The Application of Novel Electrochemical Approach to Antioxidant Activity Assay of Metal Porphyrins with Bulky 3,5-Diisobornyl-4-hydroxyphenyl Moieties
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Author(s)
1Institute of Chemistry, Komi Scientific Center, Ural Branch, Russian Academy of Sciences, Syktyvkar, Russia.
2Department of Medicinal Chemistry and Fine Organic Synthesis, Lomonosov Moscow State University, Moscow, Russia.
3Institute of Physiologically Active Compounds of Russian Academy of Sciences, Chernogolovka, Moscow Region, Russia.
2Department of Medicinal Chemistry and Fine Organic Synthesis, Lomonosov Moscow State University, Moscow, Russia.
3Institute of Physiologically Active Compounds of Russian Academy of Sciences, Chernogolovka, Moscow Region, Russia.
The complexes of biogenic metals (Zn2+,Cu2+,Co2+,Mn3+,Fe3+) based on meso-tetra(3,5-diisobor-
nyl-4-hydroxyphenyl)porphyrin 1 were synthesized. The electrochemical
behavior of these com-pounds was studied using cyclic voltammetry (CV)
and rotating disk electrode (RDE) techniques. The antioxidant activity
of complexes was estimated by means of the electrochemical assay based
on the hydrogen atom transfer reaction to the stable radical
2,2’-diphenyl-1-picrylhydrazyl (DPPH). The RDE method was applied for
this process monitoring. It was shown that the efficiency of the metal
complexes (Cu2+,Co2+,Mn2+,Ni2+,Fe3+) is practically the same order as that of free base porphyrin 1. However the Zn2+
complex demonstrates significantly higher antioxidant activity, and the
stoichiometry of the reaction was determined as σ = 4. The results
demonstrate that porphyrin macrocycle can directly affect the
antioxidant properties of 2,6-diisobornylphenol.
KEYWORDS
Cite this paper
Rocheva, T. , Tyurin, V. , Belykh, D. , Moiseeva, А.
, Zhang, J. , Buravlev, Е. , Chukicheva, I. , Alexander Kutchin, A.
and Milaeva, E. (2014) The Application of Novel Electrochemical
Approach to Antioxidant Activity Assay of Metal Porphyrins with Bulky
3,5-Diisobornyl-4-hydroxyphenyl Moieties. American Journal of Analytical Chemistry, 5, 1028-1036. doi: 10.4236/ajac.2014.515109.
| [1] |
Migliore, L. and Coppedè, F.
(2009) Environmental-Induced Oxidative Stress in Neurodegenerative
Disorders and Aging. Mutation Research, 674, 73-84. http://dx.doi.org/10.1016/j.mrgentox.2008.09.013 |
| [2] |
Liu, Z.-Q. (2010) Chemical
Methods to Evaluate Antioxidant Ability. Chemical Reviews, 110,
5675-5691. http://dx.doi.org/10.1021/cr900302x |
| [3] |
Niki, E. (2010) Assessment of
Antioxidant Capacity in Vitro and in Vivo. Free Radical Biology and
Medicine, 49, 503-515. http://dx.doi.org/10.1016/j.freeradbiomed.2010.04.016 |
| [4] | Denisov, E.T. (1995) Handbook of Antioxidants: Bond Dissociation Energies, Rate Constants, Activation Energies, and Enthalpies of Reactions. CRC Press, Boca Raton, 174 p. |
| [5] |
Niki, E., Yoshida, Y., Saito, Y.
and Noguchi, N. (2005) Lipid Peroxidation: Mechanisms, Inhibition, and
Biological Effects. Biochemical and Biophysical Research Communications,
338, 668-676. http://dx.doi.org/10.1016/j.bbrc.2005.08.072 |
| [6] |
Buravlev, E.V., Chukicheva,
I.Yu., Belykh, D.V. and Kuchin, A.V (2007) Simple Synthesis of a
Terpenophenol-Chlorin Conjugate with an Amide Bond. Chemistry of Natural
Compounds, 43, 678-681. http://dx.doi.org/10.1007/s10600-007-0226-7 |
| [7] |
Milaeva, E.R. (2011) Metal-Based
Antioxidants-Potential Therapeutic Candidates for Prevention the
Oxidative Stress-Related Carcinogenesis: Mini-Review. Current Topics in
Medicinal Chemistry, 11, 2703-2713. http://dx.doi.org/10.2174/156802611798040741 |
| [8] | Plotnikov, M.B., Chernysheva, G.A., Smol’yakova, V.I., Ivanov, I.S., Kuchin, A.V., Chukicheva, I.Iu. and Krasnov, E.A. (2009) Neuroprotective Effects of Dibornol and Mechanism of Its Action in Rats with Cerebral Ischemia. Vestnik Rossiiskoi Akademii Meditsinskikh Nauk, 11, 12-17. (In Russian) |
| [9] |
Milaeva, E., Shpakovsky, D.,
Gracheva, Yu., Gerasimova, O., Tyurin, V. and Petrosyan, V. (2003) Oleic
Acid Peroxidation in the Presence of Metallo-Porphyrins. Journal of
Porphyrins and Phthalocyanines, 7, 719-724. http://dx.doi.org/10.1142/S1088424603000896 |
| [10] |
Milaeva, E.R., Gerasimova, O.A.,
Jingwei, Z., Shpakovsky, D.B., Syrbu, S.A., Semeykin, A.S., Koifman,
O.I., Kireeva, E.G., Shevtsova, E.F., Bachurin, S.O. and Zefirov, N.S.
