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Suda Çözünebilir Schiff Bazı Metal Komplekslerinin Sentezi ve Antikanser Aktivitesi

Yıl 2020, Cilt: 10 Sayı: 2, 441 - 454, 30.12.2020
https://doi.org/10.37094/adyujsci.738743

Öz

Bu çalışmada, 4-amino-3-hidroksinaftalin-1-sülfonik asit ve 2-hidroksi-3- metoksibenzaldehitten kondensasyon reaksiyonu ile S, O, N hetero atomları içeren suda çözünebilir bir Schiff Bazı elde edildi. Ek olarak, ligandın Cu (II), Zn (II) ve Ni (II) kompleksleri sentezlendi ve elementel analiz, manyetik duyarlılık ve FT-IR, H-NMR ve C-NMR gibi spektroskopik tekniklerle karakterize edildi. Ligandın ve üç metal kompleksinin A549 akciğer kanseri hücre hattında antikanser aktiviteleri değerlendirildi. L-Cu ve L-Zn olarak etiketlenmiş Bakır (II) ve Çinko (II) komplekslerinin IC50 değerleri sırasıyla 12 ve 80 μM olarak bulundu. L- Cu ve L-Zn komplekslerinin A549 hücrelerinde apoptozu indüklediği ve hücre göçünü inhibe ettiği görüldü. Ligand (L) ve Nikel (II) bileşiklerinin (L-Ni) A549 hücre proliferasyonu üzerinde herhangi bir etki göstermediği belirlendi.

Kaynakça

  • [1] Boghaei, D.M., Gharagozlou, M., Synthesis and characterization of novel water- soluble zinc (II) Schiff-base complexes derived from amino acids and salicylaldehyde-5- sulfonates, Journal of Coordination Chemistry, 60(3), 339-346, 2007.
  • [2] Hosseini-Yazdi, S.A., Mirzaahmadi, A., Khandar, A.A., Eigner, V., Dušek, M., Lotfipour, F., Mahdavi, M., Soltani, S., Dehghan, G., Synthesis, characterization and in vitro biological activities of new water-soluble copper (II), zinc (II), and nickel (II) complexes with sulfonato-substituted Schiff base ligand, Inorganica Chimica Acta, 458, 171-180, 2017.
  • [3] Hosseini-Yazdi, S.A., Mirzaahmadi, A., Khandar, A.A., Eigner, V., Dušek, M., Mahdavi, M., Soltani, S., Lotfipour, F., White, J., Reactions of copper (II), nickel (II), and zinc (II) acetates with a new water-soluble 4-phenylthiosemicarbazone Schiff base ligand: Synthesis, characterization, unexpected cyclization, antimicrobial, antioxidant, and anticancer activities, Polyhedron, 124, 156-165, 2017.
  • [4] Skorokhod, L.S., Seifullina, I.I., Minin, V.V., Vlasenko, V.G., Pirog, I.V., Synthesis and structure of Co (II), Ni (II), and Cu (II) complexes with Schiff bases, condensation products of 2-amino-4,8-naphthalenedisulfonic acid and aromatic carbinols, Russian Journal of Inorganic Chemistry, 52(7), 1006-1012, 2007.
  • [5] Atahan, A., Durmus, S., 1-Amino-2-hydroxy-4-naphthalenesulfonic acid based Schiff bases or naphtho[1,2-d]oxazoles: selective synthesis and photophysical properties, Spectrochim Acta A Mol Biomol Spectrosc, 144, 61-67, 2015.
  • [6] Mosmann, T., Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays, J. Immunol. Methods, 94(1-2), 57-63, 1983.
  • [7] https://www.biolegend.com/nl-be/products/apc-annexin-v-apoptosis-detection-kit- with-pi-9788
