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Synthesis, characterization and in vitro cytotoxic activity of platinum(II) oxalato complexes involving 2-substitutedimidazole or 2-substitutedbenzimidazole derivatives as carrier ligands

Year 2023, , 308 - 313, 28.12.2023

Emine Merve Ertuğrul , Azime Berna Özçelik , Nebahat Aytuna Çerçi , Leyla Açık , Semra Utku

https://doi.org/10.26650/IstanbulJPharm.2023.1266118

Abstract

Background and Aims: Cisplatin is currently one of the most widely used anticancer drugs in the world. However, its clinical usefulness has frequently been limited by severe side effects, such as nephrotoxicity, ototoxicity and neurotoxicity. Therefore, platinum(II) oxalato complexes with substitute imidazole or benzimidazole carrier ligands were synthesized and their cytotoxic effects were investigated against non-small cell lung cancer (H1299) and human colon adenocarcinoma (CaCo-2), and mouse fibroblast cells lines (L929).

Methods: Four platinum(II) complexes, [Pt(L1-L4)2(oxalate)] were synthesized and characterized by FT-IR, 1H NMR and elemental analyses. The MTT method was used to determine the potential antiproliferative effect of synthesized platinum(II) complexes and positive controls.

Results: In this study, the cytotoxic activity of platinum(II) complexes against tested cell lines was assessed, with moderate IC50 values. According to IC50 values, Complex 5 with 2-ethylbenzimidazole ligand was found to be the most active complex against H1299 and CaCo-2 cell lines. In general, the compounds are also promising drug candidates for H1299 cell lines with very low activity against the CaCo-2 cell lines.

Conclusion: Further modification and development of Complex 4 and 5 derivatives and in vitro cytotoxic activity studies against different cancer cell lines may lead to the emergence of new anticancer agents in the near future.

Keywords

Cytotoxic activity 2-ethylbenzimidazole 2-methylbenzimidazole 2-phenylimidazole platinum(II) complexes

