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Current Medicinal Chemistry

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ISSN (Print): 0929-8673
ISSN (Online): 1875-533X

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Review Article

Current Development of Metal Complexes with Diamine Ligands as Potential Anticancer Agents

Author(s): Sonja Misirlic-Dencic, Jelena Poljarevic, Andjelka M. Isakovic, Tibor Sabo, Ivanka Markovic and Vladimir Trajkovic*

Volume 27, Issue 3, 2020

Page: [380 - 410] Pages: 31

DOI: 10.2174/0929867325666181031114306

Price: $65

Open Access Journals Promotions 2
Abstract

Background: The discovery of cisplatin and the subsequent research revealed the importance of dinitrogen-containing moiety for the anticancer action of metal complexes. Moreover, certain diamine ligands alone display cytotoxicity that contributes to the overall activity of corresponding complexes.

Objective: To summarize the current knowledge on the anticancer efficacy, selectivity, and the mechanisms of action of metal complexes with various types of diamine ligands.

Methods: The contribution of aliphatic acyclic, aliphatic cyclic, and aromatic diamine ligands to the anticancer activity and selectivity/toxicity of metal complexes with different metal ions were analyzed by comparison with organic ligand alone and/or conventional platinum-based chemotherapeutics.

Results: The aliphatic acyclic diamine ligands are present mostly in complexes with platinum. Aliphatic cyclic diamines are part of Pt(II), Ru(II) and Au(III) complexes, while aromatic diamine ligands are found in Pt(II), Ru(II), Pd(II) and Ir(III) complexes. The type and oxidation state of metal ions greatly influences the cytotoxicity of metal complexes with aliphatic acyclic diamine ligands. Lipophilicity of organic ligands, dependent on alkyl-side chain length and structure, determines their cellular uptake, with edda and eddp/eddip ligands being most useful in this regard. Aliphatic cyclic diamine ligands improved the activity/toxicity ratio of oxaliplatin-type complexes. The complexes with aromatic diamine ligands remain unexplored regarding their anticancer mechanism. The investigated complexes mainly caused apoptotic or necrotic cell death.

Conclusion: Metal complexes with diamine ligands are promising candidates for efficient and more selective alternatives to conventional platinum-based chemotherapeutics. Further research is required to reveal the chemico-physical properties and molecular mechanisms underlying their biological activity.

Keywords: Metal complex, diamine ligand, anticancer, in vitro, in vivo, toxicity.

