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In Vitro Cytotoxic Evaluation of a Silver(I) Complex Including Non-Steroidal Anti-Inflammatory Drug Niflumic Acid and 3-Picoline on Human-Derived Cancer Cell Lines

Year 2022, , 736 - 748, 30.12.2022

Sema Çağlar , Ahmet Altay , Bülent Çağlar , Esma Kübra Kağan Yeniçeri , Betül Harurluoğlu

https://doi.org/10.18185/erzifbed.1130634

Abstract

Burada, steroidal olmayan anti-enflamatuar ilaç niflumik asit ve 3-pikolin içeren yeni bir gümüş(I) kompleksi sentezlendi ve FT-IR, 1H NMR, elemental ve termik analiz teknikleri ile karakterize edildi. Bu teknikler, sentezlenen kompleksin formülünün [Ag(nif)(3-pic)] olduğunu gösterdi. Kompleks, ligand (niflumik asit) ve gümüş iyonlarının tek başına sitotoksik yeteneği, insan meme adenokarsinomu (MDA-MB-453), akciğer adenokarsinomu (A-549), kolorektal adenokarsinom (HT-29) ve fare fibroblast hücre hatlarına (3T3-L1) karşı test edildi. XTT sonuçları, AgNO3 ve niflumik asidin tek başına kanser ve sağlıklı hücre hatları üzerinde orta düzeyde sitotoksisite sergilemesine rağmen, kompleksin kanser hücreleri üzerinde doza bağlı bir şekilde güçlü sitotoksik aktivite gösterdiğini gösterdi. Kompleksin en güçlü sitotoksisitesi ve en yüksek seçiciliği HT-29 hücrelerinde belirlendi. Bu bulgular, gelişmiş antikanser çalışmalarında yeni gümüş(I) kompleksinin değerlendirilmesi için temel çıktılar sağlar.

Keywords

Silver(I) complex Niflumic acid Cytotoxicity Cell culture

Supporting Institution

Erzincan Binali Yıldırım University Scientific Research Projects Coordination Commission (EU-BAP)

Project Number

FBA-2020-683

Thanks

This work was financially supported by grants from Erzincan Binali Yıldırım University Scientific Research Projects Coordination Commission (EU-BAP) (Project No: FBA-2020-683).

