Research Article
Year 2020,
Volume: 10 Issue: 2, 441 - 454, 30.12.2020
Abstract
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.
References
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- [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.
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- [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.
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- [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.
Year 2020,
Volume: 10 Issue: 2, 441 - 454, 30.12.2020
Abstract
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.
References
- [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.
There are 18 citations in total.
Details
| Primary Language | English |
|---|---|
| Journal Section | Chemistry |
| Authors | |
| Publication Date | December 30, 2020 |
| Submission Date | May 18, 2020 |
| Acceptance Date | November 11, 2020 |
| Published in Issue | Year 2020 Volume: 10 Issue: 2 |
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