« Previous Next »
[1]
Wheate, N.J.; Walker, S.; Craig, G.E.; Oun, R. The status of platinum anticancer drugs in the clinic and in clinical trials. Dalton Trans., 2010, 39(35), 8113-8127.
[http://dx.doi.org/10.1039/c0dt00292e] [PMID: 20593091]
[2]
Eckstein, N. Platinum resistance in breast and ovarian cancer cell lines. J. Exp. Clin. Cancer Res., 2011, 30(1), 91.
[http://dx.doi.org/10.1186/1756-9966-30-91] [PMID: 21967738]
[3]
Chen, H.H.W.; Kuo, M.T. Overcoming platinum drug resistance with copper-lowering agents. Anticancer Res., 2013, 33(10), 4157-4161.
[PMID: 24122978]
[4]
Huang, R.; Wallqvist, A.; Covell, D.G. Anticancer metal compounds in NCI’s tumor-screening database: putative mode of action. Biochem. Pharmacol., 2005, 69(7), 1009-1039.
[http://dx.doi.org/10.1016/j.bcp.2005.01.001] [PMID: 15763539]
[5]
Chu, K.C.; Feldmann, R.J.; Shapiro, M.B.; Hazard, G.F. Jr.; Geran, R.I. Pattern recognitiion and structure-activity relationship studies. Computer-assisted prediction of antitumor activity in structurally diverse drugs in an experimental mouse brain tumor system. J. Med. Chem., 1975, 18(6), 539-545.
[http://dx.doi.org/10.1021/jm00240a001] [PMID: 1097689]
[6]
Estrada, E.; Uriarte, E.; Montero, A.; Teijeira, M.; Santana, L.; De Clercq, E. A novel approach for the virtual screening and rational design of anticancer compounds. J. Med. Chem., 2000, 43(10), 1975-1985.
[http://dx.doi.org/10.1021/jm991172d] [PMID: 10821710]
[7]
Misirlic Dencic, S.; Poljarevic, J.; Vilimanovich, U.; Bogdanovic, A.; Isakovic, A.J.; Kravic Stevovic, T.; Dulovic, M.; Zogovic, N.; Isakovic, A.M.; Grguric-Sipka, S.; Bumbasirevic, V.; Sabo, T.; Trajkovic, V.; Markovic, I. Cyclohexyl analogues of ethylenediamine dipropanoic acid induce caspase-independent mitochondrial apoptosis in human leukemic cells. Chem. Res. Toxicol., 2012, 25(4), 931-939.
[http://dx.doi.org/10.1021/tx3000329] [PMID: 22401584]
[8]
Savić, A.; Misirlić-Denčić, S.; Dulović, M.; Mihajlović-Lalić, L.E.; Jovanović, M.; Grgurić-Šipka, S.; Marković, I.; Sabo, T.J. Synthesis, characterization and ROS-mediated cytotoxic action of novel (S,S)-1,3-propanediamine-N,N′-di-2-(3-cyclohexyl)propanoic acid and corresponding esters. Bioorg. Chem., 2014, 54, 73-80.
[http://dx.doi.org/10.1016/j.bioorg.2014.04.006] [PMID: 24836201]
[9]
Chin, C.F.; Wong, D.Y.Q.; Jothibasu, R.; Ang, W.H. Anticancer platinum (IV) prodrugs with novel modes of activity. Curr. Top. Med. Chem., 2011, 11(21), 2602-2612.
[http://dx.doi.org/10.2174/156802611798040778] [PMID: 22039869]
[10]
Ding, S.; Pickard, A.J.; Kucera, G.L.; Bierbach, U. Design of enzymatically cleavable prodrugs of a potent platinum-containing anticancer agent. Chemistry, 2014, 20(49), 16164-16173.
[http://dx.doi.org/10.1002/chem.201404675] [PMID: 25303639]
[11]
Rosenberg, B. Platinum complex-DNA interactions and anticancer activity. Biochimie, 1978, 60(9), 859-867.
[http://dx.doi.org/10.1016/S0300-9084(78)80570-7]
[12]
Abrams, M.J.; Murrer, B.A. Metal compounds in therapy and diagnosis. Science, 1993, 261(5122), 725-730.
[http://dx.doi.org/10.1126/science.8102010] [PMID: 8102010]
[13]
Eckhardt, S. Recent progress in the development of anticancer agents. Curr. Med. Chem. Anticancer Agents, 2002, 2(3), 419-439.
[http://dx.doi.org/10.2174/1568011024606389] [PMID: 12678741]
[14]
Graziotto, M.E.; Akerfeldt, M.C.; Gunn, A.P.; Yang, K.; Somerville, M.V.; Coleman, N.V.; Roberts, B.R.; Hambley, T.W.; New, E.J. The influence of the ethane-1,2-diamine ligand on the activity of a monofunctional platinum complex. J. Inorg. Biochem., 2017, 177, 328-334.
[http://dx.doi.org/10.1016/j.jinorgbio.2017.07.029] [PMID: 28789807]
[15]
Arsenijević, M.; Milovanovic, M.; Volarevic, V.; Djeković, A.; Kanjevac, T.; Arsenijević, N.; Dukić, S.; Bugarcić, Z.D. Cytotoxicity of gold(III) complexes on A549 human lung carcinoma epithelial cell line. Med. Chem., 2012, 8(1), 2-8.
[http://dx.doi.org/10.2174/157340612799278469] [PMID: 22420544]
[16]
Zhang, J.; Ma, L.; Lu, H.; Wang, Y.; Li, S.; Wang, S.; Zhou, G. Synthesis, characterization and cytotoxicity of platinum(II)/palladium(II) complexes with 1,3-diaminopropane and 4-toluensulfonyl-L-amino acid dianion. Eur. J. Med. Chem., 2012, 58, 281-286.
[http://dx.doi.org/10.1016/j.ejmech.2012.09.052] [PMID: 23137446]
[17]
