SYNTHESIS AND CHARACTERISTICS OF FOUR NEW COPPER(II) CARBOXYLATE COMPLEXES WITH ADAMANTANE FRAGMENT
Аннотация и ключевые слова
Аннотация (русский):
The paper considers the results of synthesis, elemental analysis, and spectroscopic methods (IR, UV-vis) of four new copper(II) complexes with anions of 1-adamantanecarboxylic acid, 4-(1-adamantyl)benzoic acid and their L-valine derivatives as ligands. Based on the obtained spectral data, the authors assumed the biyaderic structure of these complexes with bidentate coordination of carboxylate ligands of the type [Cu2+2(RCOO-)4(H2O)2], with RCOO-as carboxylate ligands. The synthesised compounds are of interest as low toxic potential therapeutic agents with anti-inflammatory and anti-cancer activity.

Ключевые слова:
copper(II) carboxylate complexes, 1-adamantane carboxylic acid, 4-(1-adamantyl)benzoic acid, biuclear complexes
Текст
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Список литературы

1. Medici, S., Peana, M., Nurchi, V.M., Lachowicz, J.I., Crisponi, G. & Zoroddu, M.A. (2015) Noble metals in medicine: Latest advances, Coord. Chem. Rev., 284, pp. 329-350. DOI:https://doi.org/10.1016/j.ccr.2014.08.002.

2. Ruiz-Azuara, L. & Bravo-Gomez, M.E. (2010) Copper Compounds in Cancer Chemotherapy, Curr. Med. Chem., 17, pp. 3606-3615. DOI:https://doi.org/10.2174/092986710793213751.

3. Fernandes, P., Sousa, I., Cunha-Silva, L., Ferreira, M., de Castro, B., Pereira, E.F., Feio, M.J. & Gameiro, P. (2014) Synthesis, characterization and antibacterial studies of a copper(II) lomefloxacin ternary complex, J. Inorg. Biochem., 131, pp. 21-29. DOI:https://doi.org/10.1016/j.jinorgbio.2013.10.013.

4. Martins, D.A., Gouvea, L.R., da Gama Jean Batista, D., da Silva, P.B., Louro, S.R.W., de Nazaré, C., Soeiro, M. & Teixeira, L.R. (2012) Copper(II)–fluoroquinolone complexes with anti-Trypanosoma cruzi activity and DNA binding ability, Biometals, 25, pp. 951-960. DOI:https://doi.org/10.1007/s10534-012-9565-3.

5. Perontsis, S., Hatzidimitriou, A.G., Begou, O.-A., Papadopoulos, A.N. & Psomas, G. (2016) Characterization and biological properties of copper(II)-ketoprofen complexes, J. Inorg. Biochem., 162, pp. 22-30. DOI:https://doi.org/10.1016/j.jinorgbio.2016.06.001.

6. Psomas, G. (2020) Copper(II) and zinc(II) coordination compounds of non-steroidal anti-inflammatory drugs: Structural features and antioxidant activity, Coord. Chem. Rev., 412, 213259. DOI:https://doi.org/10.1016/j.ccr.2020.213259.

7. Jeong, Y.W., Kim, K.S., Oh, J.Y., Park, J.C., Bang, J.H., Choi, S.W. & Lee, J.C. (2003) Growth Inhibition and Apoptosis Induction of Gastric Cancer Cells by Copper (II) Glycinate Complex, J. Microbiol. Biotechnol., 13, pp. 394-399 [online]. Available at: https://www.jmb.or.kr/journal/download_pdf.php?spage=394&volume=13&number=3 (accessed 12.01.2024)

8. Iglesias, S., Alvarez, N., Torre, M.H., Kremer, E., Ellena, J., Ribeiro, R.R., Barroso, R.P., Costa-Filho, A.J., Kramer, G.M. & Facchin, G. (2014) Synthesis, structural characterization and cytotoxic activity of ternary Copper(II)-dipeptide-phenanthroline complexes. A step towards the development of new copper compounds for the treatment of cancer, J. Inorg. Biochem., 139, pp. 117-123. DOI:https://doi.org/10.1016/j.jinorgbio.2014.06.007.

9. Fernández, C.Y., Alvarez, N., Rocha, A., Ellena, J., Costa-Filho, A.J., Batista, A.A. & Facchin, G. (2023) New Copper(II)-L-Dipeptide-Bathophenanthroline Complexes as Potential Anticancer Agents — Synthesis, Characterization and Cytotoxicity Studies – And Comparative DNA-Binding Study of Related Phen Complexes, Molecules, 28, 896. DOI:https://doi.org/10.3390/molecules28020896.

10. Banti, C.N. & Hadjikakou, S.K. (2016) Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) in Metal Complexes and Their Effect at the Cellular Level, Eur. J. Inorg. Chem., 2016, pp. 3048-3071. DOI:https://doi.org/10.1002/ejic.201501480.

11. Krstić, N.S., Nikolić, R.S., Stanković, M.N., Nikolić, N.G. & Đorđević, D.M. (2015) Coordination Compounds of M(II) Biometal Ions with Acid-Type Anti-inflammatory Drugs as Ligands – A Review, Trop. J. Pharm. Res., 14, pp. 337-349. DOI:https://doi.org/10.4314/tjpr.v14i2.21.

12. Malis, G., Geromichalou, E., Geromichalos, G.D., Hatzidimitriou, A.G. & Psomas, G. (2021) Copper(II) complexes with non-steroidal anti-inflammatory drugs: Structural characterization, in vitro and in silico biological profile, J. Inorg. Biochem., 224, 111563. DOI:https://doi.org/10.1016/j.jinorgbio.2021.111563.

