Research Article
Bakır(II) iyonunun 5,7-dihidroksiflavon ve sübstitue 2,2’-bipiridin ile yeni bir karışık ligand kompleksi
Abstract
Bu çalışmada 5,7-dihidroksiflavon (chrysin, chr) ve 4,4′-di-ter-bütil-2,2′-bipiridin (4,4’-dtbbpy) ligandları kullanılarak Cu(II) iyonunun yeni bir karışık ligand-bakır(II) koordinasyon bileşiği elde edildi. Sentezlenen bu koordinasyon bileşiğinin yapısı, elementel analiz, iletkenlik, manyetik süsseptibilite, kütle spektrometrisi ve Infrared (IR) spektroskopisi yöntemleriyle aydınlatıldı. Ayrıca TGA/DSC analizi ile yapısı desteklendi ve termal özellikleri araştırıldı. Elde edilen analiz verilerinden sentezlenen bileşikte, Cu(II) iyonu:chr-H:4,4’-dtbbpy oranının 1:1:1 olduğu ve koordinasyon küresi içerisinde ClO4- iyonunun bulunduğu nötral bir kompleks elde edildiği saptandı. Sonuç olarak sentezlenen koordinasyon bileşiği için [Cu(chr-H)(ClO4)(4,4’-dtbbpy)] formülü önerildi.
Supporting Institution
Bursa Uludağ Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon Birimi
Project Number
FHIZ-2021-440
Thanks
Bu çalışma Bursa Uludağ Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon Birimine bağlı yürütülen FHIZ-2021-440 Nolu proje ile desteklenmiştir. Desteklerinden dolayı Bursa Uludağ Üniversitesi Bilimsel Araştırma Projeleri Birimi’ne teşekkürlerimi sunarım.
References
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- Kopustinskiene, D.M., Jakstas, V., Savickas, A. ve Bernatoniene, J., Flavonoids as Anticancer Agents, Nutrients, 12, 2, 457, (2020).
- García-Lafuente, A., Guillamón, E., Villares, A., Rostagno, M.A. ve Martínez J.A., Flavonoids as antiinflammatory agents: implications in cancer and cardiovascular disease, Inflammation Research, 58, 537–552, (2009).
- Lalani, S. ve Poh, C.L., Flavonoids as Antiviral Agents for Enterovirus A71 (EV-A71), Viruses, 12, 2, 184, (2020).
- Cheong, H., Ryu, S.Y., Oak, M.H., Cheon, S.H., Yoo, G.S. ve Kim, K.M., Studies of structure activity relationship of flavonoids for the anti-allergic actions, Archives of Pharmacal Research, 21, 4, 478-480, (1998).
- Gryglewski, R.J., Korbut, R., Robak, J. ve Świȩs, J., On the mechanism of antithrombotic action of flavonoids, Biochemical Pharmacology, 36, 3, 317-322, (1987).
- Górniak, I., Bartoszewski, R. ve Króliczewski, J., Comprehensive review of antimicrobial activities of plant flavonoids, Phytochemistry Reviews, 18, 241–272, (2019).
- Islas, M.S., Naso L.G., Lezama, L., Valcarcel, M., Salado, C., Roura-Ferrer, M., Ferrer, E.G. ve Williams, P.A.M., Insights into the mechanisms underlying the antitumor activity of an oxidovanadium(IV) compound with the antioxidant naringenin. Albumin binding studies, Journal of Inorganic Biochemistry, 149, 12-24, (2015).
- Spoerlein, C., Mahal, K., Schmidt, H. ve Schobert, R., Effects of chrysin, apigenin, genistein and their homoleptic copper (II) complexes on the growth and metastatic potential of cancer cells, Journal of Inorganic Biochemistry, 127, 107-115, (2013).
- Tamayo, L.V., Gouvea, L.R., Sousa, A.C., Albuquerque, R.M., Teixeira S.F., de Azevedo R.A., Louro, S.R.W., Ferreira A.K. ve Beraldo, H., Copper(II) complexes with naringenin and hesperetin: cytotoxic activity against A 549 human lung adenocarcinoma cells and investigation on the mode of action, Biometals, 29, 39-52, (2016).
- Filho, J.C.C., Sarria, A.L.F., Becceneri, A.B., Fuzer, A.M., Batalhão, J.R., da Silva, C.M.P., Carlos, R.M., Vieira, P.C., Fernandes, J.B. ve Cominetti, M.R., Copper(II) and 2,2’-Bipyridine Complexation Improves Chemopreventive Effect of Naringenin against Breast Tumor Cells, PLOS ONE, 9, 9, e107058, (2014).
