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Synthesis, Spectroscopic and Cytotoxic Properties of Zinc (II) and Cobalt (II) 4-Fluorobenzoate with 3-Hydroxypyridine Complexes

Year 2021, Volume: 8 Issue: 1, 14 - 26, 30.06.2021

Mustafa Sertçelik Giray Buğra Akbaba Füreya Elif Öztürkkan

Abstract

In this study, two complexes of Zn (II) and Co (II) metals were synthesized with 4-fluorobenzoic acid and 3-hydroxypyridine containing N-donor atom. The structure of the two complexes synthesized was characterized by elemental analysis and FT-IR spectroscopy. The cytotoxic properties of the complexes, whose structures are determined, at the concentration range of 62,5-500 ppm were investigated using the MTT method on lymphocyte cells.

Keywords

Zn complex Co complex 4-fluorobenzoic acid 3-hydroxypyridine MTT Cytotoxicity

References

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  • Aktaş Yokuş, Ö., Yüksek, H., Manap, S., Aytemiz, F., Alkan, M., Beytur, M., Gürsoy Kol, Ö. (2017). In-vitro biological activity of some new 1, 2, 4-triazole derivatives with their potentiometric titrations. Bulgarian Chemical Communications, 49(1), 98-106.
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  • Huseynova, MT., Aliyeva, MN., Medjidov, AA., Şahin, O., Yalçın, B., (2019). Cu (II) complex with thiosemicarbazone of glyoxylic acid as an anion ligand in a polymeric structure, Journal of Molecular Structure, 1176, 895-900.
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Kobalt(II) ve Çinko(II) 4-Florobenzoatın 3-Hidroksipiridin Komplekslerinin Sentezi, Spektroskopik ve Sitotoksik Özellikleri

