Synthesis and characterization of copper(II) octaazamacrocyclic complexes with glycine derivatives. In vitro antiproliferative and antimicrobial evaluation of the Cu(II) and Co(II) analogous

Main Article Content

Branka Dražić
Mirjana Antonijevič Nikolić
Željko Žižak
Slađana Tanasković

Abstract

T

Two new complexes with the general formula [Cu2(L)tpmc](ClO4)3·nH2O (tpmc = N,N¢,N¢¢,N¢¢¢-tetrakis(2-pyridylmethyl)-1,4,8,11-tetraazacyclotetradecane, L = N-methylglycine, n = 3; L = N,N-dimethylglycine, n = 2) were isolated and their composition, some physical and chemical properties and geometries were proposed based on elemental analysis (C, H, N), conductometric and magnetic measurements and spectro­scopic data (UV–Vis, FTIR). It is evident that the complexes are binuclear and an exo coordination mode of the macrocyclic ligand in the boat conformation was proposed. The co-ligands are coordinated as a bridge using both oxygen atoms of the OCO- group. The cytotoxic activity of Cu(II) complexes as well as their Co(II) analogs, the starting ligands and the free salts were tested against human cervix adenocarcinoma cell line (HeLa), human chronic myelo­genous leukemia cells (K562), human breast cancer cell line (MDA-MB-453), and a non-cancerous cell line, human embryonic lung fibroblast (MRC-5). The IC50 values for the Cu(II) complexes were from 21.6±0.04 to 66.1±0.8, and for the Co(II) analogs were within the range from 8.8±0.74 to 15.40±1.52. All four complexes were tested for their antimicrobial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and the yeast Candida albicans.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

Article Details

How to Cite
[1]
B. Dražić, M. Antonijevič Nikolić, Željko Žižak, and S. Tanasković, “Synthesis and characterization of copper(II) octaazamacrocyclic complexes with glycine derivatives. In vitro antiproliferative and antimicrobial evaluation of the Cu(II) and Co(II) analogous”, J. Serb. Chem. Soc., vol. 85, no. 5, pp. 637–649, May 2020.
Section
Inorganic Chemistry

References

G. B. Bagihalli, P. G. Avaji, S. A. Patil, P. S. Badami, Eur. J. Med. Chem. 43 (2008) 2639 (https://dx.doi.org/10.1016/j.ejmech.2008.02.013)

Y. Wan, S. He, W. Li, Z. Tang, Anti Cancer Agents Med. Chem. 18 (2018) 1228 (https://dx.doi.org/10.2174/1871520618666180510113822)

Z. H. Chohan, M. Arif, M. A. Akhtar, C. T. Supuran, Bioinorg. Chem. Appl. 2006, ID 83131, 1 (https://dx.doi.org/10.1155/BCA/2006/83131)

H. Fałtynowicz, M. Daszkiewicz, R. Wysokinski, A. Adach, M. Cieslak-Golonka, Struct. Chem. 26 (2015) 1555 (https://dx.doi.org/10.1007/s11224-015-0631-7)

P. A. Vigato, S. Tamburini, Coord. Chem. Rev. 248 (2004) 1717 (https://dx.doi.org/10.1016/j.cct.2003.09.003)

W. Sibert, A. H. Cory, J. G. Cory, Chem. Commun. 2 (2002) 154 (https://dx.doi.org/10.1039/b107899m)

S. J. Paisey, P. J. Sadler, Chem. Commun. 3 (2004) 306 (https://dx.doi.org/10.1039/B312752B)

Qi.-Y. Yang, Q. Q. Cao, Q. P. Qin, C. X. Deng, H. Liang, Z. F. Chen, Int. J. Mol. Sci. 19 (2018) 1874 (https://dx.doi.org/10.3390/ijms19071874)

Z. Lakovidou, A. Papageorgiou, M. A. Demertzis, E. Mioglou, D. Mourelatos, A. Kotsis, P. N. Yadav, D. Kovala-Demertzi, Anti-Cancer Drugs 12 (2001) 65 (https://www.ncbi.nlm.nih.gov/pubmed/11272288)

A. Fetoh, K. A. Asla, A. A. El-Sherif, H. El-Didamony, G. M. Abu El-Reash, J. Mol. Struct. 1178 (2019) 524 (https://doi.org/10.1016/j.molstruc.2018.10.066)

