemistry at an immobilised droplet: Probing the three-phase electrode-reaction zone with a Pt disk microelectrode, Electrochem. Commun., 4 (2002) 324.
23. F. Quentel, V. Mirceski, M. L’Her, M. Mladenov, F. Scholz, C. Elleouet, Comparative study of the thermodynamics and kinetics of the ion transfer across the liquid/liquid interface by means of three- phase electrodes, J. Phys. Chem. B, 109 (2005) 13228. Osakai, A mechanistic study of the oxidation of natural antioxidants at the oil/water interface using scanning electrochemical microscopy, J. Electroanal. Chem., 612 (2008) 241.
24. X. Lu, L. Hu, X. Wang, Thin-Layer Cyclic Voltammetric and Scanning Electrochemical Microscopic Study of Antioxidant Activity of Ascorbic Acid at Liquid/Liquid Interface, Electroanalysis, 17 (2005) 953.
25. T. Osakai, H. Jensen, H. Nagatani, DJ. Fermin, HH. Girault, Mechanistic Aspects Associated with the Oxidation of L-Ascorbic Acid at the 1,2-Dichloroethane Water Interface, J. Electroanal. Chem., 510 (2001) 43.
26. MS. Cosio, S. Buratti, S. Mannino, S. Benedetti, Use of an electrochemical method to evaluate the antioxidant activity of herb extracts from the Labiatae family, Food Chem., 97 (2006) 725.
27. T. Huang, P. Gao, MJ. Hageman, Rapid screening of antioxidants in pharmaceutical formulation development using cyclic voltammetry - potential and limitations, Curr. Drug Discov. Technol., 1 (2004) 173.
28. G. Tan, G. Bolat, MA. Onur, S. Abaci, Determination of lidocaine based on electrocatalysis of a chemically modified elecrode, Turk. J. Chem., 36 (2012) 593.
29. W. Gao, J. Song, N. Wu, Voltametric Behaviour and Square-Wave Voltametric Determination of Trepibutone at a Pencil Graphite Electrode, J. Electroanal. Chem., 576 (2005) 1.
30. D. Demetriades, A. Economou, A. Voulgaropoulos, A study of pencil-lead bismuth-film electrodes for the determination of trace metals by anodic stripping voltammetry, Anal. Chim. Acta, 519 (2004) 167.
31. H. Karadeniz, B. Gulmez, F. Sahinci, A. Erdem, GI. Kaya, N. Unver, B. Kivcak, M. Ozsoz, Disposable electrochemical biosensor for the detection of the interaction between DNA and lycorine based on guanine and adenine signals, J. Pharm. Biomed. Anal., 33 (2003) 295.
32. AM. Bond, PJ. Mahon, J. Schiewe, V. Vicente-Beckett, An Inexpensive and Renewable Pencil Electrode for use in Field-Based Stripping Voltammetry, Anal. Chim. Acta, 345 (1997) 67.
33. AA. Boldyrev, Paradoxes of cerebral oxidative metabolism, Biochemistry, 60 (1995) 1536.
34. SE. Forest, MJ. Stimson, JD. Simon, Mechanism for the photochemical production of superoxide by quinacrine, J. Phys. Chem. B, 103 (1999) 3963.
35. EI. Korotkova, YA. Karbainov, AV. Shevchuk, Study of antioxidant properties by voltammetry, J. Electroanal. Chem., 518 (2002) 56.
36. P. Arulpriya, P. Lalitha, S. Hemalatha, Cyclic voltammetric assessment of the antioxidant activity of petroleum ether extract of Samanea saman (Jacq.) Merr, Adv. Appl. Sci. Res., 1 (2010) 24.
37. MS. Akman, M. Girard, LF. O’Brien, AK. Ho, CL. Chik, Mechanisms of action of a second generation growth hormone-releasing peptide (Ala-His-D-Beta Nal-Ala- Trp-D-Phe-Lys-NH2) in rat anterior pituitary cells, Endocrinology, 132 (1993) 1286.
38. SL. Ali, Nifedipine, in: K. Florey (Eds.), Analytical Profiles of Drug Substances, Vol. 18, Academic Press, New York, 1989, 221.
39. KM. Kadish, JE. Anderson, Purification of solvents for electroanalysis: benzonitrile; dichloromethane; 1,1-dichloroethane and 1,2-dichloroethane, Pure Appl. Chem., 59 (1987) 703.
40. KM. Kadish, JQ. Ding, T. Malinski, Resistance of nonaqueous solvent systems containing tetraalkylammonium salts. Evaluation of heterogeneous electron transfer rate constants for the ferrocene/ferrocenium couple, Anal. Chem., 56 (1984) 1741.
41. DT. Sawyer, JL. Roberts Jr., Experimental Electrochemistry for Chemists, Chap. 5, Wiley, New York, 1995.
42. Y. Yan, EL. Zeitler, J. Gu, Y. Hu, AB. Bocarsly, Electrochemistry of Aqueous Pyridinium: Exploration of a Key Aspect of Electrocatalytic Reduction of CO2 to Methanol, J. Am. Chem. Soc., 135 (2013) 14020.
43. R. Salazar, PA. Navarrete-Encina, JA. Squella, C. Barrientos, V. Pardo-Jimenez, LJ. Nunez- Vergara, Study on the oxidation of C4-phenolic- 1,4-dihydropyridines and its reactivity towards superoxide radical anion in dimethyl sulfoxide, Electrochim. Acta, 56 (2010) 841.
44. D. Sun-Waterhouse, BG. Smith, CJ. O’Connor, LD. Melton, Effect of raw and cooked onion dietary fibre on the antioxidant activity of ascorbic acid and quercetin, Food Chem., 111 (2008) 580.
45. A. Eftekhari, Comments on “Li diffusion in LiNi0.5Mn0.5O2 thin film electrodes prepared by pulsed laser deposition” by Xia et al, Electrochim. Acta, 55 (2010) 3434.
46. R. Ramesham, MF. Rose, Kinetic studies of hydroquinone-quinone at the boron-doped diamond electrode by cyclic voltammetry, J. Mater. Sci. Lett., 16 (1997) 1693.
47. EI. Korotkova, EA. Mamaeva, NV. Bashkatova, AA. Bakibaev, Electrochemical determination of the antioxidant activity of 1,4-benzodiazepine, Pharm. Chem. J., 38 (2004) 170.
48. J. Pokorny, Are natural antioxidants better – and safer – than synthetic antioxidants, Eur. J. Lipid Sci. Technol., 109 (2007) 629.
49. A. Prakash, F. Rigelhof, E. Miller, In Medallion Laboratories; J. DeVries (Eds.), www.medallionlabs. com.