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Template Synthesis, Characterization, Antioxidant Effects, DNA Cleavage and Antimicrobial Studies of ZnII, NiII, MnII, CuII and CoII Complexes Containing Pyridazinone Moiety

Year 2020, Volume: 10 Issue: 1, 40 - 54, 25.06.2020
https://doi.org/10.37094/adyujsci.589071

Abstract

In this study, novel
five Schiff base metal complexes derived from Zn
II, NiII,
Mn
II, CuII and CoII metal salts and 5-benzoyl-4-hydroxy-2-methyl-6-phenyl-2H-pyridazine-3-one
with
o-aminophenol have been
synthesized using a template method. 
Metal complexes were characterized by elemental analysis, FT-IR, UV-Vis, Mass and magnetic susceptibility.  Antioxidant effects, DNA cleavage, and antimicrobial studies of synthesized compounds were performed. DPPH scavenging and metal chelating activity was found to increase with concentration. The highest DPPH activity and ferrous ion chelating activity were obtained from compound Zn. DNA cleavage studies indicated that all tested compounds were cleavage active at the concentration of 100 mg/L. While all the synthesized compounds displayed antibacterial activity against E. hirae in order of Mn>Zn=Ni=Co>Cu. The compound Ni only showed antimicrobial activity against all microorganisms tested, especially against L. pneumophila subsp. pneumophila with inhibition zone value equal to 13 mm.

Supporting Institution

Gaziantep University

Thanks

This study received no support from the fund.

References

  • [1] Bilgin, R., Yalcin, M.S., Yucebilgic, G., Koltas, I.S., Yazar, S., Oxidative stress in vivax malaria, The Korean Journal of Parasitology, 50, 375-377, 2012.
  • [2] Bajpai, V.K., Baek, K.H., Kang, S.C., Antioxidant and free radical scavenging activities of taxoquinone, a diterpenoid isolated from Metasequoia glyptostroboides, South African Journal of Botany, 111, 93–98, 2017.
  • [3] Gali, R., Banothu, J., Gondru, R., Bavantula, R., Velivela, Y., Crooks, P.A., One-pot multicomponent synthesis of indole incorporated thiazolylcoumarins and their antibacterial, anticancer and DNA cleavage studies, Bioorganic & Medicinal Chemistry Letters, 25, 106–112, 2015.
  • [4] Shebl, M., Adly, O.M.I., Abdelrhman, E.M., El-Shetary, B.A., Binary and ternary copper(II) complexes of a new Schiff base ligand derived from 4-acetyl-5,6-diphenyl-3(2H)-pyridazinone: Synthesis, spectral, thermal, antimicrobial and antitumor studies, Journal of Molecular Structure, 1145, 329-338, 2017.
  • [5] Lin, S., Liu, Z., Hu, Y., Microwave-enhanced efficient synthesis of diversified 3,6-disubstituted pyridazines, Journal of Combinatorial Chemistry,9, 742–744, 2007.
  • [6] Aleeva, G.N., Zhuravleva, M.V., Khafiz’yanova, R.K., The role of excipients in determining the pharmaceutical and therapeutic properties of medicinal agents, Pharmaceutical Chemistry Journal, 43, 230-234, 2009.
  • [7] Sönmez, M., Berber, I., Akbaş, E., Synthesis, antibacterial and antifungal activity of some new pyridazinone metal complexes, European Journal of Medicinal Chemistry, 41, 101–105, 2006.
  • [8] Akbas, E., Berber, I., Sener, A., Hasanov, B., Synthesis and antibacterial activity of 4-benzoyl-1-methyl-5-phenyl-1H-pyrazole-3-carboxylic acid and derivatives, Il Farmaco, 60, 23–26, 2005.
  • [9] Blois, M.S., Antioxidant determinations by the use of a stable free radical, Nature, 181, 1199, 1958.
  • [10] Hsu, C., Chen, W., Weng, Y., Tseng, C., Chemical composition, physical properties, and antioxidant activities of yam flours as affected by different drying methods, Food Chemistry, 83, 85–92, 2003.
  • [11] Kalemba, D., Kunicka, A., Antibacterial and antifungal properties of essential oils, Current Medicinal Chemistry, 10, 813–829, 2003.
  • [12] Roy, S., Mondal, T.K., Layek, A., Saha, R., Sinha, C., Structure, spectra and electrical conductivity of Copper(I) and Silver(I) phosphino bridging mixed ligand complexes with Coumarinyl Schiff base, Inorganica Chimica Acta, 469, 523-535, 2018.
  • [13] Hassan, N., El-Sonbati, A.Z., El-Desouky, M.G., Synthesis, characterization, molecular docking and DNA binding studies of Cu(II), Ni(II), Zn(II) and Mn(II) complexes, Journal of Molecular Liquids, 242, 293–307, 2017.
  • [14] Gao, X.S., Ni, C.C., Ren, X.M., Syntheses, crystal structures, photoluminescent and magnetic properties of complexes of zinc(II) and copper(II) with Schiff-base ligands derived from 2,6- diacetylpyridine, Polyhedron, 138, 225-231, 2017.
  • [15] Fernández-Souto, P., Romero, J., García-Vázquez, J.A., Sousa, A., Perez-Lourido, P., Electrochemical synthesis of a tetrahedral trinuclear nickel(II) complex with a tridentatedarene phosphinothiol ligand, Inorganic Chemistry Communications, 26, 28-30, 2012.
  • [16] Orojloo, M., Zolgharnein, P., Solimannejad, M., Amani, S., Synthesis and characterization of cobalt (II), nickel (II), copper (II) and zinc (II) complexes derived from two Schiff base ligands: Spectroscopic, thermal, magnetic moment, electrochemical and antimicrobial studies, Inorganica Chimica Acta, 467, 227-237, 2017.
  • [17] Khulbe, R.C., Singh, R.P., Bhoon, Y.K., Copper(II), nickel(II) and cobalt(II) complexes of pyridyl and quinolylhydrazones of isatin and methylisatin: Ligand dependent stereochemistry, Transition Metal Chemistry, 8, 59-61, 1983.
  • [18] Adly, O.M.I., Shebl, M., El-Shafiy, H.F., Khalil, S.M.E., Taha, A., Mahdi, M.A.N., Synthesis, spectroscopic characterization, antimicrobial and antitumor studies of mono-, bi- and tri-nuclear metal complexes of a new Schiff base ligand derived from o-acetoacetylphenol, Journal of Molecular Structure, 1150, 507-522, 2017.
  • [19] Kitzberger, C.S.G., Smania, J.A., Pedrosa, R.C., Ferreira, S.R.S., Antioxidant and antimicrobial activities of shiitake (Lentinula edodes) extracts obtained by organic solvents and supercritical fluids, Journal of Food Engineering, 80, 631-638, 2007.
  • [20] Ağırtas, M.S., Cabir, B., Özdemir, S., Novel metal (II) phthalocyanines with 3,4,5-trimethoxybenzyloxy-substituents: Synthesis, characterization, aggregation behaviour and antioxidant activity, Dyes and Pigments, 96, 152-157, 2013.