- Mutlu Gençkal, H., Erkisa, M., Alper, P., Sahin, S., Ulukaya, E. ve Ari, F., Mixed ligand complexes of Co(II), Ni(II) and Cu(II) with quercetin and diimine ligands: synthesis, characterization, anti cancer and anti oxidant activity. Journal of Biological Inorganic Chemistry, 25, 161–177, (2020).
- Mani, R., ve Natesan, V., Chrysin: Sources, beneficial pharmacological activities, and molecular mechanism of action. Phytochemistry, 145, 187-196, (2018).
- Shoosshtari, M.K., Sarkaki, A., Mansouri, S.M.T., Badavi, M., Khorsandi, L., Dehcheshmeh, M.G. ve Farbood , Y., Protective effects of Chrysin against memory impairment, cerebral hyperemia and oxidative stress after cerebral hypoperfusion and reperfusion in rats, Metabolic Brain Disease, 35, 401–412, (2020).
- Hea, X.-L., Wang, Y.-H., Bi, M.-G. ve Du, G.-H., Chrysin improves cognitive deficits and brain damage induced by chronic cerebral hypoperfusion in rats, European Journal of Pharmacology, 680, 1-3, 41–48, (2012).
- Shoieb, S.M., Esmat, A., Khalifa, A.E. ve Abdel-Naim, A.B., Chrysin attenuates testosterone-induced benign prostate hyperplasia in rats, Food and Chemical Toxicology, 111, 650-659, (2018).
- Mutlu Gençkal, H., New heteroleptic Cu(II) complexes of chrysin with 2,2ꞌ–bipyridine and substituted 1,10–phenanthrolines: Synthesis, characterization, thermal stability and antioxidant activity, Journal of Molecular Structure, 1209, 127917, (2020).
- Geary, W.J., The use of conductivity measurements in organic solvents for the characterisation of coordination compounds, Coordination Chemistry Reviews, 7, 1, 81-122, (1971).
- Vishwakarma, P.K., Mir J.M. ve Maurya, R.C., Pyrone-based Cu(II) complexes, their characterization, DFT based conformational drift from square planar to square pyramidal geometry and biological activities, Journal of Chemical Sciences, 128, 4, 511–522, (2016).
- Amani, V., Safari, N. ve Khavasi, H.R., Synthesis, characterization and crystal structure determination of iron(III) hetero-ligand complexes containing 2,2’-bipyridine, 5,5’-dimethyl-2,2’-bipyridine and chloride, [Fe(bipy)Cl4][bipyH] and [Fe(dmbipy)2Cl2][FeCl4], Polyhedron, 26, 15, 4257–4262, (2007).
- Kaushal, R., Kumar, N., Awasthi, P. ve Nehra K., Syntheses, characterization, and antibacterial study of titanium complexes, Turkish Journal of Chemistry, 37, 6, 936-945, (2013).
- Yilmaz, İ., Synthesis, structural characterization, and thermal properties of octahedral diperchlorato complexes of copper(II) with the chelating 2-aminomethylpiperidine and 2-aminomethylpyridine ligands, Inorganic and Nano-Metal Chemistry, 53, 4, 333-339, (2023).
- Pusz, J. ve Nitka, B., Synthesis and physicochemical properties of the complexes of Co (II), Ni (II), and Cu (II) with chrysin, Microchemical Journal, 56, 3, 373-381, (1997).
- Halevas, E., Mitrakas, A., Mavroidi, B., Athanasiou, D., Gkika, P., Antoniou, K., Samaras, G., Lialiaris, E., Hatzidimitriou, A., Pantazaki, A., Koukourakis, M., Sagnou, M., Pelecanou, M. ve Lialiaris, T., Structurally characterized copper-chrysin complexes display genotoxic and cytotoxic activity in human cells, Inorganica Chimica Acta, 515, 120062, (2021).
- Roy, S., Sil, A. ve Chakraborty, T., Potentiating apoptosis and modulation of p53, Bcl2, and Bax by a novel chrysin ruthenium complex for effective chemotherapeutic efficacy against breast cancer, Journal of Cellular Physiology, 234, 4, 4888–4909, (2019).
- Dalal, A., Nehra, K., Hooda, A., Singh, D., Kumar, S. ve Malik, R.S., Synthesis, photophysical characteristics and geometry optimization of Tris(2-benzoylacetophenonate)europium complexes with 2,2′-Bipyridine derivatives, Journal of Luminescence, 247, 118873, (2022).