Supporting Institution

Mersin University Scientific Research Fund

Project Number

2018-1-TP2-2783

References

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  • Dasari, S., & Tchounwou, P.B. (2014). Cisplatin in cancer therapy: Molecular mechanism of action. European Journal of Pharmacol-ogy, 740, 364-378. https://doi.org/10.1016/j.ejphar.2014.07.025 google scholar
  • Deo, K.M., Ang, D.L., McGhie, B., Rajamanickam, A., Dhi-man, A., Khoury A., . . . Aldrich-Wright, J.R. (2018). Platinum coordination compounds with potent anticancer activity. Coordination Chemistry Reviews, 375, 148-163. https://doi.org/10.1016/j.ccr.2017.11.014 google scholar
  • Diamond, E., Molina, A.M., Carbonaro, M., Akhtar, N. H., Giannakakou, P., Tagawa, S.T., & Nanus, D.M. (2015). Cytotoxic chemotherapy in the treatment of ad-vanced renal cell carcinoma in the era of targeted ther-apy. Critical Reviews Oncology/Hematology. 96(3), 518-526. https://doi.org/10.1016/j.critrevonc.2015.08.007 google scholar
  • Gözelle, M., Süloğlu, A.K., Selmanoglu, G., Ramazanoğlu, N., Açık, L., & Gümüş, F. (2019). Studies on the synthesis, characteriza-tion, cytotoxic activities and plasmid DNA binding of platinum(II) complexes having 2-subsituted benzimidazole ligands. Polyhe-dron, 161, 298-308. https://doi.org/10.1016/j.poly.2019.01.028 google scholar
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  • Özçelik, A.B., Utku, S., Gümüş, F., Çelebi Keskin, A., Açık, L., Yılmaz, Ş., & Özgüngör A. (2012). Cytotox-icity and DNA interactions of some platinum(II) com-plexes with substituted benzimidazole ligands. Journal of En-zyme Inhibition and Medicinal Chemistry, 27(3), 413-418. https://doi.org/10.3109/14756366.2011.594046 google scholar
  • Özçelik, A.B., Gümüş, F., Sağkan, R.I., & Muşabak, U. (2015). Synthesis of platinum (II) complexes of 2-cycloalkyl-substituted benzimidazoles and their cytotoxic effects. Zeitschrift fur Naturforschung. C, Journal of Biosciences, 70(9-10), 243-250. https://doi.org/10.1515/znc-2014-4188 google scholar
  • Özçelik, A.B., Kılıç Süloğlu, A., Selmanoğlu, G., & Gümüş, F. (2019). Cytotoxic activity studies of some platinum(II) complexes with 2-substituted benzimidazole ligands. Revue Roumaine de Chimie, 64(9), 829-834. Retrieved from http://revroum.lew.ro/ google scholar
  • Peng, K., Liang, B.B., Liu, W., & Mao, Z.W. (2021). What blocks more anticancer platinum complexes from experiment to clinic: Major problems and potential strategies from drug de-sign perspectives. Coordination Chemistry Reviews, 449, 214210. https://doi.org/10.1016/j.ccr.2021.214210 google scholar
  • Perego, P., & Robert, J. (2016). Oxaliplatin in the era of personalized medicine: from mechanistic studies to clin-ical efficacy. Cancer Chemotherapy and Pharmacology. 77(1), 5-18. doi:10.1007/s00280-015-2901-x hillips, M. A. (1928). CCCXVII.—the formation of 2-substituted benz-iminazoles. Journal of The Chemical Society, 2393-2399. https://doi.org/10.1039/jr9280002393 google scholar
  • Rabiger, D.J., & Joullie, M.M. (1964). The ionization constants, ultraviolet and infrared spectra of some substituted benzimi-dazoles. The Journal of Organic Chemistry, 29(2), 476-482. https://doi.org/10.1021/jo01025a502 google scholar
  • Salahuddin, Shaharyar, M., & Mazumder, A. (2017). Benzimidazoles: A biologically active compounds. Arabian Journal of Chemistry, 10(1), S157-S173. https://doi.org/10.1016/j.arabjc.2012.07.017 google scholar