Ma, L.; Zhang, J.; Zhang, F.; Chen, C.; Li, L.; Wang, S.; Li, S. Synthesis, characterization, and cytotoxicity of complexes of palladium(II) with 1,4-diaminobutane/1,3-diaminopropane and 4-toluenesulfonyl- l -amino acid dianion. J. Coord. Chem., 2012, 65(18), 3160-3173.
[http://dx.doi.org/10.1080/00958972.2012.713102]
[18]
Kwon, Y.E. Park, J.Y.; Kim, W.K. In vitro histoculture drug response assay and in vivo blood chemistry of a novel Pt(IV) compound, K104. Anticancer Res., 2007, 27(1A), 321-326.
[PMID: 17352249]
[19]
Alvarez-Valdés, A.; Pérez, J.M.; López-Solera, I.; Lannegrand, R.; Continente, J.M.; Amo-Ochoa, P.; Camazón, M.J.; Solans, X.; Font-Bardía, M.; Navarro-Ranninger, C. Preparation and characterization of platinum(II) and (IV) complexes of 1,3-diaminepropane and 1,4-diaminebutane: circumvention of cisplatin resistance and DNA interstrand cross-link formation in CH1cisR ovarian tumor cells. J. Med. Chem., 2002, 45(9), 1835-1844.
[http://dx.doi.org/10.1021/jm010968l] [PMID: 11960495]
[20]
Silva, H.; Barra, C.V.; Rocha, F.V.; Frézard, F.; Lopes, M.T.P.; Fontes, A.P.S. Novel platinum(II) complexes of long chain aliphatic diamine ligands with oxalato as the leaving group. comparative cytotoxic activity relative to chloride precursors. J. Braz. Chem. Soc., 2010, 21(10), 1961-1967.
[http://dx.doi.org/10.1590/S0103-50532010001000023]
[21]
Tavares, T.T.; Teixeira, G.F.; Lopes, C.M.; Novato, W.T.G.; Silva, H.; Lopes, M.T.P.; De Almeida, M.V.; Grazul, R.M.; Dos Santos, H.F.; Fontes, A.P.S. Platinum(II) complexes containing long-chain hydrophobic N-alkyl-diamine ligands: synthesis, characterization, molecular modeling, and cytotoxic activity. J. Inorg. Biochem., 2012, 115, 13-19.
[http://dx.doi.org/10.1016/j.jinorgbio.2012.05.007] [PMID: 22922288]
[22]
Kaluđerović, G.N.; Schmidt, H.; Schwieger, S.; Wagner, C.; Paschke, R.; Dietrich, A.; Mueller, T.; Steinborn, D. Platinum(IV) complexes with ethylenediamine-N,N′-diacetate diester (R2edda) ligands: synthesis, characterization and in vitro antitumoral activity. Inorg. Chim. Acta, 2008, 361(5), 1395-1404.
[http://dx.doi.org/10.1016/j.ica.2007.09.010]
[23]
Kaluđerović, G.N.; Pantelić, N.; Eichhorn, T.; Bette, M.; Wagner, C.; Zmejkovski, B.B.; Schmidt, H. Platinum(II) complexes with R2edda ligands (R = Me, Et, n-Pr; Edda = Ethylenediamine-N,N′-Diacetate): synthesis and characterization. Polyhedron, 2014, 80, 53-59.
[http://dx.doi.org/10.1016/j.poly.2014.01.018]
[24]
Ng, C.H.; Kong, K.C.; Von, S.T.; Balraj, P.; Jensen, P.; Thirthagiri, E.; Hamada, H.; Chikira, M. Synthesis, characterization, DNA-binding study and anticancer properties of ternary metal(II) complexes of edda and an intercalating ligand. Dalton Trans., 2008, (4), 447-454.
[http://dx.doi.org/10.1039/B709269E] [PMID: 18185860]
[25]
Stojković, D.Lj.; Jevtić, V.V.; Radić, G.P.; Todorović, D.V.; Petrović, M.; Zarić, M.; Nikolić, I.; Baskić, D.; Trifunović, S.R. Stereospecific ligands and their complexes. XXII. Synthesis and antitumor activity of palladium(II) complexes with some esters of (S,S)-ethylenediamine-N,N′-di-(2,2′-di(4-hydroxy-benzyl))-acetic acid. J. Inorg. Biochem., 2015, 143, 111-116.
[http://dx.doi.org/10.1016/j.jinorgbio.2014.12.001] [PMID: 25528678]
[26]
Kaluderović, G.N.; Dinović, V.M.; Juranić, Z.D.; Stanojković, T.P.; Sabo, T.J. Activity of some platinum(II/IV) complexes with O,O-n-butyl-and O,O-n-pentyl-ethylenediamine-N,N′-di-3-propanoate and halogeno ligands against HeLa and K562 cell lines and human PBMC. J. Inorg. Biochem., 2005, 99(2), 488-496.
[http://dx.doi.org/10.1016/j.jinorgbio.2004.10.025] [PMID: 15621281]
[27]
Krajcinović, B.B.; Kaluderović, G.N.; Steinborn, D.; Schmidt, H.; Wagner, C.; Žižak, Z.; Juranić, Z.D.; Trifunović, S.R.; Sabo, T.J. Synthesis and in vitro antitumoral activity of novel O,O′-di-2-alkyl-(S,S)-ethylenediamine-N,N′-di-2-propanoate ligands and corresponding platinum(II/IV) complexes. J. Inorg. Biochem., 2008, 102(4), 892-900.
[http://dx.doi.org/10.1016/j.jinorgbio.2007.12.009] [PMID: 18226835]
[28]
Sabo, T.J.; Kaluderović, G.N.; Poleti, D.; Karanović, L.; Boccarelli, A.; Cannito, F.; Natile, G. Cytotoxicity of some platinum(IV) complexes with ethylenediamine-N,N′-di-3-propionato ligand. J. Inorg. Biochem., 2004, 98(8), 1378-1384.
[http://dx.doi.org/10.1016/j.jinorgbio.2004.04.023] [PMID: 15271514]
[29]
Maksimović-Ivanić, D.; Mijatović, S.; Mirkov, I.; Stošić-Grujičić, S.; Miljković, D.; Sabo, T.J.; Trajković, V.; Kaluđerović, G.N. Melanoma tumor inhibition by tetrachlorido(O,O′-dibutyl-ethylenediamine-N,N′-di-3-propionate)platinum(IV) complex: in vitro and in vivo investigations. Metallomics, 2012, 4(11), 1155-1159.