References

  • [1] Petersen, PE.,(2009) Oral cancer prevention and control - The approach of the World Health Organization. Oral Oncol, 45(4–5): 454–60.
  • [2] Rosenberg B. (1980) Cisplatin: Its History and Possible Mechanisms of Action, Current Status and New Developments. Academic Press, 1980.
  • [3] Benedetti BT, Peterson EJ, Kabolizadeh P, Martínez A, Kipping R, Farrell NP.(2011) Effects of noncovalent platinum drug-protein interactions on drug efficacy: Use of fluorescent conjugates as probes for drug metabolism. Mol. Pharm, 8(3): 940–48.
  • [4] Karlenius TC, Tonissen KF. (2010) Thioredoxin and cancer: A role for thioredoxin in all states of tumor oxygenation. Cancers, 2:209–232.
  • [5] Bindoli A, Pia M, Scutari G, Gabbiani C, Casini A, Messori L.(2009) Thioredoxin reductase : A target for gold compounds acting as potential anticancer drugs. Coord. Chem. Rev., 253: 1692–707.
  • [6] Gupte A, Mumper RJ. (2009) Elevated copper and oxidative stress in cancer cells as a target for cancer treatment. Cancer Treat. Rev, 35(1): 32–46.
  • [7] Monneret, C. (2011) Platinum anticancer drugs. From serendipity to rational design. Ann. Pharm. Fr., 69(6): 286–295.
  • [8] Johnstone TC, Suntharalingam K, Lippard SJ.(2016) The Next Generation of Platinum Drugs : Targeted Pt ( II ) Agents , Nanoparticle Delivery , and Pt ( IV ) Prodrugs. Chem. Rev, 116:3436–3486.
  • [9] Mi Q, Ma Y, Gao X, Liu R, Liu P, Mi Y, Fu X, Gao Q.(2016) 2-Deoxyglucose conjugated platinum (II) complexes for targeted therapy: design, synthesis, and antitumor activity. J. Biomol. Struct. Dyn, 34(11): 2339–50.
  • [10] Hindi KM, Panzner MJ, Tessier CA, Cannon CL, Youngs WJ.(2009) The Medicinal Applications of Imidazolium Carbene−Metal Complexes. Chem. Rev, 109(8): 3859–3884.
  • [11] Gasser G, Ott I, Metzler-Nolte N.(2011) Organometallic anticancer compounds. J. Med. Chem, 54:3–25.
  • [12] Pedro M, Mara M, Lidia C.(2014) Organometallic Compounds in Cancer Therapy: Past Lessons and Future Directions. Bentham Sci. Publ, 14:1199–1214.
  • [13] Kunkely H, Vogler A.(2011) Absorption and luminescence spectra of cochineal. Inorg. Chem. Commun, 14:1153–1155.
  • [14] Li S, Zhang S, Jin X, Tan X, Lou J, Zhang X, Zhao Y.(2014) Singly protonated dehydronorcantharidin silver coordination polymer induces apoptosis of lung cancer cells via reactive oxygen species-mediated mitochondrial pathway. Eur. J. Med. Chem, 86: 1–11.
  • [15] Mahendiran D, Kumar RS, Rahiman AK.(2017) Heteroleptic silver(I) complexes with 2,2′:6′,2″-terpyridines and naproxen: DNA interaction, EGFR/VEGFR2 kinase, growth inhibition and cell cycle arrest studies. Mater. Sci. Eng. C, 76:601–615.
  • [16] Johnsen, JI, Lindskog M, Ponthan F, Pettersen I.(2005) NSAIDs in neuroblastoma therapy. Cancer Lett, 228(1–2): 195–201.
  • [17] Banti CN, Giannoulis AD, Kourkoumelis N, Owczarzak AM, Kubickic M, Hadjikakou SK.(2014) Novel metallo-therapeutics of the NSAID naproxen. Interaction with intracellular components that leads the cells to apoptosis. Dalt. Trans, 18: 6848–63.
  • [18] Ho Woo D, Han IS, Jung G.(2004) Mefenamic acid-induced apoptosis in human liver cancer cell-lines through caspase-3 pathway. Life Sci, 75:2439–2449.
  • [19] Kyros L, Banti CN, Kourkoumelis N, Kubicki M, Sainis I, Hadjikakou SK.(2014) Synthesis, characterization, and binding properties towards CT-DNA and lipoxygenase of mixed-ligand silver (I) complexes with 2-mercaptothiazole and its derivatives and triphenylphosphine. J. Biol. Inorg. Chem, 6: 449–464.