  • Spingler, B., Whittington, D.A., & Lippard, S.J. (2001). 2.4 Â crystal structure of an oxaliplatin 1,2-d(GpG) Intrastrand cross-link in a DNA dodecamer duplex. Inorganic Chemistry, 40(22), 5596-5602. https://doi.org/10.1021/ic010790t google scholar
  • Starha, P., Trâvnfcek, Z., & Popa, I. (2010). Platinum(II) oxalato complexes with adenine-based carrier ligands showing significant in vitro antitumor activity. Journal of Inorganic Biochemistry, 104(6), 639-647. https://doi.org/10.1016/j.jinorgbio.2010.02.005 google scholar
  • Sundberg, R., & Martin, R.B. (1974). Interactions of histidine and other imidazole derivatives with transition metal ions in chem-ical and biological systems. Chemical Reviews, 74(4), 471. https://doi.org/10.1021/cr60290a003 google scholar
  • Sung, H., Ferlay, J., Siegel, R. L., Laversanne, M., Soerjomataram, I., Jemal, A., & Bray, F. (2021). Global cancer statistics 2020: Globocan estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA: A Cancer Journal for Clinicians, 71(3), 209-249. https://doi.org/10.3322/caac.21660 google scholar
  • Szulmanowicz, M.S., Zawartka, W., Gniewek, A., & Trzeciak, AM., (2010). Structure, dynamics and catalytic activity of palladium(II) complexes with imidazole ligands. Inorganica Chimica Acta, 363(15), 4346-4354. https://doi.org/10.1016/j.ica.2010.08.037 google scholar
  • Tarı, Ö., Gümüş, F., Açık, L., & Aydın, B. (2017). Synthesis, char-acterization and DNA binding studies of platinum(II) complexes with benzimidazole derivative ligands. Bioorganic Chemistry, 74, 272-283. https://doi.org/10.1016/j.bioorg.2017.08.015 google scholar
  • Todd, R. C., & Lippard, S. J. (2009). Inhibition of transcription by platinum antitumor compounds. Metallomics, 1(4), 280-291. https://doi.org/10.1039/b907567d google scholar
  • Utku, S., Topal, M, Döğen, A., & Serin, M.S. (2010). Syn-thesis, characterization, antibacterial and antifungal eval-uation of some new platinum (II) complexes of 2-phenylbenzimidazole ligands. Turkish Journal of Chemistry, 34, 427-436. https://doi.org/10.3906/kim-1002-5 google scholar
  • Utku, S., Özcelik, A.B., Gümüş, F., Yılmaz, Ş., Arsoy, T., Açık, L., & Çelebi, K. A. (2014). Synthesis, in vitro cytotoxic activity and DNA interactions of new dicarboxylatoplatinum(II) com-plexes with 2-hydroxymethylbenzimidazole as carrier ligands. Journal of Pharmacy and Pharmacology, 66(11), 1593-1605. https://onlinelibrary.wiley.com/doi/full/10.1111/jphp.12290 google scholar
  • Wang, H., Wang, F., Tao, X., & Cheng, H. (2012). Ammonia-containing dimethyl sulfoxide: An improved solvent for the disso-lution of formazan crystals in the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. Analytical Biochem-istry, 421(1), 324-326. https://doi.org/10.1016/j.ab.2011.10.043 google scholar
  • Wright, J.B. (1951). The chemistry of benzimidazoles. Chemical Re-views, 48(3), 397-541. https://doi.org/10.1021/cr60151a002 google scholar
  • Wu, Y., Pradhan, P., Havener, J., Boysen, G., Swenberg, J. A., Camp-bell, S. L., & Chaney, S. G. (2004). NMR solution structure of an oxaliplatin 1,2-d(GG) Intrastrand Cross-link in a DNA dode-camer duplex. Journal of Molecular Biology, 341(5), 1251-1269. https://doi.org/10.1016/j.jmb.2004.06.066 google scholar
  • Zivkovic, M. D., Rajkovic, S., & Djuran, M. I. (2008). Re-action of [pt(gly-gly-N,N,o)i] with the N-acetylated dipep-tide L-methionyl-L-histidine: Selective platination of the his-tidine side chain by intramolecular migration of the plat-inum(II) complex. Bioorganic Chemistry, 36(3), 161-164. https://doi.org/10.1016/j.bioorg.2008.02.005 google scholar