[http://dx.doi.org/10.1039/c2mt20150j] [PMID: 23014886]
[30]
Djinović, V.M.; Glodjović, V.V.; Vasić, G.P.; Trajković, V.; Klisurić, O.; Stanković, S.; Sabo, T.J.; Trifunović, S.R. Stereospecific ligands and their complexes. iv: synthesis, characterization and cytotoxicity of novel platinum(IV) complexes with ethylenediamine-N,N′-Di-S,S-2-propanoate and halogenido ligands: crystal structure of s-Cis-[Pt(S,S-Eddp)Cl2]·4H2O and Uns-Cis-[Pt(S,S-eddp)Br2. Polyhedron, 2010, 29(8), 1933-1938.
[http://dx.doi.org/10.1016/j.poly.2010.03.004]
[31]
Grguric-Sipka, S.R.; Vilaplana, R.A.; Pérez, J.M.; Fuertes, M.A.; Alonso, C.; Alvarez, Y.; Sabo, T.J.; González-Vílchez, F. Synthesis, characterization, interaction with DNA and cytotoxicity of the new potential antitumour drug cis-K[Ru(eddp)Cl(2). J. Inorg. Biochem., 2003, 97(2), 215-220.
[http://dx.doi.org/10.1016/S0162-0134(03)00281-2] [PMID: 14512200]
[32]
Kaluđerović, G.N.; Mijatović, S.A.; Zmejkovski, B.B.; Bulatović, M.Z.; Gómez-Ruiz, S.; Mojić, M.K.; Steinborn, D.; Miljković, D.M.; Schmidt, H.; Stošić-Grujičić, S.D.; Sabo, T.J.; Maksimović-Ivanić, D.D. Platinum(II/IV) complexes containing ethylenediamine-N,N′-di-2/3-propionate ester ligands induced caspase-dependent apoptosis in cisplatin-resistant colon cancer cells. Metallomics, 2012, 4(9), 979-987.
[http://dx.doi.org/10.1039/c2mt20058a] [PMID: 22820831]
[33]
Kaluđerović, G.N.; Đinović, V.M.; Juranić, Z.D.; Stanojković, T.P.; Sabo, T.J. Activity of some platinum(II/IV) complexes with edda-type ligands against human adenocarcinoma HeLa cells. J. Coord. Chem., 2006, 59(7), 815-819.
[http://dx.doi.org/10.1080/00958970500404708]
[34]
Jevtic, V.V.; Radic, G.P.; Seklic, D.S.; Zivanovic, M.N.; Markovic, S.D.; Trifunovic, S.R. Stereospecific ligands and their complexes. Part XII. Synthesis, characterization and in vitro antiproliferative activity of platinum (IV) complexes with some O,O′-Dialkyl esters of (S,S)-Ethylenediamine-N,N′- Di-2-propanoic acid against breast cancer (MDA-MB-231) and colon cancer (HCT-116 and SW-480) cell lines. Maced. J. Chem. Chem. Eng., 2014, 33(1), 53-58.
[http://dx.doi.org/10.20450/mjcce.2014.148]
[35]
Stojković, D.L.; Jevtić, V.V.; Radić, G.P.; Đačić, D.S.; Ćurčić, M.G.; Marković, S.D.; Đinović, V.M.; Petrović, V.P.; Trifunović, S.R. Stereospecific ligands and their complexes. Part XII. Synthesis, characterization and in vitro antiproliferative activity of platinum(IV) complexes with some O,O′-Dialkyl Esters of (S,S)-Ethylenediamine-N, N′-Di-2-propanoic acid against colon cancer (HCT-116) and breast cancer (MDA-MB-231) cell lines. J. Mol. Struct., 2014, 1062(1), 21-28.
[http://dx.doi.org/10.1016/j.molstruc.2014.01.020]
[36]
Pantelić, N.; Zmejkovski, B.B.; Trifunović-Macedoljan, J.; Savić, A.; Stanković, D.; Damjanović, A.; Juranić, Z.; Kaluđerović, G.N.; Sabo, T.J. Gold(III) complexes with esters of cyclohexyl-functionalized ethylenediamine-N,N′-diacetate. J. Inorg. Biochem., 2013, 128, 146-153.
[http://dx.doi.org/10.1016/j.jinorgbio.2013.08.002] [PMID: 23988849]
[37]
Zmejkovski, B.B.; Savić, A.; Poljarević, J.; Pantelić, N.; Aranđelović, S.; Radulović, S.; Grgurić-Šipka, S.; Kaluđerović, G.N.; Sabo, T.J. Synthesis, characterization and in vitro antitumor activity of new palladium(II) complexes with (S,S)-R2edda-type esters. Polyhedron, 2014, 80(80), 106-111.
[http://dx.doi.org/10.1016/j.poly.2014.02.026]
[38]
Mojić, M.; Savić, A.; Arion, V.B.; Bulatović, M.; Poljarević, J.M.; Miljković, D.; Sabo, T.J.; Mijatović, S.; Maksimović-Ivanić, D.; Grgurić-Šipka, S. Synthesis, X-Ray structure and strong in vitro cytotoxicity of novel organoruthenium complexes. J. Organomet. Chem., 2014, 749, 142-149.
[http://dx.doi.org/10.1016/j.jorganchem.2013.08.041]
[39]
Lazić, J.M.; Vucićević, L.; Grgurić-Sipka, S.; Janjetović, K.; Kaluderović, G.N.; Misirkić, M.; Gruden-Pavlović, M.; Popadić, D.; Paschke, R.; Trajković, V.; Sabo, T.J. Synthesis and in vitro anticancer activity of octahedral platinum(IV) complexes with cyclohexyl-functionalized ethylenediamine-N,N′-diacetate-type ligands. ChemMedChem, 2010, 5(6), 881-889.
[http://dx.doi.org/10.1002/cmdc.201000058] [PMID: 20408161]
[40]