  • [20] Núñez C, Fernández-Lodeiro A, Fernández-Lodeiro J, Carballo J, Capelo JL, Lodeiro C.(2014) Synthesis, spectroscopic studies and in vitro antibacterial activity of Ibuprofen and its derived metal complexes. Inorg. Chem. Commun, 45: 61–65.
  • [21] Pereira IM, De Moraes Profirio D, De Paiva REF, Lancellotti M, Barboza Formiga AL, Corbi PP.(2013) A silver complex with ibuprofen: Synthesis, solid state characterization, DFT calculations and antibacterial assays. J. Mol. Struct, 1049: 1–6.
  • [22] Altay A, Bozoğlu F.(2017) Salvia fruticosa Modulates mRNA Expressions and Activity Levels of Xenobiotic Metabolizing CYP1A2, CYP2E1, NQO1, GPx, and GST Enzymes in Human Colorectal Adenocarcinoma HT-29 Cells. Nutr. Cancer,0:1–12.
  • [23] Harurluoglu B, Altay A, Caglar S, Kubra E, Yeniceri K, Caglar B, Sahin ZS.(2021) Binuclear silver (I) complexes with the non-steroidal anti-inflammatory drug tolfenamic acid: Synthesis, characterization, cytotoxic activity and evaluation of cellular mechanism of action. Polyhedron,202:115189.
  • [24] Liao WC, Chou CT, Liang WZ, Hao LJ, Kuo CC, Lin KL, Wang JL, Jan, CR.(2018) Exploration of niflumic acid’s action on Ca2+ movement and cell viability in human osteosarcoma cells. Chin. J. Physiol, 61(6): 341–48.
  • [25] Ramar M, Manikandan B, Marimuthu PN, Raman T, Mahalingam A, Subramanian P, Karthick S, Munusamy A.(2015) Synthesis of silver nanoparticles using Solanum trilobatum fruits extract and its antibacterial, cytotoxic activity against human breast cancer cell line MCF 7. Spectrochim. Acta - Part A Mol. Biomol. Spectrosc.,140: 223–228.
  • [26] Miura N, Shinohara Y.(2009) Cytotoxic effect and apoptosis induction by silver nanoparticles in HeLa cells. Biochem. Biophys. Res. Commun ,390:733–737.
  • [27] Smolko L, Smolková R, Samoľová E, Morgan I, Saoud M, Kaluđerović GN.(2020) Two isostructural Co (II) flufenamato and niflumato complexes with bathocuproine : Analogues with a different cytotoxic activity. J. Inorg. Biochem, 111160.
  • [28] Smolko L, Špaková I, Klepcová Z, Dubayová K, Samoľová E, Rabajdová M, Mareková M.(2021) Zinc(II) niflumato complex with neocuproine: Synthesis, crystal structure, characterization and cytotoxic effects on human endometrial cell lines. J. Mol. Struct, 1237.
  • [29] Altay A, Caglar S, Caglar B.(2022) Silver(I) complexes containing diclofenac and niflumic acid induce apoptosis in human-derived cancer cell lines. Arch. Physiol. Biochem,128:69-79.
  • [30] Altay A, Caglar S, Caglar B, Sahin ZS.(2019) Novel silver(I) complexes bearing mefenamic acid and pyridine derivatives: Synthesis, chemical characterization and in vitro anticancer evaluation, Inorganica Chim. Acta, 493: 61–71.
  • [31] Caglar S, Altay A. Harurluoğlu, B. and Caglar, B.(2021) Trinuclear silver(I) complex of non-steroidal anti-inflammatory drug naproxen: Synthesis, characterization, and in vitro cytotoxicity, Maced. J. Chem. Chem. Eng, 40(2): 171-80.
  • [32] Caglar S, Altay A.(2021) In Vitro Anticancer Activity of Novel Co (II) and Ni (II) Complexes of Non-steroidal Anti-in fl ammatory Drug Niflumic Acid Against Human Breast Adenocarcinoma MCF-7 Cells, Cell Biochem. Biophys, 79(4): 729-46.
  • [33] Adolfo R, Marta C, Pedro L, Otaciro N, Daniel D, Joaquín L, Ignácio L, Lucas B, Luis L, Diógenes I.(2021) Synergy of DNA intercalation and catalytic activity of a copper complex towards improved polymerase inhibition and cancer cell cytotoxicity. Dalt. Trans, 34.
  • [34] Umar N, Ndumiso M, Mahmoud ES.(2017) Metal complexes in cancer therapy – an update from drug design perspective. Drug Des Devel Ther,11: 599–616.