Year 2023, , 308 - 313, 28.12.2023

Emine Merve Ertuğrul , Azime Berna Özçelik , Nebahat Aytuna Çerçi , Leyla Açık , Semra Utku

https://doi.org/10.26650/IstanbulJPharm.2023.1266118

Abstract

Project Number

2018-1-TP2-2783

References

  • Ali, I., Lone, M.N., & Aboul-Enein, H.Y. (2017). Imidazoles as po-tential anticancer agents. Medicinal Chemistry Communications, 8(9), 1742-1773. https://doi.org/10.1039/c7md00067g google scholar
  • Boğatarkan, C., Utku, S., & Açık, L. (2015). Synthesis, character-ization and pBR322 plasmid DNA interaction of platinum(II) complexes with imidazole and 2-phenylimidazole as carrier lig-ands. Revue Roumaine de Chimie, 60(1), 59-64. Retrieved from https://revroum.lew.ro/ google scholar
  • Burger, H., Loos, W.J., Eechoute, K., Verweij, J., Mathi-jssen, R. H. J., & Wiemer, E. A. C. (2011). Drug trans-porters of platinum-based anticancer agents and their clin-ical significance. Drug Resistance Updates, 14(1), 22-34. https://doi.org/10.1016/j.drup.2010.12.002 google scholar
  • Dasari, S., & Tchounwou, P.B. (2014). Cisplatin in cancer therapy: Molecular mechanism of action. European Journal of Pharmacol-ogy, 740, 364-378. https://doi.org/10.1016/j.ejphar.2014.07.025 google scholar
  • Deo, K.M., Ang, D.L., McGhie, B., Rajamanickam, A., Dhi-man, A., Khoury A., . . . Aldrich-Wright, J.R. (2018). Platinum coordination compounds with potent anticancer activity. Coordination Chemistry Reviews, 375, 148-163. https://doi.org/10.1016/j.ccr.2017.11.014 google scholar
  • Diamond, E., Molina, A.M., Carbonaro, M., Akhtar, N. H., Giannakakou, P., Tagawa, S.T., & Nanus, D.M. (2015). Cytotoxic chemotherapy in the treatment of ad-vanced renal cell carcinoma in the era of targeted ther-apy. Critical Reviews Oncology/Hematology. 96(3), 518-526. https://doi.org/10.1016/j.critrevonc.2015.08.007 google scholar
  • Gözelle, M., Süloğlu, A.K., Selmanoglu, G., Ramazanoğlu, N., Açık, L., & Gümüş, F. (2019). Studies on the synthesis, characteriza-tion, cytotoxic activities and plasmid DNA binding of platinum(II) complexes having 2-subsituted benzimidazole ligands. Polyhe-dron, 161, 298-308. https://doi.org/10.1016/j.poly.2019.01.028 google scholar
  • Grimmett, M.R. (1970). Advances in imidazole chem-istry. Advances in Heterocyclic Chemistry, 12, 103-183. https://doi.org/10.1016/S0065-2725(08)60973-3 google scholar
  • Gümüş, F., Algül, Ö., Eren, G., Eroğlu, H., Diril, N., Gür, S., & Özkul, A. (2003). Synthesis, cytotoxic activity on MCF-7 cell line and mutagenic activity of platinum(II) complexes with 2-substituted benzimidazole ligands. European Journal of Medic-inal Chemistry, 38(5), 473-480. https://doi.org/10.1016/s0223-5234(03)00058-8 google scholar
  • Gümüş, F., Eren, G., Açık, L., Çelebi, A., Öztürk, F., Yılmaz, Ş., . . . Elerman, Y. (2009). Synthesis, cytotoxity and DNA interac-tion of new cisplatin analogues containing substituted benzimida-zole ligands. Journal of Medicinal Chemistry, 52(5), 1345-1357. https://doi.org/10.1021/jm8000983 google scholar
  • Ho, G.Y., Woodward, N., & Coward, J.I. (2016). Cisplatin versus carboplatin: comparative review of therapeutic management in solid malignancies. Critical Reviews Oncology/Hematology. 102, 37-46. https://doi.org/10.1016/j.critrevonc.2016.03.014 google scholar
  • Iakovidis, A., Hadjiliadis, N. (1994). Complex compounds of platinum(II) and (IV) with amino acids, peptides and their derivatives. Coordination Chemistry Reviews. 135-136, 17-63. https://doi.org/10.1016/0010-8545(94)80064-2 google scholar
  • Manocha, P., Wakode, S.R., Kaur, A., Anand, K., & Kumar, H. (2016). A review: Imidazole synthesis and its bio-logical activities. International Journal of Pharmaceuti-cal Sciences and Research, 1(7), 12-16. Retrieved from: https://www.pharmacyjournal.net/archives/2016/vol1/issue7/1-7-16 google scholar
  • Navarro-Ranninger, C., Zamora, F., Alfonson Martmez-Cruz, L., Isea, R., & Masaguer, J. R. (1996). Synthesis and NMR structural anal-ysis of several orthopalladated complexes of substituted benzo-imidazole, -oxazole and -thiazole and study of two polymorphic crystals. Journal of Organometallic Chemistry, 518(1-2), 29-36. https://doi.org/10.1016/0022-328x(96)06218-3 google scholar
  • Özçelik, A.B., Utku, S., Gümüş, F., Çelebi Keskin, A., Açık, L., Yılmaz, Ş., & Özgüngör A. (2012). Cytotox-icity and DNA interactions of some platinum(II) com-plexes with substituted benzimidazole ligands. Journal of En-zyme Inhibition and Medicinal Chemistry, 27(3), 413-418. https://doi.org/10.3109/14756366.2011.594046 google scholar
  • Özçelik, A.B., Gümüş, F., Sağkan, R.I., & Muşabak, U. (2015). Synthesis of platinum (II) complexes of 2-cycloalkyl-substituted benzimidazoles and their cytotoxic effects. Zeitschrift fur Naturforschung. C, Journal of Biosciences, 70(9-10), 243-250. https://doi.org/10.1515/znc-2014-4188 google scholar