Misirlić Denčić, S.; Poljarević, J.; Isakovic, A.M.; Marković, I.; Sabo, T.J.; Grgurić-Šipka, S. Antileukemic action of novel diamine Pt(II) halogenido complexes: Comparison of the representative novel Pt(II) with corresponding Pt(IV) complex. Chem. Biol. Drug Des., 2017, 90(2), 262-271.
[http://dx.doi.org/10.1111/cbdd.12945] [PMID: 28102932]
[41]
Savić, A.; Dulović, M.; Poljarević, J.M.; Misirlić-Denčić, S.; Jovanović, M.; Bogdanović, A.; Trajković, V.; Sabo, T.J.; Grgurić-Šipka, S.; Marković, I. Synthesis and in vitro anticancer activity of ruthenium-cymene complexes with cyclohexyl-functionalized ethylenediamine-N,N′-diacetate-type ligands. ChemMedChem, 2011, 6(10), 1884-1891.
[http://dx.doi.org/10.1002/cmdc.201100232] [PMID: 21805645]
[42]
Kaludjerović, G.N.; Miljković, D.; Momcilović, M.; Djinović, V.M.; Mostarica Stojković, M.; Sabo, T.J.; Trajković, V. Novel platinum(IV) complexes induce rapid tumor cell death in vitro. Int. J. Cancer, 2005, 116(3), 479-486.
[http://dx.doi.org/10.1002/ijc.21080] [PMID: 15818622]
[43]
Mihajlović, L.E.; Savić, A.; Poljarević, J.; Vučković, I.; Mojić, M.; Bulatović, M.; Maksimović-Ivanić, D.; Mijatović, S.; Kaluđerović, G.N.; Stošić-Grujičić, S.; Miljković, Đ.; Grgurić-Šipka, S.; Sabo, T.J. Novel methylene modified cyclohexyl ethylenediamine-N,N′-diacetate ligands and their platinum(IV) complexes. Influence on biological activity. J. Inorg. Biochem., 2012, 109, 40-48.
[http://dx.doi.org/10.1016/j.jinorgbio.2012.01.012] [PMID: 22369771]
[44]
Zmejkovski, B.B.; Kaluderović, G.N.; Gómez-Ruiz, S.; Žižak, Z.; Steinborn, D.; Schmidt, H.; Paschke, R.; Juranić, Z.D.; Sabo, T.J. Palladium(II) complexes with R2edda-derived ligands. Part II. Synthesis, characterization and in vitro antitumoral studies of R2eddip esters and palladium(II) complexes. Eur. J. Med. Chem., 2009, 44(9), 3452-3458.
[http://dx.doi.org/10.1016/j.ejmech.2009.02.002] [PMID: 19272676]
[45]
Pantelić, N.; Stanojković, T.P.; Zmejkovski, B.B.; Sabo, T.J.; Kaluđerović, G.N. In vitro anticancer activity of gold(III) complexes with some esters of (S,S)-ethylenediamine-N,N′-di-2-propanoic acid. Eur. J. Med. Chem., 2015, 90, 766-774.
[http://dx.doi.org/10.1016/j.ejmech.2014.12.019] [PMID: 25528331]
[46]
Pantelić, N.; Zmejkovski, B.B.; Kolundžija, B.; Crnogorac, M.Đ.; Vujić, J.M.; Dojčinović, B.; Trifunović, S.R.; Stanojković, T.P.; Sabo, T.J.; Kaluđerović, G.N. In vitro antitumor activity, metal uptake and reactivity with ascorbic acid and BSA of some gold(III) complexes with N,N′-ethylenediamine bidentate ester ligands. J. Inorg. Biochem., 2017, 172, 55-66.
[http://dx.doi.org/10.1016/j.jinorgbio.2017.04.001] [PMID: 28433833]
[47]
Vujić, J.M.; Cvijović, M.; Kaluderović, G.N.; Milovanović, M.; Zmejkovski, B.B.; Volarević, V.; Arsenijević, N.; Sabo, T.J.; Trifunović, S.R. Palladium(II) complexes with R(2)edda derived ligands. Part IV. O,O′-dialkyl esters of (S,S)-ethylenediamine-N,N′-di-2-(4-methyl)-pentanoic acid dihydrochloride and their palladium(II) complexes: synthesis, characterization and in vitro antitumoral activity against chronic lymphocytic leukemia (CLL) cells. Eur. J. Med. Chem., 2010, 45(9), 3601-3606.
[http://dx.doi.org/10.1016/j.ejmech.2010.05.005] [PMID: 20570025]
[48]
Pantelić, N.; Zmejkovski, B.; Marković, D.; Vujić, J.; Stanojković, T.; Sabo, T.; Kaluđerović, G. Synthesis, Characterization, and cytotoxicity of a novel gold(III) complex with O,O′-Diethyl ester of ethylenediamine-N,N′-Di-2-(4-Methyl)pentanoic acid. Metals (Basel), 2016, 6(10), 226.
[http://dx.doi.org/10.3390/met6090226]
[49]
Djinovic, V.M.; Todorovic, T.; Zizak, Z.; Sabo, T.J.; Juranic, Z.D. Ru(III) Complexes derived from N -methyl derivatives of glycine and 1,3-propylenediamine-N,N′-diacetato ligands and their activities against HeLa, K562 cell lines and human PBMC. J. Coord. Chem., 2009, 62(2), 328-336.
[http://dx.doi.org/10.1080/00958970802233128]
[50]
El-ghamry, H.A.; Masaoka, S.; Sakai, K. Hydrogen-bonded frameworks of propylenediamine-N,N′-Diacetic acid Pt(II) complexes, synthesis, structural characterization, and antitumor activity. J. Coord. Chem., 2014, 67(6), 943-955.
[http://dx.doi.org/10.1080/00958972.2014.900550]
[51]
Savić, A.; Filipović, L.; Aranđelović, S.; Dojčinović, B.; Radulović, S.; Sabo, T.J.; Grgurić-Šipka, S. Synthesis, characterization and cytotoxic activity of novel platinum(II) iodido complexes. Eur. J. Med. Chem., 2014, 82, 372-384.
[http://dx.doi.org/10.1016/j.ejmech.2014.05.060] [PMID: 24927057]
[52]
