38780-40-4Relevant articles and documents
One-Pot Synthesis of New Organometallic Compounds with Platinum-Carbon Bond
Barbanente, Alessandra,Intini, Francesco P.,Margiotta, Nicola,Natile, Giovanni,Pacifico, Concetta
, (2020)
Organometallic compounds of platinum containing ortho metalated para-nitro-benzamidate or 1-naphthalene-methylamine have been prepared by one-pot synthesis. The para-nitro-benzamidate [Pt{K2C,N-pNO2-C6H4C(O)NH}(R,R-DACH)] (compound 2) was obtained starting from [PtCl2(R,R-DACH)] and para-nitro-benzonitrile, which, in the reaction conditions, hydrolyzes to the corresponding amide and forms the dinuclear intermediate [Pt2{μ-N,O-pNO2-C6H4C(O)NH}2(R,R-DACH)2]SO4 (compound 1·SO4) with HH or HT arrangement of the two bridging amidato ligands. Compound 1·SO4, kept at 90 °C for few hours, transforms into 2. The ortho-metalated PtII derivative with 1-naphthalene-methylamine [PtCl{K2C,N-C10H6CH2NH2}(DMSO)] (3) was obtained by direct reaction of [PtCl2(DMSO)2] with the amine. Unlike compound 2 that has no labile ligands, compound 3 has Cl and DMSO ligands that can be released, allowing the formation of cross-links with DNA. Oxidation of 3 to the PtIV counterpart was performed with PhICl2 (compound 4). Unexpectedly, although six-coordinate complexes of PtIV are considered to be inert, 4 underwent spontaneous isomerization from the mer to the fac isomer. All compounds have been fully characterized by multinuclear NMR spectroscopy, which has enabled complete assignment of all proton resonances. In the case of compound 2, a single-crystal X-ray investigation was also performed, showing, with the only exception of the puckered cyclohexane ring, a complete planarity of the complex frame, which could favor an intercalative interaction with DNA.
Synthesis, cytotoxic activity and DNA interaction studies of new dinuclear platinum(ii) complexes with an aromatic 1,5-naphthyridine bridging ligand: DNA binding mode of polynuclear platinum(ii) complexes in relation to the complex structure
Konovalov, Bata,?ivkovi?, Marija D.,Milovanovi?, Jelena Z.,Djordjevi?, Dragana B.,Arsenijevi?, Aleksandar N.,Vasi?, Ivana R.,Janji?, Goran V.,Franich, Andjela,Manojlovi?, Dragan,Skrivanj, Sandra,Milovanovi?, Marija Z.,Djuran, Milo? I.,Rajkovi?, Sne?ana
, p. 15091 - 15102 (2018/11/10)
The synthesis, spectroscopic characterization, cytotoxic activity and DNA binding evaluation of seven new dinuclear platinum(ii) complexes Pt1-Pt7, with the general formula [{Pt(L)Cl}2(μ-1,5-nphe)](ClO4)2 (1,5-nphe is 1,5-naphthyridine; while L is two ammines (Pt1) or one bidentate coordinated diamine: ethylenediamine (Pt2), (±)-1,2-propylenediamine (Pt3), trans-(±)-1,2-diaminocyclohexane (Pt4), 1,3-propylenediamine (Pt5), 2,2-dimethyl-1,3-propylenediamine (Pt6), and 1,3-pentanediamine (Pt7)), were reported. In vitro cytotoxic activity of these complexes was evaluated against three tumor cell lines, murine colon carcinoma (CT26), murine mammary carcinoma (4T1) and murine lung cancer (LLC1) and two normal cell lines, murine mesenchymal stem cells (MSC) and human fibroblast (MRC-5) cells. The results of the MTT assay indicate that all investigated complexes have almost no cytotoxic effects on 4T1 and very low cytotoxicity toward LLC1 cell lines. In contrast to the effects on LLC1 and 4T1 cells, complexes Pt1 and Pt2 had significant cytotoxic activity toward CT26 cells. Complex Pt1 had a much lower IC50 value for activity on CT26 cells compared with cisplatin. In comparison with cisplatin, all dinuclear Pt1-Pt7 complexes showed lower cytotoxicity toward normal MSC and MRC-5 cells. In order to measure the amount of platinum(ii) complexes taken up by the cells, we quantified the cellular platinum content using inductively coupled plasma mass spectrometry (ICP-QMS). Molecular docking studies performed to evaluate the potential binding mode of dinuclear platinum(ii) complexes Pt1-Pt7 and their aqua derivatives W1-W7, respectively, at the double stranded DNA showed that groove spanning and backbone tracking are the most stable binding modes.
Synthetic method of oxaliplatin
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Paragraph 0011; 0017; 0022; 0027, (2017/08/31)
The invention discloses a synthetic method of oxaliplatin. The synthetic method comprises the following steps: firstly, taking potassium chloroplatinite and (1R,2R)-1,2-cyclohexanediamine, putting the substances into water, keeping a mixed solution in dark place and reacting the mixed solution under the conditions that the temperature is 35 to 45 DEG C and microwave is 200 to 500W to obtain cis-dichloro(1R,2R)-1,2-cyclohexanediamineplatinum; secondly, dissolving a product obtained in the first step into water, adding silver sulfate, keeping a mixed solution in the dark place, stirring the mixed solution under the conditions that the temperature is 35 to 50 DEG C and microwave is 200 to 400W and then filtering; thirdly, taking filtrate in the second step, adding tetraethylammonium lodide and activated carbon, stirring and filtering; fourthly, taking filtrate in the third step, first adding oxalic acid and Ba(OH)2.8H2O in the stirring process, stirring for 2 to 3 hours under the condition of keeping in the dark place, filtering, and evaporating and refining the filtrate to obtain the oxaliplatin. By using microwave reaction conditions, the efficiency is improved, reaction time is shortened, production period is shortened, and the production cost is reduced; the purity and the yield of a product are higher.