A new mixed ligand complex of copper(II) Ion with 5,7-dihydroxyflavone and substituted 2,2'-bipyridine
Abstract
In this study, a new mixed ligand-copper(II) coordination compound of Cu(II) ion was obtained by using 5,7-dihydroxyflavone (chrysin, chr) and 4,4′-di-tert-butyl-2,2′-bipyridine (4,4’-dtbbpy) ligands. The structure of this synthesized coordination compound was elucidated by elemental analysis, conductivity, magnetic susceptibility, mass spectrometry and Infrared (IR) spectroscopy methods. In addition, its structure was supported by TGA/DSC analysis and its thermal properties were investigated. From the analysis data obtained, in the synthesized compound it was determined that the ratio of Cu(II) ion:chr-H: 4,4’-dtbbpy was 1:1:1 and a neutral complex was obtained with ClO4- ion in the coordination sphere. As a result, the formula [Cu(chr-H)(ClO4)(4,4'-dtbbpy)] was proposed for the synthesized coordination compound.
Project Number
FHIZ-2021-440
References
- Coşkun, P. ve İnci, H., Propolisin kimyasal içeriği ile antibakteriyel, antiviral ve antioksidan aktivitesi, ISPEC Journal of Agricultural Sciences, 4, 4, 1053-1070, (2020).
- Pietta, P.G., Flavonoids as Antioxidants, Journal of Natural Products, 63, 7, 1035–1042, (2000).
- Wang, L., Tu, Y.C., Lian, T.W., Hung, J.T., Yen, J.H. ve Wu, M.J., Distinctive antioxidant and anti-inflammatory effects of flavonols, Journal of Agricultural and Food Chemistry, 54, 26, 9798–9804, (2006).
- Kopustinskiene, D.M., Jakstas, V., Savickas, A. ve Bernatoniene, J., Flavonoids as Anticancer Agents, Nutrients, 12, 2, 457, (2020).
- García-Lafuente, A., Guillamón, E., Villares, A., Rostagno, M.A. ve Martínez J.A., Flavonoids as antiinflammatory agents: implications in cancer and cardiovascular disease, Inflammation Research, 58, 537–552, (2009).
- Lalani, S. ve Poh, C.L., Flavonoids as Antiviral Agents for Enterovirus A71 (EV-A71), Viruses, 12, 2, 184, (2020).
- Cheong, H., Ryu, S.Y., Oak, M.H., Cheon, S.H., Yoo, G.S. ve Kim, K.M., Studies of structure activity relationship of flavonoids for the anti-allergic actions, Archives of Pharmacal Research, 21, 4, 478-480, (1998).
- Gryglewski, R.J., Korbut, R., Robak, J. ve Świȩs, J., On the mechanism of antithrombotic action of flavonoids, Biochemical Pharmacology, 36, 3, 317-322, (1987).
- Górniak, I., Bartoszewski, R. ve Króliczewski, J., Comprehensive review of antimicrobial activities of plant flavonoids, Phytochemistry Reviews, 18, 241–272, (2019).
- Islas, M.S., Naso L.G., Lezama, L., Valcarcel, M., Salado, C., Roura-Ferrer, M., Ferrer, E.G. ve Williams, P.A.M., Insights into the mechanisms underlying the antitumor activity of an oxidovanadium(IV) compound with the antioxidant naringenin. Albumin binding studies, Journal of Inorganic Biochemistry, 149, 12-24, (2015).
- Spoerlein, C., Mahal, K., Schmidt, H. ve Schobert, R., Effects of chrysin, apigenin, genistein and their homoleptic copper (II) complexes on the growth and metastatic potential of cancer cells, Journal of Inorganic Biochemistry, 127, 107-115, (2013).
- Tamayo, L.V., Gouvea, L.R., Sousa, A.C., Albuquerque, R.M., Teixeira S.F., de Azevedo R.A., Louro, S.R.W., Ferreira A.K. ve Beraldo, H., Copper(II) complexes with naringenin and hesperetin: cytotoxic activity against A 549 human lung adenocarcinoma cells and investigation on the mode of action, Biometals, 29, 39-52, (2016).
- Filho, J.C.C., Sarria, A.L.F., Becceneri, A.B., Fuzer, A.M., Batalhão, J.R., da Silva, C.M.P., Carlos, R.M., Vieira, P.C., Fernandes, J.B. ve Cominetti, M.R., Copper(II) and 2,2’-Bipyridine Complexation Improves Chemopreventive Effect of Naringenin against Breast Tumor Cells, PLOS ONE, 9, 9, e107058, (2014).
- Mutlu Gençkal, H., Erkisa, M., Alper, P., Sahin, S., Ulukaya, E. ve Ari, F., Mixed ligand complexes of Co(II), Ni(II) and Cu(II) with quercetin and diimine ligands: synthesis, characterization, anti cancer and anti oxidant activity. Journal of Biological Inorganic Chemistry, 25, 161–177, (2020).
