ANTIRADICAL ACTIVITY OF L-GLUTAMINE, L-ASPARAGINE AND L-ASPARTIC ACID DERIVED REDUCED SCHIFF BASE COPPER(II) COMPLEXES

Authors

  • Lucia LINTNEROVÁ Department of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, Bratislava, Slovakia. Email: lintnerova@fpharm.uniba.sk. https://orcid.org/0000-0003-1442-9951
  • Jindra VALENTOVÁ Department of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, Bratislava, Slovakia. Corresponding author: lintnerova@fpharm.uniba.sk. https://orcid.org/0000-0003-2668-1767
  • Ferdinand DEVÍNSKY Department of Chemical Theory of Drugs, Faculty of Pharmacy, Comenius University, Bratislava, Slovakia. Email: devinsky@fpharm.uniba.sk. https://orcid.org/0000-0002-8059-9994

Keywords:

copper complexes, reduced Schiff bases, antiradical activity, SOD mimetics, INT method, amino acid derived ligands

Abstract

Superoxide dismutases (SOD) are a group of metallo-enzymes, containing one or two coordinated metals, and their main role in the organism is protection against superoxide radicals, one of the reactive oxygen species (ROS). Among these Cu(II)-Zn(II) SOD is present in cytoplasm and acts as a scavenger of superoxide radicals. Cu(II)-complexes may act as low-molecule analogue of Cu-Zn SOD and therefore are being studied as antiradical agents. In this study a series of Cu(II) complexes were synthesizes, containing ligands prepared from salicyl aldehyde and amino acids: L-asparagine, L-glutamine and L-aspartic acid. Complexes prepared from L-asparagine and L-glutamine are novel and were compared with the already reported complex Cu(HSal-L-Asp) hydrate (6e). An assay based on the ability to inhibit reduction of iodonitrotetrazolium dye (INT) by superoxide anion-radicals was used to determine antiradical activity of these complex. The prepared complexes - Cu(HSal-L-Asn) acetate (6a), Cu(HSal-L-Asn) hydrate (6b) and Cu(HSal-L-Gln) acetate (6c) proved to be good antiradical agents compared to complex 6e. The IC50 values of the radical transport were 19.2 ± 1.2 μM for 6a, 53.9 ± 9.4 μM for 6b and 4.11 ± 0.37 mM for 6c.

References

H. Sies, Experimental Physiology, 1997, 82, 291.

I. Ghoneim, A.B. Abdel-Naim, A.E. Khalifa, E.S. El-Denshary, Pharmacological Research, 2002, 46, 273.

S. Tozokumi, Free Radical Biology and Medicine, 1996, 34, 93.

S. Noguchi, Free Radical Biology and Medicine, 2002, 1588, 159.

B. Halliwell, Journal of Laboratory and Clinical Medicine, 1992, 119, 598.

D. Heimler, L. Isolani, P. Vignolini, A. Romani, Food Chemistry, 2009, 114, 765.

V. Mancebo-Campos, M. Desamparados Salvador, G. Fregapane, Food Chemistry, 2014, 150, 374.

D. Ravishankar, A.K. Rajora, F. Greco, H.M.I. Osborn, International Journal of Biochemistry & Cell Biology, 2013, 45, 2821.

C.-T. Yang, M. Vetrichelvan, X. Yang, B. Moubaraki, K.S. Murray, J.J. Vittal, Dalton Transactions, 2004, 1, 113.

L.A. Tavadyan, H.G. Tonikyan, S.H. Minasyan, L.A. Harutyunyan, F.T. Greenaway, S. Williams, R.A. Gray-Kaufman, J.R.J. Sorenson, Inorganica Chimica Acta, 2002, 328, 1.

M.S. Islas, T. Rojo, L. Lezama, M.G. Merino, M.A. Cortes, M.R. Puyol, E.G. Ferrer, P. A. M. Williams, Journal of Inorganic Biochemistry, 2013, 123, 23.

A. Klanicová, Z. Trávníček, J. Vančo, I. Popa, Z. Šindelář, Polyhedron, 2010, 29, 2582.

C.A. Kaştaş, G. Kaştaş, A. Güder, M. Gür, H. Muğlu, O. Büyükgüngör, Journal of Molecular Structure, 2016, in press.

N.S. Ilkevych, G. Schroeder, V.I. Rybachenko, K.Y. Chotiy, R.A. Makarova, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2012, 86, 821.

K. Wajda-Hermanowicz, D. Pieniążczak, R. Wróbel, A. Zatajska, Z. Ciunik, S. Berski, Journal of Molecular Structure, 2016, 1114, 108.

I.B. Afanas’ev, E.A. Ostrakhovitch, E.V. Mikhal’chik, G.A. Ibragimova, L.G. Korkina, Biochemical Pharmacology, 2001, 61, 677.