Piridazinon Yapısı İçeren ZnII, NiII, MnII, CuII ve CoII Komplekslerinin Şablon Sentezleri, Karakterizasyonları, Antioksidan Etkileri, DNA Klevajı ve Antimikrobiyal Etkilerinin Araştırılması

Year 2020, Volume: 10 Issue: 1, 40 - 54, 25.06.2020
https://doi.org/10.37094/adyujsci.589071

Abstract

Bu çalışmada template metodu ile o-aminofenol, 5-benzoil-4-hidroksi-2-metil-6-fenil-2Hpiridazin-3-on ve ZnII, NiII, MnII, CuII ve CoII metal tuzlarından türeyen beş yeni Schiff baz kompleksi sentezlenmiştir. Metal kompleksler elemental analiz, FT-IR, UV-Vis, kütle ve manyetik duyarlılık ile karakterize edilmiştir. Sentezlenen bileşiklerin antioksidan etkileri, DNA bölünmesi ve antimikrobiyal çalışmaları yapılmıştır. DPPH süpürme ve metal şelatlama aktivitesinin konsantrasyona bağlı olarak arttığı bulunmuştur. En yüksek DPPH aktivitesi ve demir iyon şelatlama aktivitesi Zn bileşiğinden elde edildi. Sentezlenen tüm bileşikler, Mn>Zn=Ni=Co>Cu sırasına gore E. hirae’ye karşı antibakteriyal aktivite sergilerken, sadece Ni bileşiği test edilen tüm organizmalara karşı, özellikle de L. pneumophila subsp. pneumophila’ya 13 mm’ye eşit inhibisyon zon değerinde antimikrobiyal aktivite göstermiştir.