Year 2022, , 736 - 748, 30.12.2022

Sema Çağlar , Ahmet Altay , Bülent Çağlar , Esma Kübra Kağan Yeniçeri , Betül Harurluoğlu

https://doi.org/10.18185/erzifbed.1130634

Abstract

Project Number

FBA-2020-683

References

  • [1] Petersen, PE.,(2009) Oral cancer prevention and control - The approach of the World Health Organization. Oral Oncol, 45(4–5): 454–60.
  • [2] Rosenberg B. (1980) Cisplatin: Its History and Possible Mechanisms of Action, Current Status and New Developments. Academic Press, 1980.
  • [3] Benedetti BT, Peterson EJ, Kabolizadeh P, Martínez A, Kipping R, Farrell NP.(2011) Effects of noncovalent platinum drug-protein interactions on drug efficacy: Use of fluorescent conjugates as probes for drug metabolism. Mol. Pharm, 8(3): 940–48.
  • [4] Karlenius TC, Tonissen KF. (2010) Thioredoxin and cancer: A role for thioredoxin in all states of tumor oxygenation. Cancers, 2:209–232.
  • [5] Bindoli A, Pia M, Scutari G, Gabbiani C, Casini A, Messori L.(2009) Thioredoxin reductase : A target for gold compounds acting as potential anticancer drugs. Coord. Chem. Rev., 253: 1692–707.
  • [6] Gupte A, Mumper RJ. (2009) Elevated copper and oxidative stress in cancer cells as a target for cancer treatment. Cancer Treat. Rev, 35(1): 32–46.
  • [7] Monneret, C. (2011) Platinum anticancer drugs. From serendipity to rational design. Ann. Pharm. Fr., 69(6): 286–295.
  • [8] Johnstone TC, Suntharalingam K, Lippard SJ.(2016) The Next Generation of Platinum Drugs : Targeted Pt ( II ) Agents , Nanoparticle Delivery , and Pt ( IV ) Prodrugs. Chem. Rev, 116:3436–3486.
  • [9] Mi Q, Ma Y, Gao X, Liu R, Liu P, Mi Y, Fu X, Gao Q.(2016) 2-Deoxyglucose conjugated platinum (II) complexes for targeted therapy: design, synthesis, and antitumor activity. J. Biomol. Struct. Dyn, 34(11): 2339–50.
  • [10] Hindi KM, Panzner MJ, Tessier CA, Cannon CL, Youngs WJ.(2009) The Medicinal Applications of Imidazolium Carbene−Metal Complexes. Chem. Rev, 109(8): 3859–3884.
  • [11] Gasser G, Ott I, Metzler-Nolte N.(2011) Organometallic anticancer compounds. J. Med. Chem, 54:3–25.
  • [12] Pedro M, Mara M, Lidia C.(2014) Organometallic Compounds in Cancer Therapy: Past Lessons and Future Directions. Bentham Sci. Publ, 14:1199–1214.
  • [13] Kunkely H, Vogler A.(2011) Absorption and luminescence spectra of cochineal. Inorg. Chem. Commun, 14:1153–1155.
  • [14] Li S, Zhang S, Jin X, Tan X, Lou J, Zhang X, Zhao Y.(2014) Singly protonated dehydronorcantharidin silver coordination polymer induces apoptosis of lung cancer cells via reactive oxygen species-mediated mitochondrial pathway. Eur. J. Med. Chem, 86: 1–11.
  • [15] Mahendiran D, Kumar RS, Rahiman AK.(2017) Heteroleptic silver(I) complexes with 2,2′:6′,2″-terpyridines and naproxen: DNA interaction, EGFR/VEGFR2 kinase, growth inhibition and cell cycle arrest studies. Mater. Sci. Eng. C, 76:601–615.
  • [16] Johnsen, JI, Lindskog M, Ponthan F, Pettersen I.(2005) NSAIDs in neuroblastoma therapy. Cancer Lett, 228(1–2): 195–201.
  • [17] Banti CN, Giannoulis AD, Kourkoumelis N, Owczarzak AM, Kubickic M, Hadjikakou SK.(2014) Novel metallo-therapeutics of the NSAID naproxen. Interaction with intracellular components that leads the cells to apoptosis. Dalt. Trans, 18: 6848–63.
  • [18] Ho Woo D, Han IS, Jung G.(2004) Mefenamic acid-induced apoptosis in human liver cancer cell-lines through caspase-3 pathway. Life Sci, 75:2439–2449.
  • [19] Kyros L, Banti CN, Kourkoumelis N, Kubicki M, Sainis I, Hadjikakou SK.(2014) Synthesis, characterization, and binding properties towards CT-DNA and lipoxygenase of mixed-ligand silver (I) complexes with 2-mercaptothiazole and its derivatives and triphenylphosphine. J. Biol. Inorg. Chem, 6: 449–464.
  • [20] Núñez C, Fernández-Lodeiro A, Fernández-Lodeiro J, Carballo J, Capelo JL, Lodeiro C.(2014) Synthesis, spectroscopic studies and in vitro antibacterial activity of Ibuprofen and its derived metal complexes. Inorg. Chem. Commun, 45: 61–65.