Year 2021, Volume: 8 Issue: 1, 14 - 26, 30.06.2021

Mustafa Sertçelik Giray Buğra Akbaba Füreya Elif Öztürkkan

Abstract

References

  • Abdolmaleki, S., Ghadermazi, M., Ashengroph, M., Saffari, A., & Sabzkohi, S. M. (2018). Cobalt (II), zirconium(IV), calcium(II) complexes with dipicolinic acid and imidazole derivatives: X-ray studies, thermal analyses, evaluation as in vitro antibacterial and cytotoxic agents. Inorganica Chimica Acta, 480, 70–82. https://doi.org/10.1016/j.ica.2018.04.047
  • Adly, O. M., Shebl, M., Abdelrhman, E. M., & El-Shetary, B. A. (2020). Synthesis, spectroscopic, X-ray diffraction, antimicrobial and antitumor studies of Ni(II) and Co(II) complexes derived from 4-acetyl-5,6-diphenyl-3(2H)-pyridazinone and ethylenediamine. Journal of Molecular Structure, 1219, 128607. https://doi.org/10.1016/j.molstruc.2020.128607
  • Akbaba, G. B., & Ozturk, C. (2019). Investigation of Antibacterial and Cytotoxic Properties of Mix Ligand Complex of Zinc 2-Fluorobenzoate with Nicotinamide. Hittite Journal of Science & Engineering, 6(4), 269–274.
  • Aktaş Yokuş, Ö., Yüksek, H., Manap, S., Aytemiz, F., Alkan, M., Beytur, M., Gürsoy Kol, Ö. (2017). In-vitro biological activity of some new 1, 2, 4-triazole derivatives with their potentiometric titrations. Bulgarian Chemical Communications, 49(1), 98-106.
  • Arora, S., Talwar, D., Singh, M., Sahoo, S. C., & Sharma, R. (2020). Second sphere coordination in orthonitrophenolate binding: Synthesis, biological, cytotoxic and X-ray structural studies of [Co(bpy)2CO3](C6H4NO3)·3H2O. Journal of Molecular Structure, 1199, 127017. https://doi.org/10.1016/j.molstruc.2019.127017
  • Bahçeci, Ş., Yıldırım, N., Gürsoy Kol, Ö., Manap, S., Beytur, M., Yüksek, H., (2016). Synthesis, characterization and antioxidant properties of new 3-alkyl (aryl)-4-(3-hydroxy-4-methoxybenzylidenamino)-4,5-dihydro-1H-1, 2, 4-triazol-5-ones. Rasayan Journal of Chemistry, 9(3), 494-501.
  • Beytur, M., Turhan Irak, Z., Manap, S., Yüksek, H. (2019). Synthesis, characterization and theoretical determination of corrosion inhibitor activities of some new 4, 5-dihydro-1H-1, 2, 4-Triazol-5-one derivatives. Heliyon, 5(6), e01809.
  • Beytur, M., Avınca, I. (2021). Molecular, Electronic, Nonlinear Optical and Spectroscopic Analysis of Heterocyclic 3-Substituted-4-(3-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones: Experiment and DFT Calculations. Heterocyclic Communications, 27, 1-16.
  • Bhattacharyya, M. K., Gogoi, A., Chetry, S., Dutta, D., Verma, A. K., Sarma, B., ve ark. (2019). Antiproliferative evaluation and supramolecular association in Mn(II) and Zn(II) bipyridine complexes: Combined experimental and theoretical studies. Journal of Inorganic Biochemistry, 200, 110803. https://doi.org/10.1016/j.jinorgbio.2019.110803
  • Chowdhury, M. A., Huq, F., Abdullah, A., Beale, P., & Fisher, K. (2005). Synthesis, characterization and binding with DNA of four planaramineplatinum(II) complexes of the forms: trans-PtL2Cl2 and [PtL3Cl]Cl, where L=3-hydroxypyridine, 4-hydroxypyridine and imidazo(1,2-α)pyridine. Journal of Inorganic Biochemistry, 99(5), 1098–1112. https://doi.org/10.1016/j.jinorgbio.2005.02.002
  • Conte, L., Napoli, M., Gambaretto, G. P., Carlini, F. M., & Bonini, D. (1998). p-Fluorobenzaldehyde and p-fluorobenzoic acid by oxidation of p-fluorobenzyl derivatives. Journal of Fluorine Chemistry, 87(1), 19–23. https://doi.org/10.1016/S0022-1139(97)00105-X
  • Deb, J., Lakshman, T. R., Ghosh, I., Jana, S. S., & Paine, T. K. (2020). Mechanistic studies of in vitro anti-proliferative and anti-inflammatory activities of the Zn(II)-NSAID complexes of 1,10-phenanthroline-5,6-dione in MDA-MB-231 cells. Dalton Transactions, 49(32), 11375–11384. https://doi.org/10.1039/d0dt01721c