Ranaldo, R.; Margiotta, N.; Intini, F.P.; Pacifico, C.; Natile, G. Conformer distribution in (cis-1,4-DACH)bis(guanosine-5′-phosphate)platinum(II) adducts: a reliable model for DNA adducts of antitumoral cisplatin. Inorg. Chem., 2008, 47(7), 2820-2830.
[http://dx.doi.org/10.1021/ic702202x] [PMID: 18284193]
[53]
Kasparkova, J.; Suchankova, T.; Halamikova, A.; Zerzankova, L.; Vrana, O.; Margiotta, N.; Natile, G.; Brabec, V. Cytotoxicity, cellular uptake, glutathione and DNA interactions of an antitumor large-ring Pt II chelate complex incorporating the cis-1,4-diaminocyclohexane carrier ligand. Biochem. Pharmacol., 2010, 79(4), 552-564.
[http://dx.doi.org/10.1016/j.bcp.2009.09.019] [PMID: 19782655]
[54]
Yin, R.; Gou, S.; Liu, X.; Lou, L. Antitumor activities and interaction with DNA of oxaliplatin-type platinum complexes with linear or branched alkoxyacetates as leaving groups. J. Inorg. Biochem., 2011, 105(8), 1095-1101.
[http://dx.doi.org/10.1016/j.jinorgbio.2011.05.005] [PMID: 21726773]
[55]
Al-Jaroudi, S.S.; Fettouhi, M.; Wazeer, M.I.M.; Isab, A.A.; Altuwaijri, S. Synthesis, characterization and cytotoxicity of new gold(III) complexes with 1,2-diaminocyclohexane: influence of stereochemistry on antitumor activity. Polyhedron, 2013, 50(1), 434-442.
[http://dx.doi.org/10.1016/j.poly.2012.11.034]
[56]
Al-Jaroudi, S.S. Monim-ul-Mehboob, M.; Altaf, M.; Fettouhi, M.; Wazeer, M.I.M.; Altuwaijri, S.; Isab, A.A. Synthesis, spectroscopic characterization, X-Ray structure and electrochemistry of new bis(1,2-diaminocyclohexane)gold (III) chloride compounds and their anticancer activities against PC3 and SGC7901 cancer cell lines. New J. Chem., 2014, 38(7), 3199-3211.
[http://dx.doi.org/10.1039/C3NJ01624B]
[57]
Al-Jaroudi, S.S.; Altaf, M.; Al-Saadi, A.A.; Kawde, A.N.; Altuwaijri, S.; Ahmad, S.; Isab, A.A. Synthesis, characterization and theoretical calculations of (1,2-diaminocyclohexane)(1,3-diaminopropane)gold(III) chloride complexes: in vitro cytotoxic evaluations against human cancer cell lines. Biometals, 2015, 28(5), 827-844.
[http://dx.doi.org/10.1007/s10534-015-9869-1] [PMID: 26099502]
[58]
Sun, Y.; Gou, S.; Liu, F.; Yin, R.; Fang, L. Synthesis, in vitro cytotoxicity, and interaction with DNA of platinum(II) complexes with N-monocycloalkyl derivatives of 1R,2R-diaminocyclohexane as carrier ligands. ChemMedChem, 2012, 7(4), 642-649.
[http://dx.doi.org/10.1002/cmdc.201100467] [PMID: 22247027]
[59]
Xu, G.; Zhao, J.; Gou, S.; Pang, J. Antitumor platinum(II) complexes of N-cyclobutyl-1R,2R-diaminocyclohexane with dicarboxylates as leaving groups. Bioorg. Med. Chem. Lett., 2015, 25(2), 221-224.
[http://dx.doi.org/10.1016/j.bmcl.2014.11.069] [PMID: 25499430]
[60]
Wang, Z.; Yu, H.; Gou, S.; Chen, F.; Fang, L. Design, synthesis, and biological features of platinum(II) complexes with rigid steric hindrance. Inorg. Chem., 2016, 55(9), 4519-4528.
[http://dx.doi.org/10.1021/acs.inorgchem.6b00361] [PMID: 27074104]
[61]
Gao, J.; Liu, Y.G.; Zhou, Y.; Zingaro, R.A. Chiral salicyl diamines: potent anticancer molecules. ChemMedChem, 2007, 2(12), 1723-1729.
[http://dx.doi.org/10.1002/cmdc.200700049] [PMID: 17943711]
[62]
Morales, F.; Ramírez, A.; Morata-Tarifa, C.; Navarro, S.A.; Marchal, J.A.; Campos, J.M.; Conejo-García, A. Antitumoral activity of 1,2-diaminocyclohexane derivatives in breast, colon and skin human cancer cells. Future Med. Chem., 2017, 9(3), 293-302.
[http://dx.doi.org/10.4155/fmc-2016-0212] [PMID: 28176540]
[63]
Gao, J.; Liu, Y.G.; Zingaro, R.A. Cytotoxic activities, cellular uptake, gene regulation, and optical imaging of novel platinum(II) complexes. Chem. Res. Toxicol., 2009, 22(10), 1705-1712.
[http://dx.doi.org/10.1021/tx900180v] [PMID: 19694485]
[64]
Matos, C.P.; Valente, A.; Marques, F.; Adão, P.; Paula Robalo, M.; de Almeida, R.F.M.; Pessoa, J.C.; Santos, I.; Helena Garcia, M.; Tomaz, A.I. New polydentate ru(III)-salan complexes: synthesis, characterization, anti-tumour activity and interaction with human serum proteins. Inorg. Chim. Acta, 2013, 394(394), 616-626.
[http://dx.doi.org/10.1016/j.ica.2012.09.026]
[65]
Galanski,, M.; Yasemi, A.; Jakupec, M. A. Graf v. Keyserlingk,N.; Keppler, B.K. Synthesis, cytotoxicity, and structure-activity relationships of new oxaliplatin derivatives. Monatshefte fur Chemie - Chem. Mon,, 2005, 136(5), 693-700.
[http://dx.doi.org/10.1007/s00706-004-0241-3]
[66]