  • [8] Erdem, E., Sari, E.Y., Kilinçarslan, R., Kabay, N., Synthesis and characterization of azo-linked Schiff bases and their nickel (II), copper (II), and zinc (II) complexes, Transition Metal Chemistry, 34(2), 167-174, 2008.
  • [9] Tunçel, M., Serin, S., Synthesis and characterization of copper (ıı), nickel (ıı), and cobalt (ıı) chelates with tridentate schiff base ligands derived from 4-amino-5- hydroxynaphthalene-2,-7-disulfonic acid, synthesis and reactivity in ınorganic, Metal-Organic, and Nano-Metal Chemistry, 33(6), 985-998, 2003.
  • [10] Al-Sha’alan, N.H., Antimicrobial activity and spectral, magnetic and thermal studies of some transition metal complexes of a schiff base hydrazone containing a quinoline moiety, Molecules, 12, 1080-1091, 2007.
  • [11] Gönül, İ., Synthesis and structural characterization of ONO type tridentate ligands and their Co (II) and Ni (II) complexes: Investigation of electrical conductivity and antioxidant properties, Inorg. Chim. Acta, 495, 119027 (1-8), 2019.
  • [12] Kalanithi, M., Kodimunthiri, D., Rajarajan, M., Tharmaraj, P ., Synthesis, characterization and biological activity of some new VO (IV), Co (II), Ni (II), Cu (II) and Zn (II) complexes of chromone based NNO Schiff base derived from 2-aminothiazole, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 82, 290-298, 2011.
  • [13] Senthil, Raja, D., Ramachandran, E., Bhuvanesh, N.S.P., Natarajan, K., Synthesis, structure and in vitro pharmacological evaluation of a novel 2-oxo-1, 2-dihydroquinoline-3- carbaldehyde (2′-methylbenzoyl) hydrazone bridged copper (II) coordination polymer. European Journal of Medicinal Chemistry, 64, 148-159, 2013.
  • [14] Huang, K.B., Chen, Z.F., Liu, Y.C., Wang, M., Wei, J.H., Xie, X.L., Zhang, J.L., Hu K., Liang, H., Copper (II/I) complexes of 5-pyridin-2-yl-[1,3]dioxolo[4,5-g]isoquinoline: synthesis, crystal structure, antitumor activity and DNA interaction, European Journal of Medicinal Chemistry, 70, 640-648, 2013.
  • [15] Hejchman, E., Kruszewska, H., Maciejewska, D., Sowirka‐Taciak, B., Tomczyk M., Sztoksz‐Ignasiak A., Jankowski, J., Młynarczuk‐Biały, I., Design, synthesis, and biological activity of Schiff bases bearing salicyl and 7‐hydroxycoumarinyl moieties, Monatshefte für Chemie - Chemical Monthly, 155, 255-266, 2019.
  • [16] Barone, G., Terenzi, A., Lauria, A., Almerico, A.M., Leal, J.M., Busto, N., García, B., DNA-binding of nickel (II), copper (II) and zinc (II) complexes: Structure–affinity relationships, Coordination Chemistry Review, 257(19-20), 2848-2862, 2013.
  • [17] Mokhles, M.A., Ammar, A.L., Hanan, A.M, Samia, A.M., Mamdouh, M.A., Ahmed, A.R., Synthesis, anticancer activity and molecular docking study of Schiff base complexes containing thiazole moiety, Beni-Suef University Journal of Basic and Applied Sciences, 5, 85- 96, 2016.
  • [18] Tripathi, L.P., Kumar, Singhai, A.K., Role of chelates in treatment of cancer, Indian Journal of Cancer, 44(2), 62, 2007.