  • Özçelik, A.B., Kılıç Süloğlu, A., Selmanoğlu, G., & Gümüş, F. (2019). Cytotoxic activity studies of some platinum(II) complexes with 2-substituted benzimidazole ligands. Revue Roumaine de Chimie, 64(9), 829-834. Retrieved from http://revroum.lew.ro/ google scholar
  • Peng, K., Liang, B.B., Liu, W., & Mao, Z.W. (2021). What blocks more anticancer platinum complexes from experiment to clinic: Major problems and potential strategies from drug de-sign perspectives. Coordination Chemistry Reviews, 449, 214210. https://doi.org/10.1016/j.ccr.2021.214210 google scholar
  • Perego, P., & Robert, J. (2016). Oxaliplatin in the era of personalized medicine: from mechanistic studies to clin-ical efficacy. Cancer Chemotherapy and Pharmacology. 77(1), 5-18. doi:10.1007/s00280-015-2901-x hillips, M. A. (1928). CCCXVII.—the formation of 2-substituted benz-iminazoles. Journal of The Chemical Society, 2393-2399. https://doi.org/10.1039/jr9280002393 google scholar
  • Rabiger, D.J., & Joullie, M.M. (1964). The ionization constants, ultraviolet and infrared spectra of some substituted benzimi-dazoles. The Journal of Organic Chemistry, 29(2), 476-482. https://doi.org/10.1021/jo01025a502 google scholar
  • Salahuddin, Shaharyar, M., & Mazumder, A. (2017). Benzimidazoles: A biologically active compounds. Arabian Journal of Chemistry, 10(1), S157-S173. https://doi.org/10.1016/j.arabjc.2012.07.017 google scholar
  • Spingler, B., Whittington, D.A., & Lippard, S.J. (2001). 2.4 Â crystal structure of an oxaliplatin 1,2-d(GpG) Intrastrand cross-link in a DNA dodecamer duplex. Inorganic Chemistry, 40(22), 5596-5602. https://doi.org/10.1021/ic010790t google scholar
  • Starha, P., Trâvnfcek, Z., & Popa, I. (2010). Platinum(II) oxalato complexes with adenine-based carrier ligands showing significant in vitro antitumor activity. Journal of Inorganic Biochemistry, 104(6), 639-647. https://doi.org/10.1016/j.jinorgbio.2010.02.005 google scholar
  • Sundberg, R., & Martin, R.B. (1974). Interactions of histidine and other imidazole derivatives with transition metal ions in chem-ical and biological systems. Chemical Reviews, 74(4), 471. https://doi.org/10.1021/cr60290a003 google scholar
  • Sung, H., Ferlay, J., Siegel, R. L., Laversanne, M., Soerjomataram, I., Jemal, A., & Bray, F. (2021). Global cancer statistics 2020: Globocan estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA: A Cancer Journal for Clinicians, 71(3), 209-249. https://doi.org/10.3322/caac.21660 google scholar
  • Szulmanowicz, M.S., Zawartka, W., Gniewek, A., & Trzeciak, AM., (2010). Structure, dynamics and catalytic activity of palladium(II) complexes with imidazole ligands. Inorganica Chimica Acta, 363(15), 4346-4354. https://doi.org/10.1016/j.ica.2010.08.037 google scholar
  • Tarı, Ö., Gümüş, F., Açık, L., & Aydın, B. (2017). Synthesis, char-acterization and DNA binding studies of platinum(II) complexes with benzimidazole derivative ligands. Bioorganic Chemistry, 74, 272-283. https://doi.org/10.1016/j.bioorg.2017.08.015 google scholar
  • Todd, R. C., & Lippard, S. J. (2009). Inhibition of transcription by platinum antitumor compounds. Metallomics, 1(4), 280-291. https://doi.org/10.1039/b907567d google scholar
  • Utku, S., Topal, M, Döğen, A., & Serin, M.S. (2010). Syn-thesis, characterization, antibacterial and antifungal eval-uation of some new platinum (II) complexes of 2-phenylbenzimidazole ligands. Turkish Journal of Chemistry, 34, 427-436. https://doi.org/10.3906/kim-1002-5 google scholar
  • Utku, S., Özcelik, A.B., Gümüş, F., Yılmaz, Ş., Arsoy, T., Açık, L., & Çelebi, K. A. (2014). Synthesis, in vitro cytotoxic activity and DNA interactions of new dicarboxylatoplatinum(II) com-plexes with 2-hydroxymethylbenzimidazole as carrier ligands. Journal of Pharmacy and Pharmacology, 66(11), 1593-1605. https://onlinelibrary.wiley.com/doi/full/10.1111/jphp.12290 google scholar
  • Wang, H., Wang, F., Tao, X., & Cheng, H. (2012). Ammonia-containing dimethyl sulfoxide: An improved solvent for the disso-lution of formazan crystals in the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. Analytical Biochem-istry, 421(1), 324-326. https://doi.org/10.1016/j.ab.2011.10.043 google scholar
  • Wright, J.B. (1951). The chemistry of benzimidazoles. Chemical Re-views, 48(3), 397-541. https://doi.org/10.1021/cr60151a002 google scholar
  • Wu, Y., Pradhan, P., Havener, J., Boysen, G., Swenberg, J. A., Camp-bell, S. L., & Chaney, S. G. (2004). NMR solution structure of an oxaliplatin 1,2-d(GG) Intrastrand Cross-link in a DNA dode-camer duplex. Journal of Molecular Biology, 341(5), 1251-1269. https://doi.org/10.1016/j.jmb.2004.06.066 google scholar
  • Zivkovic, M. D., Rajkovic, S., & Djuran, M. I. (2008). Re-action of [pt(gly-gly-N,N,o)i] with the N-acetylated dipep-tide L-methionyl-L-histidine: Selective platination of the his-tidine side chain by intramolecular migration of the plat-inum(II) complex. Bioorganic Chemistry, 36(3), 161-164. https://doi.org/10.1016/j.bioorg.2008.02.005 google scholar
There are 34 citations in total.