  • Feldman, D. L., Mogelesky, T. C. (1987). Use of Histopaque for isolating mononuclear cells from rabbit blood. Journal of Immunological Methods, 102(2), 243–249. doi:10.1016/0022-1759(87)90083-4
  • García Liñares, G., Parraud, G., Labriola, C., & Baldessari, A. (2012). Chemoenzymatic synthesis and biological evaluation of 2- and 3-hydroxypyridine derivatives against Leishmania mexicana. Bioorganic & Medicinal Chemistry, 20(15), 4614–4624. https://doi.org/10.1016/j.bmc.2012.06.028
  • Hassan, A. M., Heakal, B. H., Said, A. O., Aboulthana, W. M., & Abdelmoaz, M. A. (2020). Comparative Study for Synthesis of Novel Mn (II), Co (II), Ni (II), Cu (II), Zn (II) and Zr (IV) Complexes under Conventional Methods and Microwave Irradiation and Evaluation of their Antimicrobial and Anticancer Activity. Egyptian Journal of Chemistry, 63(7), 2533–2550. https://doi.org/10.21608/ejchem.2020.21048.2255
  • Huq, F., Daghriri, H., Yu, J. Q., Beale, P., & Fisher, K. (2004). Studies on the synthesis and characterization of four trans-planaramineplatinum(II) complexes of the form trans-PtL(NH3)CL2 where L = 2-hydroxypyridine, 3-hydroxypyridine, imidazole, and imidazo(1,2-α)pyridine. European Journal of Medicinal Chemistry, 39(8), 691–697. https://doi.org/10.1016/j.ejmech.2004.04.005
  • Huq, F., Tayyem, H., Beale, P., & Yu, J. Q. (2007). Studies on the activity of three palladium(II) compounds of the form: Trans-PdL2Cl2 where L=2-hydroxypyridine, 3-hydroxypyridine, and 4-hydroxypyridine. Journal of Inorganic Biochemistry, 101(1), 30–35. https://doi.org/10.1016/j.jinorgbio.2006.08.001
  • Huseynova, M., Farzaliyev,V., Medjidov, A., Aliyeva, M., Taslimi, P., Sahin, O., Yalçın B. (2020). Novel zinc compound with thiosemicarbazone of glyoxylic acid: Synthesis, crystal structure, and bioactivity properties, Journal of Molecular Structure, 1200, 127082.
  • Huseynova, MT., Aliyeva, MN., Medjidov, AA., Şahin, O., Yalçın, B., (2019). Cu (II) complex with thiosemicarbazone of glyoxylic acid as an anion ligand in a polymeric structure, Journal of Molecular Structure, 1176, 895-900.
  • Jaafar, A., Fix-Tailler, A., Mansour, N., Allain, M., Shebaby, W. N., Faour, W. H., ve ark. (n.d.). Synthesis, characterization, antifungal and antibacterial activities evaluation of copper (II), zinc (II) and cadmium (II) chloride and bromide complexes with new (E)-1-(3,4-dimethoxybenzylidene)-4-methylthiosemicarbazone ligand. Applied Organometallic Chemistry, e5988. https://doi.org/10.1002/aoc.5988
  • Kammula, U. S., Lee, K. H., Riker, A. I., Wang, E., Ohnmacht, G. A., Rosenberg, S. A., Marincola, F. M. (1999). Functional Analysis of Antigen-Specific T Lymphocytes by Serial Measurement of Gene Expression in Peripheral Blood Mononuclear Cells and Tumor Specimens. The Journal of Immunology, 163(12) 6867-6875.
  • Kumar, S. B., Mahendrasinh, Z., Ankita, S., Mohammedayaz, R., Pragna, P., & Suresh, E. (2012). A binuclear chloride bridged copper(II) complex with a modified ligand structure and different coordination environment and mononuclear cobalt(II) complexes with a pyridylpyrazole ligand: Synthesis, structure and cytotoxic activity. Polyhedron, 36(1), 15–20. https://doi.org/10.1016/j.poly.2012.01.019
  • Kreienborga, N.M. and Merten, C., (2019). How to treat C–F stretching vibrations? A vibrational CD study on chiral fluorinated molecules. Phys. Chem. Chem. Phys.;,21, 3506-3511. https://doi.org/10.1039/C8CP02395F
  • Krishnakumar, V., Dheivamalar S., Xavier, R. J., Balachandran, V. (2006). Analysis of vibrational spectra of 4-amino-2,6-dichloropyridine and 2-chloro-3,5-dinitropyridine based on density functional theory calculations. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; 65(1), 147-154. https://doi.org/10.1016/j.saa.2005.09.039