13. Krasnikov, S.V., Obuchova, T.A., Yasinskii O.A. & Balakin, K.V. (2004) Synthesis of amino acid derivatives of 4-(l-adamantyl)benzoic acid obtained by transition metal ion catalyzed oxidation of 4-(l-adamantyl)toluene, Tetrahedron Lett., 4, pp. 711-714. DOI:https://doi.org/10.1016/j.tetlet.2003.11.057.

14. Spiridonova, A.V., Uvarovskaya, P.A., Krasnikova, N.V., Krasnikov, S.V. & Rozaeva, E.E. (2021) Short N-acyldipeptides with adamantylbenzoyl fragment with potential antiviral activity, From Chemistry towards Technology Step-By-Step, 2(2), pp. 60-68. DOI:https://doi.org/10.52957/27821900_2021_02_60 [online]. Available at: http://chemintech.ru/index.php/tor/issue/view/2021-2-2 (in Russian) (accessed 24.12.2023)

15. Wanka, L., Iqbal, K. & Schreiner, P.R. (2013) The Lipophilic Bullet Hits the Targets: Medicinal Chemistry of Adamantane Derivatives, Chem. Rev., 113, pp. 3516-3604. DOI:https://doi.org/10.1021/cr100264t.

16. Corradi, A. (1992) Structures and stabilities of metal(II) (Co(II), Ni(II), Cu(II), Zn(II), Pd(II), Cd(II)) compounds of N-protected aminoacids, Coord. Chem. Rev., 45, pp. 45-98. DOI:https://doi.org/10.1016/0010-8545(92)80020-R.

17. Marcotrigiano, G.O., Menabue, L. & Pellacani, G.C. (1980) (N-acetyl-DL-valinate)copper(II) complexes: effect of amines on the amino acid coordination, Inorg. Chim. Acta., 46, pp. 107-112. DOI:https://doi.org/10.1016/S0020-1693(00)84177-8.

18. Lutsenko, I.A., Baravikov, D.E., Koshenskova, K.A., Kiskin, M.A., Nelyubina, Y.V., Primakov, P.V., Voronina, Y.K., Garaeva, V.V., Aleshin, D.A., Aliev, T.M., Danilenko, V.N., Bekker, O.B. & Eremenko, I.L. (2022) What are the prospects for using complexes of copper(II) and zinc(II) to suppress the vital activity of Mycolicibacterium smegmatis? RSC Adv., 12, pp. 5173-5183. DOI:https://doi.org/10.1039/d1ra08555g.

19. Nakamoto, K. (2009) Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B: Applications in Coordination, Organometallic, and Bioinorganic Chemistry, 6th Edition. John Wiley & Sons, Inc.

20. Kumar, S., Garg, S., Sharma, R.P., Venugopalan, P., Tenti, L., Ferretti, V., Nivelle, L., Tarpin, M. & Guillon, E. (2017) Four monomeric copper(ii) complexes of non-steroidal anti-inflammatory drug Ibuprofen and N-donor ligands: syntheses, characterization, crystal structures and cytotoxicity studies, New J. Chem., 41, pp. 8253-8262. DOI:https://doi.org/10.1039/c7nj00247e.

21. Hadjiivanov, K.I., Panayotov, D.A., Mihaylov, M.Y., Ivanova, E.Z., Chakarova, K.K., Andonova, S.M. & Drenchev, N.L. (2021) Power of Infrared and Raman Spectroscopies to Characterize Metal-Organic Frameworks and Investigate Their Interaction with Guest Molecules, Chem. Rev., 121, pp. 1286-1424. DOI:https://doi.org/10.1021/acs.chemrev.0c00487.

22. Catterick, J. & Thornton, P. (1977) Structures and physical properties of polynuclear carboxylates, Adv. Inorg. Chem. Radiochem., 20, pp. 291-362. DOI:https://doi.org/10.1016/S0065-2792(08)60041-2.

23. Dimiza, F., Fountoulaki, S., Papadopoulos, A.N., Kontogiorgis, C.A., Tangoulis, V., Raptopoulou, C.P., Psycharis, V., Terzis, A., Kessissoglou, D.P. & Psomas, G. (2011) Non-steroidal antiinflammatory drug–copper(II) complexes: Structure and biological perspectives, Dalton Trans., 40, pp. 8555-8568. DOI:https://doi.org/10.1039/c1dt10714c.

24. Shahabadi, N. & Shiri, F. (2017) Multispectroscopic Studies on the Interaction of a Copper(II) Complex of Ibuprofen Drug with Calf Thymus DNA, Nucleosides, Nucleotides & Nucleic Acids., 36, pp. 83-106. DOI:https://doi.org/10.1080/15257770.2016.1223305.

25. Deacon, G.B. & Philips, R.J. (1980) Relationships between the carbon-oxygen stretching frequencies of carboxylato complexes and the type of carboxylate coordination, Coord. Chem. Rev., 33, pp. 227-250. DOI:https://doi.org/10.1016/S0010-8545(00)80455-5.

26. Moiseev, I.K., Makarova, N.V. & Zemtsova, M.N. Reactions of adamantanes in electrophilic media, (1999) Russ. Chem. Rev., 68, pp. 1001-1020. DOI:https://doi.org/10.1070/rc1999v068n12abeh000495.

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