References

  • [1] Bilgin, R., Yalcin, M.S., Yucebilgic, G., Koltas, I.S., Yazar, S., Oxidative stress in vivax malaria, The Korean Journal of Parasitology, 50, 375-377, 2012.
  • [2] Bajpai, V.K., Baek, K.H., Kang, S.C., Antioxidant and free radical scavenging activities of taxoquinone, a diterpenoid isolated from Metasequoia glyptostroboides, South African Journal of Botany, 111, 93–98, 2017.
  • [3] Gali, R., Banothu, J., Gondru, R., Bavantula, R., Velivela, Y., Crooks, P.A., One-pot multicomponent synthesis of indole incorporated thiazolylcoumarins and their antibacterial, anticancer and DNA cleavage studies, Bioorganic & Medicinal Chemistry Letters, 25, 106–112, 2015.
  • [4] Shebl, M., Adly, O.M.I., Abdelrhman, E.M., El-Shetary, B.A., Binary and ternary copper(II) complexes of a new Schiff base ligand derived from 4-acetyl-5,6-diphenyl-3(2H)-pyridazinone: Synthesis, spectral, thermal, antimicrobial and antitumor studies, Journal of Molecular Structure, 1145, 329-338, 2017.
  • [5] Lin, S., Liu, Z., Hu, Y., Microwave-enhanced efficient synthesis of diversified 3,6-disubstituted pyridazines, Journal of Combinatorial Chemistry,9, 742–744, 2007.
  • [6] Aleeva, G.N., Zhuravleva, M.V., Khafiz’yanova, R.K., The role of excipients in determining the pharmaceutical and therapeutic properties of medicinal agents, Pharmaceutical Chemistry Journal, 43, 230-234, 2009.
  • [7] Sönmez, M., Berber, I., Akbaş, E., Synthesis, antibacterial and antifungal activity of some new pyridazinone metal complexes, European Journal of Medicinal Chemistry, 41, 101–105, 2006.
  • [8] Akbas, E., Berber, I., Sener, A., Hasanov, B., Synthesis and antibacterial activity of 4-benzoyl-1-methyl-5-phenyl-1H-pyrazole-3-carboxylic acid and derivatives, Il Farmaco, 60, 23–26, 2005.
  • [9] Blois, M.S., Antioxidant determinations by the use of a stable free radical, Nature, 181, 1199, 1958.
  • [10] Hsu, C., Chen, W., Weng, Y., Tseng, C., Chemical composition, physical properties, and antioxidant activities of yam flours as affected by different drying methods, Food Chemistry, 83, 85–92, 2003.
  • [11] Kalemba, D., Kunicka, A., Antibacterial and antifungal properties of essential oils, Current Medicinal Chemistry, 10, 813–829, 2003.
  • [12] Roy, S., Mondal, T.K., Layek, A., Saha, R., Sinha, C., Structure, spectra and electrical conductivity of Copper(I) and Silver(I) phosphino bridging mixed ligand complexes with Coumarinyl Schiff base, Inorganica Chimica Acta, 469, 523-535, 2018.
  • [13] Hassan, N., El-Sonbati, A.Z., El-Desouky, M.G., Synthesis, characterization, molecular docking and DNA binding studies of Cu(II), Ni(II), Zn(II) and Mn(II) complexes, Journal of Molecular Liquids, 242, 293–307, 2017.
  • [14] Gao, X.S., Ni, C.C., Ren, X.M., Syntheses, crystal structures, photoluminescent and magnetic properties of complexes of zinc(II) and copper(II) with Schiff-base ligands derived from 2,6- diacetylpyridine, Polyhedron, 138, 225-231, 2017.
  • [15] Fernández-Souto, P., Romero, J., García-Vázquez, J.A., Sousa, A., Perez-Lourido, P., Electrochemical synthesis of a tetrahedral trinuclear nickel(II) complex with a tridentatedarene phosphinothiol ligand, Inorganic Chemistry Communications, 26, 28-30, 2012.
  • [16] Orojloo, M., Zolgharnein, P., Solimannejad, M., Amani, S., Synthesis and characterization of cobalt (II), nickel (II), copper (II) and zinc (II) complexes derived from two Schiff base ligands: Spectroscopic, thermal, magnetic moment, electrochemical and antimicrobial studies, Inorganica Chimica Acta, 467, 227-237, 2017.
  • [17] Khulbe, R.C., Singh, R.P., Bhoon, Y.K., Copper(II), nickel(II) and cobalt(II) complexes of pyridyl and quinolylhydrazones of isatin and methylisatin: Ligand dependent stereochemistry, Transition Metal Chemistry, 8, 59-61, 1983.
  • [18] Adly, O.M.I., Shebl, M., El-Shafiy, H.F., Khalil, S.M.E., Taha, A., Mahdi, M.A.N., Synthesis, spectroscopic characterization, antimicrobial and antitumor studies of mono-, bi- and tri-nuclear metal complexes of a new Schiff base ligand derived from o-acetoacetylphenol, Journal of Molecular Structure, 1150, 507-522, 2017.
  • [19] Kitzberger, C.S.G., Smania, J.A., Pedrosa, R.C., Ferreira, S.R.S., Antioxidant and antimicrobial activities of shiitake (Lentinula edodes) extracts obtained by organic solvents and supercritical fluids, Journal of Food Engineering, 80, 631-638, 2007.
  • [20] Ağırtas, M.S., Cabir, B., Özdemir, S., Novel metal (II) phthalocyanines with 3,4,5-trimethoxybenzyloxy-substituents: Synthesis, characterization, aggregation behaviour and antioxidant activity, Dyes and Pigments, 96, 152-157, 2013.
There are 20 citations in total.