Synthesis and Anticancer Activities of Water Soluble Schiff Base Metal Complexes

Yıl 2020, Cilt: 10 Sayı: 2, 441 - 454, 30.12.2020
https://doi.org/10.37094/adyujsci.738743

Öz

In this study, we synthesized the water-soluble Schiff Base containing S, O, N heteroatoms by the condensation reaction from 4-amino-3-hydroxynaphthalene-1-sulfonic acid and 2- hydroxy-3-methoxybenzaldehyde. In addition, Cu (II), Zn (II) and Ni (II) complexes of the ligand were synthesized and characterized by elemental analysis, magnetic susceptibility and spectroscopic techniques such as FT-IR, H-NMR and C-NMR. The anticancer activities of ligand and its three metal complexes on A549 lung cancer cell lines were evaluated. Cell viability experiments revealed that Ligand (L) and nickel (II) complex (L-Ni) did not able to inhibit A549 cell proliferation while L-Cu and L-Zn had 12 and 80 μM of IC50 values respectively. These last two complexes also induced apoptosis and suppressed cell migration on A549 cells.

Kaynakça

  • [1] Boghaei, D.M., Gharagozlou, M., Synthesis and characterization of novel water- soluble zinc (II) Schiff-base complexes derived from amino acids and salicylaldehyde-5- sulfonates, Journal of Coordination Chemistry, 60(3), 339-346, 2007.
  • [2] Hosseini-Yazdi, S.A., Mirzaahmadi, A., Khandar, A.A., Eigner, V., Dušek, M., Lotfipour, F., Mahdavi, M., Soltani, S., Dehghan, G., Synthesis, characterization and in vitro biological activities of new water-soluble copper (II), zinc (II), and nickel (II) complexes with sulfonato-substituted Schiff base ligand, Inorganica Chimica Acta, 458, 171-180, 2017.
  • [3] Hosseini-Yazdi, S.A., Mirzaahmadi, A., Khandar, A.A., Eigner, V., Dušek, M., Mahdavi, M., Soltani, S., Lotfipour, F., White, J., Reactions of copper (II), nickel (II), and zinc (II) acetates with a new water-soluble 4-phenylthiosemicarbazone Schiff base ligand: Synthesis, characterization, unexpected cyclization, antimicrobial, antioxidant, and anticancer activities, Polyhedron, 124, 156-165, 2017.
  • [4] Skorokhod, L.S., Seifullina, I.I., Minin, V.V., Vlasenko, V.G., Pirog, I.V., Synthesis and structure of Co (II), Ni (II), and Cu (II) complexes with Schiff bases, condensation products of 2-amino-4,8-naphthalenedisulfonic acid and aromatic carbinols, Russian Journal of Inorganic Chemistry, 52(7), 1006-1012, 2007.
  • [5] Atahan, A., Durmus, S., 1-Amino-2-hydroxy-4-naphthalenesulfonic acid based Schiff bases or naphtho[1,2-d]oxazoles: selective synthesis and photophysical properties, Spectrochim Acta A Mol Biomol Spectrosc, 144, 61-67, 2015.
  • [6] Mosmann, T., Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays, J. Immunol. Methods, 94(1-2), 57-63, 1983.
  • [7] https://www.biolegend.com/nl-be/products/apc-annexin-v-apoptosis-detection-kit- with-pi-9788
  • [8] Erdem, E., Sari, E.Y., Kilinçarslan, R., Kabay, N., Synthesis and characterization of azo-linked Schiff bases and their nickel (II), copper (II), and zinc (II) complexes, Transition Metal Chemistry, 34(2), 167-174, 2008.
  • [9] Tunçel, M., Serin, S., Synthesis and characterization of copper (ıı), nickel (ıı), and cobalt (ıı) chelates with tridentate schiff base ligands derived from 4-amino-5- hydroxynaphthalene-2,-7-disulfonic acid, synthesis and reactivity in ınorganic, Metal-Organic, and Nano-Metal Chemistry, 33(6), 985-998, 2003.
  • [10] Al-Sha’alan, N.H., Antimicrobial activity and spectral, magnetic and thermal studies of some transition metal complexes of a schiff base hydrazone containing a quinoline moiety, Molecules, 12, 1080-1091, 2007.
  • [11] Gönül, İ., Synthesis and structural characterization of ONO type tridentate ligands and their Co (II) and Ni (II) complexes: Investigation of electrical conductivity and antioxidant properties, Inorg. Chim. Acta, 495, 119027 (1-8), 2019.
  • [12] Kalanithi, M., Kodimunthiri, D., Rajarajan, M., Tharmaraj, P ., Synthesis, characterization and biological activity of some new VO (IV), Co (II), Ni (II), Cu (II) and Zn (II) complexes of chromone based NNO Schiff base derived from 2-aminothiazole, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 82, 290-298, 2011.
  • [13] Senthil, Raja, D., Ramachandran, E., Bhuvanesh, N.S.P., Natarajan, K., Synthesis, structure and in vitro pharmacological evaluation of a novel 2-oxo-1, 2-dihydroquinoline-3- carbaldehyde (2′-methylbenzoyl) hydrazone bridged copper (II) coordination polymer. European Journal of Medicinal Chemistry, 64, 148-159, 2013.
  • [14] Huang, K.B., Chen, Z.F., Liu, Y.C., Wang, M., Wei, J.H., Xie, X.L., Zhang, J.L., Hu K., Liang, H., Copper (II/I) complexes of 5-pyridin-2-yl-[1,3]dioxolo[4,5-g]isoquinoline: synthesis, crystal structure, antitumor activity and DNA interaction, European Journal of Medicinal Chemistry, 70, 640-648, 2013.
  • [15] Hejchman, E., Kruszewska, H., Maciejewska, D., Sowirka‐Taciak, B., Tomczyk M., Sztoksz‐Ignasiak A., Jankowski, J., Młynarczuk‐Biały, I., Design, synthesis, and biological activity of Schiff bases bearing salicyl and 7‐hydroxycoumarinyl moieties, Monatshefte für Chemie - Chemical Monthly, 155, 255-266, 2019.
  • [16] Barone, G., Terenzi, A., Lauria, A., Almerico, A.M., Leal, J.M., Busto, N., García, B., DNA-binding of nickel (II), copper (II) and zinc (II) complexes: Structure–affinity relationships, Coordination Chemistry Review, 257(19-20), 2848-2862, 2013.
  • [17] Mokhles, M.A., Ammar, A.L., Hanan, A.M, Samia, A.M., Mamdouh, M.A., Ahmed, A.R., Synthesis, anticancer activity and molecular docking study of Schiff base complexes containing thiazole moiety, Beni-Suef University Journal of Basic and Applied Sciences, 5, 85- 96, 2016.
  • [18] Tripathi, L.P., Kumar, Singhai, A.K., Role of chelates in treatment of cancer, Indian Journal of Cancer, 44(2), 62, 2007.
Toplam 18 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Kimya
Yazarlar