P. M. Reddy, R. Rohini, E. Ravi Krishna, A. Hu, V. Ravinder, Int. J. Mol. Sci. 13 (2012) 4982 (https://dx.doi.org/10.3390/ijms13044982)

R. S. Prabhat, R. Singh, S. Pawar, A. Chauhan, J. Am. Sci. 6 (2010) 559 (http://ijsetr.org/wp-content/uploads/2016/10/IJSETR-VOL-5-ISSUE-10-2964-2967.pdf)

C. S. Dilip, V. Sivakumar, J. J. Prince, Indian J. Chem. Tech. 19 (2012) 351 (http://nopr.niscair.res.in/handle/123456789/14682)

M. Antonijević-Nikolić, J. Antić-Stanković, S. B. Tanasković, M. J. Korabik, G. Gojgić-

-Cvijović, G. Vučković, J. Mol. Struct. 1054–1055 (2013) 297 (https://doi.org/10.1016/j.molstruc.2013.10.006)

G. Vučković, S. B. Tanasković, M. Antonijević-Nikolić, V. Živković-Radovanović, G. Gojgić-Cvijović, J. Serb. Chem. Soc. 74 (2009) 629 (https://dx.doi.org/10.2298/JSC0906629V)

S. Chandrasekhar, W. L. Waltz, L. Prasad, J. W. Quail, Can. J. Chem. 75 (1997) 1363 (https://doi.org/10.1139/v97-164)

E. Asato, H. Toftlund, S. Kida, M. Mikuriya, K. S. Murray, Inorg. Chim. Acta 165 (1989) 207 (http://dx.doi.org/10.1016/S0020-1693(00)83241-7)

E. Konig, Magnetic Properties of Coordination and Organometallic Transition Metal Compounds, Springer-Verlag, Berlin, 1966, p. 345

T. Mosmann, J. Immunol. Methods 65 (1983) 55 (http://dx.doi.org/10.1016/0022-1759(83)90303-4)

M. Ohno, T. Abe, J. Immunol. Methods 145 (1991) 199 (https://www.ncbi.nlm.nih.gov/pubmed/1765652)

W. J. Gear, Coord. Chem. Rev. 7 (1971) 81

(https://dx.doi.org/10.1016/S0010-8545(00)80009-0)

F. A. Cotton, G. Wilkinson, C. A. Murillo, M. Bochmann. Advanced Inorganic Chemistry, 6th ed., Wiley, New York, 1999, p. 854

G. Vučković, M. Antonijević, D. Poleti, J. Serb. Chem. Soc. 67 (2002) 677

Z. M. Miodragović, G. Vučković, V. M. Leovac, J. Serb. Chem. Soc. 66 (2001) 597 (https://doi.org/10.2298/JSC0109597M)

G. Vučković, M. Antonijević-Nikolić, S. B. Tanasković, V. Živković-Radovanović, J. Serb. Chem. Soc. 76 (2011) 719 (https://doi.org/10.2298/JSC101201062V)

A. B. P. Lever, Inorganic Electronic Spectroscopy, 2nd ed., Elsevier, Amsterdam, 1984, p. 554

K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B, 5th ed., Wiley, New York, 1997, p. 23, 59, 83, 271 (ISBN:978-0-471-74493-1)

G. Deacon, R. J. Philips, Coord. Chem. Rev. 33 (1980) 227 (https://doi.org/10.1016/S0010-8545(00)80455-5)

A. Stănilă, C. Braicu, S. Stănilă, R. M. Pop, Not. Bot. Horti. Agrobot. Cluj Napoca 39 (2011) 124 (https://doi.org/10.15835/nbha3926847)

K. Carroll, J. Butel, S. Morse, Jawetz, Melnick & Adelbergs Medical Microbiology, 27th ed., McGraw-Hill Education, New York, 2016

Y. Arafat, S. Ali, S. Shahzadi, M. Shahid, Bioinorg. Chem. Applic. (2013) Article ID 351262 (http://dx.doi.org/10.1155/2013/351262)

J. B. Dalmarco, E. M. Dalmarco, J. Koelzer, M. G. Pizzolatti, T. S. Fröde, Int. J. Green Pharm. 4 (2010) 108 (http://dx.doi.org/10.22377/ijgp.v4i2.130).