Sun, Y.; Yin, R.; Gou, S. Zhaojian, Antitumor platinum(II) complexes of N-monoalkyl-1R, 2R-diaminocyclohexane derivatives with alkyl groups as hindrance. J. Inorg. Biochem., 2012, 112, 68-76.
[http://dx.doi.org/10.1016/j.jinorgbio.2012.03.003] [PMID: 22561544]
[67]
Dehand, J.; Jordanov, J. Anti-tumour activity of heavy transition metal complexes against hepatoma cells. Chem. Biol. Interact., 1975, 11(6), 605-609.
[http://dx.doi.org/10.1016/0009-2797(75)90035-6] [PMID: 172246]
[68]
Kidani, Y.; Asano, Y.; Noji, M. Synthesis of platinum(II) complexes of 4-substituted o-phenylenediamine derivatives and determination of their antitumor activity. Chem. Pharm. Bull. (Tokyo), 1979, 27(11), 2577-2581.
[http://dx.doi.org/10.1248/cpb.27.2577] [PMID: 527142]
[69]
Dullin, A.; Dufrasne, F.; Gelbcke, M.; Gust, R. Synthesis and cytotoxicity of enantiomerically pure [1,2-diamino-1-(4-fluorophenyl)-3-methylbutane]platinum(II) complexes. ChemMedChem, 2006, 1(6), 644-653.
[http://dx.doi.org/10.1002/cmdc.200600032] [PMID: 16892405]
[70]
Yang, Q.; Chang, J.; Song, J.; Qian, M.T.; Yu, J.M.; Sun, X. Synthesis and in vitro antitumor activity of novel iridium(III) complexes with enantiopure C2-symmetrical vicinal diamine ligands. Bioorg. Med. Chem. Lett., 2013, 23(16), 4602-4607.
[http://dx.doi.org/10.1016/j.bmcl.2013.06.024] [PMID: 23849808]
[71]
Pérez-Cabré, M.; Cervantes, G.; Moreno, V.; Prieto, M.J.; Pérez, J.M.; Font-Bardia, M.; Solans, X. Pd(II) and Pt(II) complexes with aromatic diamines: study of their interaction with DNA. J. Inorg. Biochem., 2004, 98(3), 510-521.
[http://dx.doi.org/10.1016/j.jinorgbio.2003.12.022] [PMID: 14987853]
[72]
Bugarcic, T.; Habtemariam, A.; Deeth, R.J.; Fabbiani, F.P.A.; Parsons, S.; Sadler, P.J. Ruthenium(II) arene anticancer complexes with redox-active diamine ligands. Inorg. Chem., 2009, 48(19), 9444-9453.
[http://dx.doi.org/10.1021/ic9013366] [PMID: 19780621]
[73]
Habtemariam, A.; Melchart, M.; Fernández, R.; Parsons, S.; Oswald, I.D.H.; Parkin, A.; Fabbiani, F.P.A.; Davidson, J.E.; Dawson, A.; Aird, R.E.; Jodrell, D.I.; Sadler, P.J. Structure-activity relationships for cytotoxic ruthenium(II) arene complexes containing N,N-, N,O-, and O,O-chelating ligands. J. Med. Chem., 2006, 49(23), 6858-6868.
[http://dx.doi.org/10.1021/jm060596m] [PMID: 17154516]
[74]
Taguchi, T.; Kurata, S.; Ohashi, M. Effects of polyamines on DNA synthesis using various subcellular DNA polymerases extracted from normal rat liver, tumour-bearing rat liver, and tumour cells. Cell Biochem. Funct., 2001, 19(1), 19-26.
[http://dx.doi.org/10.1002/cbf.894] [PMID: 11223867]
[75]
Navarro-Ranninger, C.; Pérez, J.M.; Zamora, F.; González, V.M.; Masaguer, J.R.; Alonso, C. Palladium (II) compounds of putrescine and spermine. Synthesis, characterization, and DNA-binding and antitumor properties. J. Inorg. Biochem., 1993, 52(1), 37-49.
[http://dx.doi.org/10.1016/0162-0134(93)85621-E] [PMID: 8228977]
[76]
Navarro-Ranninger, C.; Ochoa, P.A.; Pérez, J.M.; González, V.M.; Masaguer, J.R.; Alonso, C. Platinum (II) and (IV) spermidine complexes. Synthesis, characterization, and biological studies. J. Inorg. Biochem., 1994, 53(3), 177-190.
[http://dx.doi.org/10.1016/0162-0134(94)80003-0] [PMID: 8133254]
[77]
Schreier, S.; Malheiros, S.V.P.; de Paula, E. Surface active drugs: self-association and interaction with membranes and surfactants. Physicochemical and biological aspects. Biochim. Biophys. Acta, 2000, 1508(1-2), 210-234.
[http://dx.doi.org/10.1016/S0304-4157(00)00012-5] [PMID: 11090827]
[78]
Jurisevic, M.; Radosavljevic, G.; Arsenijevic, A.; Milovanovic, M.; Gajovic, N.; Djordjevic, D.; Milovanovic, J.; Stojanovic, B.; Ilic, A.; Sabo, T. Platinum complexes with EDDA (Ethylenediamine-N,N-Diacetate) ligands as potential anticancer agents. Serb. J. Exp. Clin. Res., 2016, 17(4), 285-295.
[http://dx.doi.org/10.1515/sjecr-2016-0042]
[79]
Zmejkovski, B.B.; Sabo, T.J.; Kaluđerović, G.N. Palladium(II) complexes with R2edda derived ligands. Part VI. O,O′-Diisopropyl Ester of N,N′-1,2-Ethanediylbis-L-Leucine, dihydrochloride dihydrate and its palladium(II) complex:synthesis and characterization. J. Serb. Chem. Soc., 2013, 78(8), 1171-1176.
[http://dx.doi.org/10.2298/JSC130113021Z]
[80]
Kaluderović, G.N.; Hernández-Corroto, E.; Brandt, W.; Zmejkovski, B.B.; Gómez-Ruiz, S. Palladium(II) complexes with R2edda-derived ligands. J. Coord. Chem., 2016, 69(8), 1337-1345.
[http://dx.doi.org/10.1080/00958972.2016.1168519]
[81]