Burcu Saygıdeğer Demir 0000-0001-5179-0522

İlyas Gönül 0000-0002-7697-3613

Gizem Gümüşgöz Çelik Bu kişi benim 0000-0003-4816-7419

Seda İpekbayrak Bu kişi benim 0000-0001-7628-807X

Yasemin Saygideger 0000-0003-3293-373X

Yayımlanma Tarihi 30 Aralık 2020
Gönderilme Tarihi 18 Mayıs 2020
Kabul Tarihi 11 Kasım 2020
Yayımlandığı Sayı Yıl 2020 Cilt: 10 Sayı: 2

Kaynak Göster

APA Saygıdeğer Demir, B., Gönül, İ., Gümüşgöz Çelik, G., İpekbayrak, S., vd. (2020). Synthesis and Anticancer Activities of Water Soluble Schiff Base Metal Complexes. Adıyaman University Journal of Science, 10(2), 441-454. https://doi.org/10.37094/adyujsci.738743
AMA Saygıdeğer Demir B, Gönül İ, Gümüşgöz Çelik G, İpekbayrak S, Saygideger Y. Synthesis and Anticancer Activities of Water Soluble Schiff Base Metal Complexes. ADYU J SCI. Aralık 2020;10(2):441-454. doi:10.37094/adyujsci.738743
Chicago Saygıdeğer Demir, Burcu, İlyas Gönül, Gizem Gümüşgöz Çelik, Seda İpekbayrak, ve Yasemin Saygideger. “Synthesis and Anticancer Activities of Water Soluble Schiff Base Metal Complexes”. Adıyaman University Journal of Science 10, sy. 2 (Aralık 2020): 441-54. https://doi.org/10.37094/adyujsci.738743.
EndNote Saygıdeğer Demir B, Gönül İ, Gümüşgöz Çelik G, İpekbayrak S, Saygideger Y (01 Aralık 2020) Synthesis and Anticancer Activities of Water Soluble Schiff Base Metal Complexes. Adıyaman University Journal of Science 10 2 441–454.
IEEE B. Saygıdeğer Demir, İ. Gönül, G. Gümüşgöz Çelik, S. İpekbayrak, ve Y. Saygideger, “Synthesis and Anticancer Activities of Water Soluble Schiff Base Metal Complexes”, ADYU J SCI, c. 10, sy. 2, ss. 441–454, 2020, doi: 10.37094/adyujsci.738743.
ISNAD Saygıdeğer Demir, Burcu vd. “Synthesis and Anticancer Activities of Water Soluble Schiff Base Metal Complexes”. Adıyaman University Journal of Science 10/2 (Aralık 2020), 441-454. https://doi.org/10.37094/adyujsci.738743.
JAMA Saygıdeğer Demir B, Gönül İ, Gümüşgöz Çelik G, İpekbayrak S, Saygideger Y. Synthesis and Anticancer Activities of Water Soluble Schiff Base Metal Complexes. ADYU J SCI. 2020;10:441–454.
MLA Saygıdeğer Demir, Burcu vd. “Synthesis and Anticancer Activities of Water Soluble Schiff Base Metal Complexes”. Adıyaman University Journal of Science, c. 10, sy. 2, 2020, ss. 441-54, doi:10.37094/adyujsci.738743.
Vancouver Saygıdeğer Demir B, Gönül İ, Gümüşgöz Çelik G, İpekbayrak S, Saygideger Y. Synthesis and Anticancer Activities of Water Soluble Schiff Base Metal Complexes. ADYU J SCI. 2020;10(2):441-54.

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