Details

Primary Language English
Subjects Pharmacology and Pharmaceutical Sciences
Journal Section Original Article
Authors

Emine Merve Ertuğrul 0000-0003-0580-9581

Azime Berna Özçelik 0000-0002-3160-5753

Nebahat Aytuna Çerçi 0000-0002-7864-7213

Leyla Açık 0000-0002-3672-8429

Semra Utku 0000-0003-3181-9134

Project Number 2018-1-TP2-2783
Publication Date December 28, 2023
Submission Date March 24, 2023
Published in Issue Year 2023

Cite

APA Ertuğrul, E. M., Özçelik, A. B., Çerçi, N. A., Açık, L., et al. (2023). Synthesis, characterization and in vitro cytotoxic activity of platinum(II) oxalato complexes involving 2-substitutedimidazole or 2-substitutedbenzimidazole derivatives as carrier ligands. İstanbul Journal of Pharmacy, 53(3), 308-313. https://doi.org/10.26650/IstanbulJPharm.2023.1266118
AMA Ertuğrul EM, Özçelik AB, Çerçi NA, Açık L, Utku S. Synthesis, characterization and in vitro cytotoxic activity of platinum(II) oxalato complexes involving 2-substitutedimidazole or 2-substitutedbenzimidazole derivatives as carrier ligands. iujp. December 2023;53(3):308-313. doi:10.26650/IstanbulJPharm.2023.1266118
Chicago Ertuğrul, Emine Merve, Azime Berna Özçelik, Nebahat Aytuna Çerçi, Leyla Açık, and Semra Utku. “Synthesis, Characterization and in Vitro Cytotoxic Activity of platinum(II) Oxalato Complexes Involving 2-Substitutedimidazole or 2-Substitutedbenzimidazole Derivatives As Carrier Ligands”. İstanbul Journal of Pharmacy 53, no. 3 (December 2023): 308-13. https://doi.org/10.26650/IstanbulJPharm.2023.1266118.
EndNote Ertuğrul EM, Özçelik AB, Çerçi NA, Açık L, Utku S (December 1, 2023) Synthesis, characterization and in vitro cytotoxic activity of platinum(II) oxalato complexes involving 2-substitutedimidazole or 2-substitutedbenzimidazole derivatives as carrier ligands. İstanbul Journal of Pharmacy 53 3 308–313.
IEEE E. M. Ertuğrul, A. B. Özçelik, N. A. Çerçi, L. Açık, and S. Utku, “Synthesis, characterization and in vitro cytotoxic activity of platinum(II) oxalato complexes involving 2-substitutedimidazole or 2-substitutedbenzimidazole derivatives as carrier ligands”, iujp, vol. 53, no. 3, pp. 308–313, 2023, doi: 10.26650/IstanbulJPharm.2023.1266118.
ISNAD Ertuğrul, Emine Merve et al. “Synthesis, Characterization and in Vitro Cytotoxic Activity of platinum(II) Oxalato Complexes Involving 2-Substitutedimidazole or 2-Substitutedbenzimidazole Derivatives As Carrier Ligands”. İstanbul Journal of Pharmacy 53/3 (December 2023), 308-313. https://doi.org/10.26650/IstanbulJPharm.2023.1266118.
JAMA Ertuğrul EM, Özçelik AB, Çerçi NA, Açık L, Utku S. Synthesis, characterization and in vitro cytotoxic activity of platinum(II) oxalato complexes involving 2-substitutedimidazole or 2-substitutedbenzimidazole derivatives as carrier ligands. iujp. 2023;53:308–313.
MLA Ertuğrul, Emine Merve et al. “Synthesis, Characterization and in Vitro Cytotoxic Activity of platinum(II) Oxalato Complexes Involving 2-Substitutedimidazole or 2-Substitutedbenzimidazole Derivatives As Carrier Ligands”. İstanbul Journal of Pharmacy, vol. 53, no. 3, 2023, pp. 308-13, doi:10.26650/IstanbulJPharm.2023.1266118.
Vancouver Ertuğrul EM, Özçelik AB, Çerçi NA, Açık L, Utku S. Synthesis, characterization and in vitro cytotoxic activity of platinum(II) oxalato complexes involving 2-substitutedimidazole or 2-substitutedbenzimidazole derivatives as carrier ligands. iujp. 2023;53(3):308-13.