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.
作者： Bojana B. Krajčinović , Goran N. Kaluđerović , Dirk Steinborn , Harry Schmidt , Christoph Wagner
DOI: 10.1016/J.JINORGBIO.2007.12.009
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摘要: Abstract Syntheses of two novel ligand precursors O,O′-diisopropyl- (1a) and O,O′-diisobutyl-(S,S)-ethylenediamine-N,N′-di-2-propanoate dihydrochloride monohydrate (1b) the corresponding dichloroplatinum(II) (2a 2b) tetrachloroplatinum(IV) complexes (3a 3b) are described here. The substances were characterized by IR, 1H 13C spectroscopy elemental analysis. Crystal structures determined for 1a platinum(IV) complex, 3a. In vitro antiproliferative activity was against tumor cell lines: human adenocarcinoma HeLa, myelogenous leukemia K562, malignant melanoma Fem-x, rested stimulated normal immunocompetent cells (human peripheral blood mononuclear PBMC cells) using KBR test (Kenacid Blue Dye binding test). IC50(μM) values most active compound 3a were: 30.48 ± 2.54; 12.26 ± 2.60; 13.68 ± 3.22; 80.18 ± 24.07 71.30 ± 21.70, respectively.
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sci-hub.se 参考文章(20)
Joseph N Jolley, Alexander I Yanovsky, Lloyd R Kelland, Kevin B Nolan, Synthesis and antitumour activity of platinum(II) and platinum(IV) complexes containing ethylenediamine-derived ligands having alcohol, carboxylic acid and acetate substituents Journal of Inorganic Biochemistry. ,vol. 83, pp. 91- 100 ,(2001) , 10.1016/S0162-0134(00)00190-2
Barnett Rosenberg, Loretta Van Camp, Eugene B. Grimley, Andrew J. Thomson, The Inhibition of Growth or Cell Division in Escherichia coli by Different Ionic Species of Platinum(IV) Complexes Journal of Biological Chemistry. ,vol. 242, pp. 1347- 1352 ,(1967) , 10.1016/S0021-9258(18)96186-7
N. K. Banda, W. C. Satterfield, A. Dunlap, K. S. Steimer, R. Kurrle, T. H. Finkel, Lack of gp120-induced anergy and apoptosis in chimpanzees is correlated with resistance to AIDS Apoptosis. ,vol. 1, pp. 49- 62 ,(1996) , 10.1007/BF00142078
Dong Wang, Stephen J. Lippard, Cellular processing of platinum anticancer drugs. Nature Reviews Drug Discovery. ,vol. 4, pp. 307- 320 ,(2005) , 10.1038/NRD1691
BARNETT ROSENBERG, LORETTA VAN CAMP, THOMAS KRIGAS, Inhibition of Cell Division in Escherichia coli by Electrolysis Products from a Platinum Electrode Nature. ,vol. 205, pp. 698- 699 ,(1965) , 10.1038/205698A0
Jan Reedijk, Improved understanding in platinium antitumour chemistry Chemical Communications. pp. 801- 806 ,(1996) , 10.1039/CC9960000801
Goran N. Kaluđerović, Vesna M. Đinović, Zorica D. Juranić, Tatjana P. Stanojković, Tibor J. Sabo, 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 Journal of Inorganic Biochemistry. ,vol. 99, pp. 488- 496 ,(2005) , 10.1016/J.JINORGBIO.2004.10.025
Tibor J Sabo, Goran N Kaluđerović, Sanja R Grgurić-Šipka, Frank W Heinemann, Srecko R Trifunović, 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 Inorganic Chemistry Communications. ,vol. 7, pp. 241- 244 ,(2004) , 10.1016/J.INOCHE.2003.11.007
D. B. Haydock, T. P. C. Mulholland, Some derivatives of NN′-biscarboxymethyl- and NN′-bis-(β-carboxyethyl)-ethylenediamine J. Chem. Soc. C. ,vol. 0, pp. 2389- 2395 ,(1971) , 10.1039/J39710002389
Goran N. Kaluderović, Harry Schmidt, Christoph Wagner, Dirk Steinborn, trans,cis-Dibromido[diethyl (ethane-1,2-diyldiimino)diacetate-κ2N,N′]dimethylplatinum(IV) Acta Crystallographica Section E-structure Reports Online. ,vol. 63, ,(2007) , 10.1107/S1600536807029534