Dimitrijević, D.P.; Radić, G.P.; Jevtić, V.V.; Mišić, M.; Baskić, D.; Trifunović, S.R. Stereospecific ligands and their complexes. XX. Synthesis, characterization and antimicrobial activity of Palladium(II) complexes with some alkyl esters of Ethylenediamine-N,N′-Di-S,S-(2,2′-Dibenzyl)Acetic Acid. J. Mol. Struct., 2014, 1071, 128-132.
[http://dx.doi.org/10.1016/j.molstruc.2014.05.008]
[82]
Sabo, T.J.; Kaluđerović, G.N.; Grgurić-Šipka, S.R.; Heinemann, F.W.; Trifunović, S.R. Complex compounds of platinum(IV) and O,O-Dialkyl-Ethylenediamine-N,N′-Di-3-Propanoate Ligands. A structural evidence for geometry of hydrolytic product of some esters. Inorg. Chem. Commun., 2004, 7(2), 241-244.
[http://dx.doi.org/10.1016/j.inoche.2003.11.007]
[83]
Kaluđerović, G.N.; Schmidt, H.; Steinborn, D.; Sabo, T.J. From synthesis to antitumoral activity of platinum(II) and platinum(IV) complexes with bis(Carboxyalkylamino) Ethane and-Propane Ligands in: Inorganic biochemistry: research progress; Hughes, J.G; Robinson, A.J., Ed.; Nova Science Publishers: Hauppauge, New York, 2008, pp. 305-326.
[84]
Miljković, D.; Poljarević, J.M.; Petković, F.; Blaževski, J.; Momčilović, M.; Nikolić, I.; Saksida, T.; Stošić-Grujičić, S.; Grgurić-Šipka, S.; Sabo, T.J. Novel octahedral Pt(IV) complex with di-n-propyl-(S,S)-ethylenediamine-N,N′-di-2-(3-cyclohexyl)propanoato ligand exerts potent immunomodulatory effects. Eur. J. Med. Chem., 2012, 47(1), 194-201.
[http://dx.doi.org/10.1016/j.ejmech.2011.10.042] [PMID: 22071257]
[85]
Choy, H.; Park, C.; Yao, M. Current status and future prospects for satraplatin, an oral platinum analogue. Clin. Cancer Res., 2008, 14(6), 1633-1638.
[http://dx.doi.org/10.1158/1078-0432.CCR-07-2176] [PMID: 18347164]
[86]
Stojković, D.L.; Jevtić, V.V.; Radić, G.P.; Potočňák, I.; Trifunović, S.R. Stereospecific Ligands and Their Complexes. Part XVII. Synthesis and characterization of ethylenediamine-N,N′-Di-S,S-2-(3-Methyl)butanoic acid and its platinum(IV) complex with bromido ligands. Crystal Structure of s-Cis-[PtBr2(S,S-Eddv)]·H2O. J. Mol. Struct., 2014, 1065-1066, 16-20.
[http://dx.doi.org/10.1016/j.molstruc.2014.02.030]
[87]
Radić, G.P.; Glođović, V.V.; Kaluđerović, G.N.; Heinemann, F.W.; Trifunović, S.R. Palladium(II) complexes with R2edda-derived ligands. Part V. Reaction of O,O′-Diethyl-(S,S)-Ethylenediamine-N,N′-Di-2-(3-Methyl)Butanoate with K2[PdCl4. Transit. Met. Chem., 2011, 36(4), 331-336.
[http://dx.doi.org/10.1007/s11243-011-9473-3]
[88]
Đinović, V.M.; Bogdanović, G.A.; Novaković, S.; Sabo, T.J. Synthesis and crystal ctructure of trans -dichloro(1,3-Propylenediamine- n,N′ -Diacetato)Platinum(IV) Monohydrate. J. Coord. Chem., 2004, 57(7), 535-541.
[http://dx.doi.org/10.1080/00958970410001671110]
[89]
Kostova, I. Platinum complexes as anticancer agents. Recent Patents Anticancer Drug Discov., 2006, 1(1), 1-22.
[http://dx.doi.org/10.2174/157489206775246458] [PMID: 18221023]
[90]
Stein, A.; Arnold, D. Oxaliplatin: a review of approved uses. Expert Opin. Pharmacother., 2012, 13(1), 125-137.
[http://dx.doi.org/10.1517/14656566.2012.643870] [PMID: 22149372]
[91]
Djeković, A.; Petrović, B.; Bugarčić, Ž.D.; Puchta, R.; van Eldik, R. Kinetics and mechanism of the reactions of Au(III) complexes with some biologically relevant molecules. Dalton Trans., 2012, 41(13), 3633-3641.
[http://dx.doi.org/10.1039/c2dt11843b] [PMID: 22318647]
[92]
Wong, E.; Giandomenico, C.M. Current status of platinum-based antitumor drugs. Chem. Rev., 1999, 99(9), 2451-2466.
[http://dx.doi.org/10.1021/cr980420v] [PMID: 11749486]
[93]
Misset, J.L.; Bleiberg, H.; Sutherland, W.; Bekradda, M.; Cvitkovic, E. Oxaliplatin clinical activity: a review. Crit. Rev. Oncol. Hematol., 2000, 35(2), 75-93.
[http://dx.doi.org/10.1016/S1040-8428(00)00070-6] [PMID: 10936465]
[94]
Zhao, J.; Gou, S.; Xu, G.; Cheng, L. Antitumor platinum(II) complexes of N-monoalkyl 1R,2R-diamino-cyclohexanes with 3-(nitrooxy)cyclobutane-1,1-dicarboxylate as a leaving group. Eur. J. Med. Chem., 2014, 85, 408-417.
[http://dx.doi.org/10.1016/j.ejmech.2014.08.007] [PMID: 25108080]
[95]
Hu, J.; Wu, T.M.; Li, H.Z.; Zuo, Z.P.; Zhao, Y.L.; Yang, L. The synthesis, structure-toxicity relationship of cisplatin derivatives for the mechanism research of cisplatin-induced nephrotoxicity. Bioorg. Med. Chem. Lett., 2017, 27(15), 3591-3594.
[http://dx.doi.org/10.1016/j.bmcl.2017.04.077] [PMID: 28579329]

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