H.M. Ali, W. Almagribi, M.N. Al-Rashidi, Food Chemistry, 2016, 194, 1275.

K.M. Schaich, X. Tian, J. Xie, Journal of Functional Foods, 2015, 18, 782.

J. Vančo, J. Marek, Z. Trávníček, E. Račanská, J. Muselík, O. Švajlenová, Journal of Inorganic Biochemistry, 2008, 102, 595.

M.V. Nikolić, M.Ž. Mijajlović, V.V. Jevtić, Z.R. Ratković, S.B. Novaković, G.A. Bogdanović, J. Milovanović, A. Arsenijević, B. Stojanović, S.R. Trifunović, G.P. Radić, Journal of Molecular Structure, 2016, 1116, 264.

J. Vančo, O. Švajlenová, E. Račanská, J. Muselík, J. Valentová, Journal of Trace Elements in Medicine and Biology, 2004, 18, 155.

R.S. Hoonur, B.R. Patil, D.S. Badiger, R.S. Vadavi, K.B. Gudasi, P.R. Dandawate, M.M. Ghaisas, S.B. Padhye, M. Nethaji, European Journal of Medicinal Chemistry, 2010, 45, 2277.

P. Mishra, A. Dixit, M. Ray, S. C. Sabat, Biochimie, 2014, 97, 181.

F.O. Dimayuga, C. Wang, J.M. Clark, E.R. Dimayuga, V.M. Dimayuga, A.J. Bruce-Keller, Journal of Neuroimmunology, 2007, 182, 89.

V.A. Kostyuk, A.I. Potapovich, E.N. Strigunova, T.V. Kostyuk, I.B. Afanas'ev, Archives of Biochemistry and Biophysics, 2004, 428, 204.

Y. Ünver, K.K. Sancak, F. Çelik, E. Birinci, M. Küçük, S. Soylu, N.A. Burnaz, European Journal of Medicinal Chemistry, 2014, 84, 639.

M. Selvaganapathy, N. Pravin, K. Pothiraj, N. Raman, Journal of Photochemistry and Photobiology B: Biology, 2014, 138, 256.

S. Demir, A. Güder, T.K. Yazıcılar, S. Cağlar, O. Büyükgüngör, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015, 150, 821.

E. Pontiki, D. Hadjipavlou-Litina, A.T. Chaviara, C.A. Bolos, Bioorganic & Medicinal Chemistry Letters, 2006, 16, 2234.

L.H. Abdel-Rahman, A.M. Abu-Dief, M. Ismael, M.A.A. Mohamed, N.A. Hashem, Journal of Molecular Structure, 2016, 1103, 232.

J. Vančo, Z. Trávniček, J. Marek, R. Herchel, Inorganica Chimica Acta, 2010, 363, 3887.

A. García-Raso, J.J. Fiol, A. López-Zafra, J.A. Castro, A. Cabrero, I. Mata, E. Molins, Polyhedron, 2003, 22, 403.

L.H. Abdel-Rahman, R.M. El-Khatib, L.A.E. Nassr, A.M. Abu-Dief, M. Ismael, A.A. Seleem, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2014, 117, 366.

S. Mondal, B. Pakhira, A.J. Blake, M.G.B. Drew, S.K. Chattopadhyay, Polyhedron, 2016, 117, 327.

I. Yousuf, F. Arjmand, Journal of Photochemistry and Photobiology B: Biology, 2016, 164, 83.

B. Sreenivasulu, Australian Journal of Chemistry, 2009, 62, 968.

L. Jia, P. Jiang, J. Xu, Z. Hao, X. Xu, L. Chen, J. Wu, N. Tang, Q. Wang, J.J. Vittal, Inorganica Chimica Acta, 2010, 363, 855.

B. Sreenivasulu, J.J. Vittal, Inorganica Chimica Acta, 2009, 362, 2735.

F. Bao, X. Xu, W. Zhou, C. Pang, Z. Li, Z. Gu, Journal of Inorganic Biochemistry, 2014, 138, 73.

L. Jia, N. Tang, J. J. Vittal, Inorganica Chimica Acta, 2009, 362, 2525.

Downloads

Published

2016-12-30

How to Cite

LINTNEROVÁ, L. ., VALENTOVÁ, J. ., & DEVÍNSKY, F. . (2016). ANTIRADICAL ACTIVITY OF L-GLUTAMINE, L-ASPARAGINE AND L-ASPARTIC ACID DERIVED REDUCED SCHIFF BASE COPPER(II) COMPLEXES. Studia Universitatis Babeș-Bolyai Chemia, 61(4), 85–98. Retrieved from https://studia.reviste.ubbcluj.ro/index.php/chemia/article/view/8381

Issue

Section

Articles

Most read articles by the same author(s)

Similar Articles

<< < 13 14 15 16 17 18 19 20 21 22 > >> 

You may also start an advanced similarity search for this article.