- Mani, R., ve Natesan, V., Chrysin: Sources, beneficial pharmacological activities, and molecular mechanism of action. Phytochemistry, 145, 187-196, (2018).
- Shoosshtari, M.K., Sarkaki, A., Mansouri, S.M.T., Badavi, M., Khorsandi, L., Dehcheshmeh, M.G. ve Farbood , Y., Protective effects of Chrysin against memory impairment, cerebral hyperemia and oxidative stress after cerebral hypoperfusion and reperfusion in rats, Metabolic Brain Disease, 35, 401–412, (2020).
- Hea, X.-L., Wang, Y.-H., Bi, M.-G. ve Du, G.-H., Chrysin improves cognitive deficits and brain damage induced by chronic cerebral hypoperfusion in rats, European Journal of Pharmacology, 680, 1-3, 41–48, (2012).
- Shoieb, S.M., Esmat, A., Khalifa, A.E. ve Abdel-Naim, A.B., Chrysin attenuates testosterone-induced benign prostate hyperplasia in rats, Food and Chemical Toxicology, 111, 650-659, (2018).
- Mutlu Gençkal, H., New heteroleptic Cu(II) complexes of chrysin with 2,2ꞌ–bipyridine and substituted 1,10–phenanthrolines: Synthesis, characterization, thermal stability and antioxidant activity, Journal of Molecular Structure, 1209, 127917, (2020).
- Geary, W.J., The use of conductivity measurements in organic solvents for the characterisation of coordination compounds, Coordination Chemistry Reviews, 7, 1, 81-122, (1971).
- Vishwakarma, P.K., Mir J.M. ve Maurya, R.C., Pyrone-based Cu(II) complexes, their characterization, DFT based conformational drift from square planar to square pyramidal geometry and biological activities, Journal of Chemical Sciences, 128, 4, 511–522, (2016).
- Amani, V., Safari, N. ve Khavasi, H.R., Synthesis, characterization and crystal structure determination of iron(III) hetero-ligand complexes containing 2,2’-bipyridine, 5,5’-dimethyl-2,2’-bipyridine and chloride, [Fe(bipy)Cl4][bipyH] and [Fe(dmbipy)2Cl2][FeCl4], Polyhedron, 26, 15, 4257–4262, (2007).
- Kaushal, R., Kumar, N., Awasthi, P. ve Nehra K., Syntheses, characterization, and antibacterial study of titanium complexes, Turkish Journal of Chemistry, 37, 6, 936-945, (2013).
- Yilmaz, İ., Synthesis, structural characterization, and thermal properties of octahedral diperchlorato complexes of copper(II) with the chelating 2-aminomethylpiperidine and 2-aminomethylpyridine ligands, Inorganic and Nano-Metal Chemistry, 53, 4, 333-339, (2023).
- Pusz, J. ve Nitka, B., Synthesis and physicochemical properties of the complexes of Co (II), Ni (II), and Cu (II) with chrysin, Microchemical Journal, 56, 3, 373-381, (1997).
- Halevas, E., Mitrakas, A., Mavroidi, B., Athanasiou, D., Gkika, P., Antoniou, K., Samaras, G., Lialiaris, E., Hatzidimitriou, A., Pantazaki, A., Koukourakis, M., Sagnou, M., Pelecanou, M. ve Lialiaris, T., Structurally characterized copper-chrysin complexes display genotoxic and cytotoxic activity in human cells, Inorganica Chimica Acta, 515, 120062, (2021).
- Roy, S., Sil, A. ve Chakraborty, T., Potentiating apoptosis and modulation of p53, Bcl2, and Bax by a novel chrysin ruthenium complex for effective chemotherapeutic efficacy against breast cancer, Journal of Cellular Physiology, 234, 4, 4888–4909, (2019).
- Dalal, A., Nehra, K., Hooda, A., Singh, D., Kumar, S. ve Malik, R.S., Synthesis, photophysical characteristics and geometry optimization of Tris(2-benzoylacetophenonate)europium complexes with 2,2′-Bipyridine derivatives, Journal of Luminescence, 247, 118873, (2022).
There are 28 citations in total.
Details
| Primary Language | Turkish |
|---|---|
| Subjects | Organic Chemistry (Other) |
| Journal Section | Research Articles |
| Authors | |
| Project Number | FHIZ-2021-440 |
| Early Pub Date | July 6, 2023 |
| Publication Date | July 7, 2023 |
| Submission Date | November 15, 2022 |
| Published in Issue | Year 2023 Volume: 25 Issue: 2 |