(2008) Synthesis and Antioxidative Activity of Metalloporphyrins Bearing
2,6-Di-tert-butylphenol pendants. Journal of Inorganic Biochemistry,
102, 1348-1358. http://dx.doi.org/10.1016/j.jinorgbio.2008.01.022 |
| [11] |
Tyurin, V.Y., Zhang, J.,
Moiseeva, A.A., Milaeva, E.R., Belykh, D.V., Buravlev, E.V., Rocheva,
T.K., Chukicheva, I.Y. and Kuchin, A.V. (2013) Comparative Study of
Redox Characteristics and Antioxidant Activity of Porphyrins with
2,6-Dialkylphenol Groups. Doklady Chemistry, 450, 152-155. http://dx.doi.org/10.1134/S0012500813060025 |
| [12] | Rocheva, T.K., Belykh, D.V., Buravlev, E.V., Chukicheva, I.Y., Shevchenko, O.G. and Kutchin, A.V. (2013) Book of Abstracts of the 1st Conference on Medical Chemistry “MedChem Russia-2013”. Moscow, 252. (In Russian) |
| [13] | Tyurin, V.Y., Meleshonkova, N.N., Dolganov, A.V., Glukhova, A.P. and Milaeva, E.R. (2011) Electrochemical Method in Determination of Antioxidative Activity Using Ferrocene Derivatives as Examples. Russian Chemical Bulletin, 60, 647-655. |
| [14] |
Tyurin, V.Y., Wu, Y., Dolganov,
A.V. and Milaeva, E.R. (2011) Antioxidant Activity Assay of
2,6-Di-tert-butylphenols with Phosphonate Groups Using Cyclic
Voltammetry. Doklady Chemistry, 436, 31-33. http://dx.doi.org/10.1134/S0012500811020042 |
| [15] |
Tyurin, V.Y., Zhang, J.,
Glukhova, A. and Milaeva, E.R. (2011) Electrochemical Antioxidative
Activity Assay of Metalloporphyrins Bearing 2,6-Di-tert-butylphenol
Groups Based on Electrochemical DPPH-Test. Macroheterocycles, 4,
211-212. http://dx.doi.org/10.6060/mhc2011.3.10 |
| [16] |
Belykh, D.V., Rocheva, T.K.,
Buravlev, E.V., Chukicheva, I.Y. and Kutchin, A.V. (2012) The First
Tetra(meso-aryl)porphyrin with Isobornyl Substituents.
Macroheterocycles, 5, 121-124. http://dx.doi.org/10.6060/mhc2012.120572b |
| [17] | Gordon, A.J. and Ford, R.A. (1973) The Chemist’s Companion: A Handbook of Practical Data, Techniques and References. John Wiley and Sons, Inc., New York, 560 p. |
| [18] |
Solon, E. and Bard, A.J. (1964)
The Electrochemistry of Diphenylpicrylhydrazyl. Journal of the American
Chemical Society, 86, 1926-1928. http://dx.doi.org/10.1021/ja01064a005 |
| [19] |
Solon, E. and Bard, A.J. (1964)
Coulometric Study of the Reaction of Diphenylpicrylhydrazyl and Bromide
Ion. Journal of Physical Chemistry, 68, 1144-1147. http://dx.doi.org/10.1021/j100787a030 |
| [20] | Galus, Z. (1971) Teoretyczne podstawy elektroanalizy chemicznej: Polarografia, chronowoltamperometria, chronopotencjometria, metoda wirujacego dysku. Państwowe Wydawnictwo Naukowe, Warszawa, 390 p. |
| [21] | Brand-Williams, W., Cuvelier, M.E. and Berset, C. (1995) Use of a Free Radical Method to Evaluate Antioxidant Activity. LWT, Food Science and Technology, 28, 25-30. |
| [22] | Bondet, V., Brand-Williams, W. and Berset, C. (1997) Kinetics and Mechanisms of Antioxidant Activity Using the DPPH Free Radical Method. LWT, Food Science and Technology, 30, 609-615. |
| [23] |
Mishra, K., Ojha, H. and
Chaudhury, N.K. (2012) Estimation of Antiradical Properties of
Antioxidants Using DPPH Assay: A Critical Review and Results. Food
Chemistry, 130, 1036-1043. http://dx.doi.org/10.1016/j.foodchem.2011.07.127 |
| [24] |
Sharma, O.P. and Bhat, T.K.
(2009) DPPH Antioxidant Assay Revisited. Food Chemistry, 113, 1202-1205. http://dx.doi.org/10.1016/j.foodchem.2008.08.008 |
| [25] |
Meleshonkova, N.N., Shpakovsky,
D.B., Fionov, A.V., Dolganov, A.V., Magdesieva, T.V. and Milaeva, E.R.
(2007) Synthesis and Redox Properties of Novel Ferrocenes with Redox
Active 2,6-Di-tert-butylphenol Fragments: The First Example of
2,6-Di-tert-butylphenoxyl Radicals in Ferrocene System. Journal of
Organometallic Chemistry, 692, 5339-5344. http://dx.doi.org/10.1016/j.jorganchem.2007.08.013 eww141114lx |
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