Details

Primary Language English
Subjects Structural Biology
Journal Section Biology
Authors

Mehmet Sönmez 0000-0003-3127-666X

Özlem Bakırcı This is me 0000-0002-2263-8617

Hatice Gamze Soğukömeroğulları This is me 0000-0002-0575-8131

Sadin Özdemir 0000-0001-7384-7358

Mustafa Serkan Yalçın This is me 0000-0002-1134-5544

Publication Date June 25, 2020
Submission Date July 8, 2019
Acceptance Date March 26, 2020
Published in Issue Year 2020 Volume: 10 Issue: 1

Cite

APA Sönmez, M., Bakırcı, Ö., Soğukömeroğulları, H. G., Özdemir, S., et al. (2020). Template Synthesis, Characterization, Antioxidant Effects, DNA Cleavage and Antimicrobial Studies of ZnII, NiII, MnII, CuII and CoII Complexes Containing Pyridazinone Moiety. Adıyaman University Journal of Science, 10(1), 40-54. https://doi.org/10.37094/adyujsci.589071
AMA Sönmez M, Bakırcı Ö, Soğukömeroğulları HG, Özdemir S, Yalçın MS. Template Synthesis, Characterization, Antioxidant Effects, DNA Cleavage and Antimicrobial Studies of ZnII, NiII, MnII, CuII and CoII Complexes Containing Pyridazinone Moiety. ADYU J SCI. June 2020;10(1):40-54. doi:10.37094/adyujsci.589071
Chicago Sönmez, Mehmet, Özlem Bakırcı, Hatice Gamze Soğukömeroğulları, Sadin Özdemir, and Mustafa Serkan Yalçın. “Template Synthesis, Characterization, Antioxidant Effects, DNA Cleavage and Antimicrobial Studies of ZnII, NiII, MnII, CuII and CoII Complexes Containing Pyridazinone Moiety”. Adıyaman University Journal of Science 10, no. 1 (June 2020): 40-54. https://doi.org/10.37094/adyujsci.589071.
EndNote Sönmez M, Bakırcı Ö, Soğukömeroğulları HG, Özdemir S, Yalçın MS (June 1, 2020) Template Synthesis, Characterization, Antioxidant Effects, DNA Cleavage and Antimicrobial Studies of ZnII, NiII, MnII, CuII and CoII Complexes Containing Pyridazinone Moiety. Adıyaman University Journal of Science 10 1 40–54.
IEEE M. Sönmez, Ö. Bakırcı, H. G. Soğukömeroğulları, S. Özdemir, and M. S. Yalçın, “Template Synthesis, Characterization, Antioxidant Effects, DNA Cleavage and Antimicrobial Studies of ZnII, NiII, MnII, CuII and CoII Complexes Containing Pyridazinone Moiety”, ADYU J SCI, vol. 10, no. 1, pp. 40–54, 2020, doi: 10.37094/adyujsci.589071.
ISNAD Sönmez, Mehmet et al. “Template Synthesis, Characterization, Antioxidant Effects, DNA Cleavage and Antimicrobial Studies of ZnII, NiII, MnII, CuII and CoII Complexes Containing Pyridazinone Moiety”. Adıyaman University Journal of Science 10/1 (June 2020), 40-54. https://doi.org/10.37094/adyujsci.589071.
JAMA Sönmez M, Bakırcı Ö, Soğukömeroğulları HG, Özdemir S, Yalçın MS. Template Synthesis, Characterization, Antioxidant Effects, DNA Cleavage and Antimicrobial Studies of ZnII, NiII, MnII, CuII and CoII Complexes Containing Pyridazinone Moiety. ADYU J SCI. 2020;10:40–54.
MLA Sönmez, Mehmet et al. “Template Synthesis, Characterization, Antioxidant Effects, DNA Cleavage and Antimicrobial Studies of ZnII, NiII, MnII, CuII and CoII Complexes Containing Pyridazinone Moiety”. Adıyaman University Journal of Science, vol. 10, no. 1, 2020, pp. 40-54, doi:10.37094/adyujsci.589071.
Vancouver Sönmez M, Bakırcı Ö, Soğukömeroğulları HG, Özdemir S, Yalçın MS. Template Synthesis, Characterization, Antioxidant Effects, DNA Cleavage and Antimicrobial Studies of ZnII, NiII, MnII, CuII and CoII Complexes Containing Pyridazinone Moiety. ADYU J SCI. 2020;10(1):40-54.

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