  • [21] Pereira IM, De Moraes Profirio D, De Paiva REF, Lancellotti M, Barboza Formiga AL, Corbi PP.(2013) A silver complex with ibuprofen: Synthesis, solid state characterization, DFT calculations and antibacterial assays. J. Mol. Struct, 1049: 1–6.
  • [22] Altay A, Bozoğlu F.(2017) Salvia fruticosa Modulates mRNA Expressions and Activity Levels of Xenobiotic Metabolizing CYP1A2, CYP2E1, NQO1, GPx, and GST Enzymes in Human Colorectal Adenocarcinoma HT-29 Cells. Nutr. Cancer,0:1–12.
  • [23] Harurluoglu B, Altay A, Caglar S, Kubra E, Yeniceri K, Caglar B, Sahin ZS.(2021) Binuclear silver (I) complexes with the non-steroidal anti-inflammatory drug tolfenamic acid: Synthesis, characterization, cytotoxic activity and evaluation of cellular mechanism of action. Polyhedron,202:115189.
  • [24] Liao WC, Chou CT, Liang WZ, Hao LJ, Kuo CC, Lin KL, Wang JL, Jan, CR.(2018) Exploration of niflumic acid’s action on Ca2+ movement and cell viability in human osteosarcoma cells. Chin. J. Physiol, 61(6): 341–48.
  • [25] Ramar M, Manikandan B, Marimuthu PN, Raman T, Mahalingam A, Subramanian P, Karthick S, Munusamy A.(2015) Synthesis of silver nanoparticles using Solanum trilobatum fruits extract and its antibacterial, cytotoxic activity against human breast cancer cell line MCF 7. Spectrochim. Acta - Part A Mol. Biomol. Spectrosc.,140: 223–228.
  • [26] Miura N, Shinohara Y.(2009) Cytotoxic effect and apoptosis induction by silver nanoparticles in HeLa cells. Biochem. Biophys. Res. Commun ,390:733–737.
  • [27] Smolko L, Smolková R, Samoľová E, Morgan I, Saoud M, Kaluđerović GN.(2020) Two isostructural Co (II) flufenamato and niflumato complexes with bathocuproine : Analogues with a different cytotoxic activity. J. Inorg. Biochem, 111160.
  • [28] Smolko L, Špaková I, Klepcová Z, Dubayová K, Samoľová E, Rabajdová M, Mareková M.(2021) Zinc(II) niflumato complex with neocuproine: Synthesis, crystal structure, characterization and cytotoxic effects on human endometrial cell lines. J. Mol. Struct, 1237.
  • [29] Altay A, Caglar S, Caglar B.(2022) Silver(I) complexes containing diclofenac and niflumic acid induce apoptosis in human-derived cancer cell lines. Arch. Physiol. Biochem,128:69-79.
  • [30] Altay A, Caglar S, Caglar B, Sahin ZS.(2019) Novel silver(I) complexes bearing mefenamic acid and pyridine derivatives: Synthesis, chemical characterization and in vitro anticancer evaluation, Inorganica Chim. Acta, 493: 61–71.
  • [31] Caglar S, Altay A. Harurluoğlu, B. and Caglar, B.(2021) Trinuclear silver(I) complex of non-steroidal anti-inflammatory drug naproxen: Synthesis, characterization, and in vitro cytotoxicity, Maced. J. Chem. Chem. Eng, 40(2): 171-80.
  • [32] Caglar S, Altay A.(2021) In Vitro Anticancer Activity of Novel Co (II) and Ni (II) Complexes of Non-steroidal Anti-in fl ammatory Drug Niflumic Acid Against Human Breast Adenocarcinoma MCF-7 Cells, Cell Biochem. Biophys, 79(4): 729-46.
  • [33] Adolfo R, Marta C, Pedro L, Otaciro N, Daniel D, Joaquín L, Ignácio L, Lucas B, Luis L, Diógenes I.(2021) Synergy of DNA intercalation and catalytic activity of a copper complex towards improved polymerase inhibition and cancer cell cytotoxicity. Dalt. Trans, 34.
  • [34] Umar N, Ndumiso M, Mahmoud ES.(2017) Metal complexes in cancer therapy – an update from drug design perspective. Drug Des Devel Ther,11: 599–616.
There are 34 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Makaleler
Authors

Sema Çağlar 0000-0002-7424-2315

Ahmet Altay 0000-0001-8120-8900

Bülent Çağlar 0000-0002-6087-3685

Esma Kübra Kağan Yeniçeri 0000-0002-6860-9758

Betül Harurluoğlu 0000-0003-2521-9677

Project Number FBA-2020-683
Publication Date December 30, 2022
Published in Issue Year 2022

Cite

APA Çağlar, S., Altay, A., Çağlar, B., Kağan Yeniçeri, E. K., et al. (2022). In Vitro Cytotoxic Evaluation of a Silver(I) Complex Including Non-Steroidal Anti-Inflammatory Drug Niflumic Acid and 3-Picoline on Human-Derived Cancer Cell Lines. Erzincan University Journal of Science and Technology, 15(3), 736-748. https://doi.org/10.18185/erzifbed.1130634