  • Liguori, P. F., Valentini, A., Palma, M., Bellusci, A., Bernardini, S., Ghedini, M., ve ark. (2010). Non-classical anticancer agents: synthesis and biological evaluation of zinc(ii) heteroleptic complexes. Dalton Transactions, 39(17), 4205. https://doi.org/10.1039/b922101h
  • Mobinikhaledi, A., Forughifar, N., Shariatzadeh, S. M., & Fallah, M. (2006). Synthesis and antibacterial activity of some N-(3-hydroxy-2pyridyl) benzamides. Heterocyclic Communications, 12(6), 427–430.
  • Mjos, K. D.and Orvig, C. (2014). Metallodrugs in medicinal inorganic chemistry. Chemical Reviews, 114(8), 4540–4563. https://doi.org/10.1021/cr400460s
  • Nakamoto, K. (2006). Infrared and Raman Spectra of Inorganic and Coordination Compounds. In Handbook of Vibrational Spectroscopy. American Cancer Society. https://doi.org/10.1002/0470027320.s4104
  • Nashre-ul-Islam, S. Mohd., Dutta, D., Verma, A. K., Nath, H., Frontera, A., Sharma, P., & Bhattacharyya, M. K. (2019). Antiproliferative evaluation and supramolecular association involving electrostatically enhanced π-π interaction in isostructural coordination solids of Mn(II), Co(II) and Zn(II) chlorobenzoates: Experimental and theoretical studies. Inorganica Chimica Acta, 498, 119161. https://doi.org/10.1016/j.ica.2019.119161
  • Necefoğlu, H., Özbek, F. E., Öztürk, V., Tercan, B., & Hökelek, T. (2011). Bis­(4-fluoro­benzoato)-κ2 O,O′;κO-(4-fluoro­benzoic acid-κO)bis­(nico­tinamide-κN1)copper(II). Acta Crystallographica Section E: Structure Reports Online, 67(Pt 7), m887–m888. https://doi.org/10.1107/S1600536811020897
  • Ozbek, F. E., Sertcelik, M., Yuksek, M., Kucukoz, B., Elmali, A., & Sahin, E. (2019). Two new potential optical materials: Co(II) and Ni(II) 3-fluorobenzoate complexes with pyridine-3-carboxamide. Journal of Coordination Chemistry, 72(5–7), 786–795. https://doi.org/10.1080/00958972.2019.1590560
  • Pavia D. L., Lampman G. M., Kriz G. S. (2001). Introduction to spectroscopy: a guide for students of organic chemistry (3. ed.). South Melbourne: Brooks/Cole.
  • Pucci, D., Crispini, A., Mendiguchía, B. S., Pirillo, S., Ghedini, M., Morelli, S., & De Bartolo, L. (2013). Improving the bioactivity of Zn(ii)-curcumin based complexes. Dalton Transactions, 42(26), 9679. https://doi.org/10.1039/c3dt50513h
  • Sertcelik, M., & Durman, M. (2020). Synthesis, Characterization, and Antibacterial Activity of Cd(II) Complexes with 3-/4-Fluorobenzoates and 3-Hydroxypiridine as Co-Ligands. Russian Journal of Inorganic Chemistry, 65(9), 1351–1359. https://doi.org/10.1134/S0036023620090168
  • Sertcelik, M., Ozbek, F. E., Yuksek, M., Elmali, A., Aydogdu, O., Necefoglu, H., & Hokelek, T. (2020). Synthesis, spectral, thermal, structural, optical characterization, and Hirshfield surface analysis of N,N’-diethylnicotinamide complexes of Mn(II) and Co(II) 4-cyanobenzoates. Chemical Papers, 74(6), 2021–2033. https://doi.org/10.1007/s11696-019-01040-0
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There are 40 citations in total.

Details

Primary Language Turkish
Subjects Environmental Sciences
Journal Section Caucasian Journal of Science
Authors

Mustafa Sertçelik 0000-0001-7919-7907

Giray Buğra Akbaba 0000-0002-1413-9498

Füreya Elif Öztürkkan 0000-0001-6376-4161

Publication Date June 30, 2021
Submission Date March 14, 2021
Acceptance Date June 30, 2021
Published in Issue Year 2021 Volume: 8 Issue: 1

Cite

APA Sertçelik, M., Akbaba, G. B., & Öztürkkan, F. E. (2021). Kobalt(II) ve Çinko(II) 4-Florobenzoatın 3-Hidroksipiridin Komplekslerinin Sentezi, Spektroskopik ve Sitotoksik Özellikleri. Caucasian Journal of Science, 8(1), 14-26.
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