16893-05-3Relevant articles and documents
Oxidative halogenation of cisplatin and carboplatin: Synthesis, spectroscopy, and crystal and molecular structures of Pt(iv) prodrugs
Johnstone, Timothy C.,Alexander, Sarah M.,Wilson, Justin J.,Lippard, Stephen J.
, p. 119 - 129 (2014)
A series of Pt(iv) prodrugs has been obtained by oxidative halogenation of either cisplatin or carboplatin. Iodobenzene dichloride is a general reagent that cleanly provides prodrugs bearing axial chlorides without the need to prepare intervening Pt(iv) intermediates or handle chlorine gas. Elemental bromine and iodine afford Pt(iv) compounds as well, although in the case of the iodine-mediated oxidation of carboplatin, an amido-bridged Pt(iv) side product also formed. A detailed analysis of the changes in spectroscopic and structural parameters induced by varying the axial halide is presented. A number of recurring motifs are observed in the solid state structures of these compounds. This journal is
Halogenated PtIV Complexes from N-Halosuccinimide Oxidation of PtII Antitumor Drugs: Synthesis, Mechanistic Investigation, and Cytotoxicity
Xu, Zoufeng,Li, Cai,Tong, Zixuan,Ma, Lili,Tse, Man-Kit,Zhu, Guangyu
, p. 1706 - 1712 (2017)
Compared with square-planar PtII drugs, PtIV-based anticancer prodrugs are relatively inert under physiological conditions and can be activated after entering cells. The two axial ligands in PtIV complexes provide an opportunity to further functionalize these prodrugs. In recent years, much effort has been devoted to developing new PtIV-based anticancer prodrugs with higher cytotoxicity but fewer side effects. New synthetic methods, however, are intensely desired for structurally diversified and biologically distinct PtIV complexes. Herein, we utilize N-halosuccinimides as oxidants and carry out the oxidation reaction on PtII drugs including cisplatin, carboplatin, and oxaliplatin to obtain halogenated PtIV complexes. The related mechanism of the reaction of N-bromosuccinimide (NBS) with cisplatin in ethanol is thoroughly investigated. N-chlorosuccinimide is also utilized to obtain the respective dichlorinated PtIV complexes. When N-iodosuccinimide reacts with PtII drugs, new PtIV compounds containing iodide and succinimide ligands in the axial position are formed. Cytotoxicity test shows that some of the complexes are active against cisplatin-resistant human ovarian cancer cells. Our study provides a detailed understanding of the reaction mechanism between NBS and cisplatin and offers a more convenient strategy to obtain dichlorinated and new iodinated PtIV anticancer prodrugs.
Discovery and identification of the first platinum anticancer compound
Grimley, Eugene
, (2019)
Irradiation of solutions of the complex ion, [PtCl6]2?, in the presence of NH4+ results in photochemical changes in which the chlorides of the complex are replaced by 1, 2, or more ammonia molecules with the charge decreasing by one for each replacement. These replacements were followed by changes in absorption spectra and electrochromatographic patterns and were isolated by continuous curtain electrochromatography. Each species had unique effects on the bacteriological growth of Escherichia coli. The doubly negative species is a bacteriocide and the singly negative species had little effect on either cell growth or cell division. The neutral species caused significant inhibition of cell division, formed filamentous cells, and was bacteriologically determined to be [PtCl4(NH3)2]. The cis and trans isomers of [PtCl4(NH3)2] were synthesized and tested. Bacteriological studies comparing both isomers of the neutral species showed that the trans isomer had little effect on inhibition of cell growth or cell division, whereas the cis isomer was fully efficient. The starting complex for synthesis of the cis complex, cis-[PtCl2(NH3)2], known medically as cisplatin, was biologically tested and also found to be fully effective in inhibiting cell growth.
CIS-OXOPLATIN FOR TREATING STOMACH CANCER
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Page/Page column 24-25, (2020/01/24)
The invention relates to a pharmaceutical composition comprising cis-oxoplatin, or a salt and/or derivative thereof, for use as a medicament in the treatment and/or preventation of stomach cancer. The invention further relates to the pharmaceutical composition as described for use in the treatment of stomach cancer, wherein the cis-oxoplatin or derivative thereof is administered in a form that is transformed under acidic pH to a tetrachloro-oxoplatin (IV).
Synthesis of pyrophosphatotetraamminediplatinum(II) complex and its transformations in hydrochloric acid solutions
Starkov,Patrushev
, p. 312 - 312 (2008/10/09)
A new method for the synthesis of [Pt2(NH3) 4P2O7] is proposed. Its transformations in a hydrochloric acid medium are described. Nauka/Interperiodica 2007.
Tetraamminecopper(II) hexachloroplatinate(IV) Hemihydrate [Cu(NH3)4][PtCl6] · 0.5H2O: Synthesis and Thermal Transformations
Bol'shakova,Lapkin
, p. 69 - 74 (2008/10/08)
Thermal decomposition of the double heteronuclear complex [Cu(NH3)4][PtCl6] · 0.5H2O is studied. It is shown that the thermal isomerization stage (180°C) associated with migration of ligands and formation of mixed-ligand platinum(IV) and copper(II) complexes is preceded by the removal of adsorbate water. The final products of thermal decomposition in air are the mixture of metal platinum and copper oxide; in argon, platinum-base solid Pt-Cu solution is formed.
Platinum(II) complexes catalyze reactions between platinum(IV) complexes and 9-methylxanthine
Roat, Rosette M.,Jerardi, Maria J.,Kopay, Catherine B.,Heath, Danica C.,Clark, Jessica A.,DeMars, Jessa A.,Weaver, John M.,Bezemer, Ernst,Reedijk, Jan
, p. 3615 - 3621 (2007/10/03)
Reactions between 9-methylxanthine (9-mxan) and platinum(IV) complexes having ammine, organic amine and chloro ligands are speeded up dramatically by additions of small amounts of the analogous platinum(II) complex. Complexes studied include cis-dichlorodiammineplatinum(II) {cis-[Pt(NH3)2Cl2] 1a}, cis-tetrachlorodiammine-platinum(IV) {cis-[Pt(NH3)2Cl4] 1b}, cis-dichloroammine(cyclohexylamine)platinum(II) {cis-[Pt(NH3)(cha)Cl2] 2a}, cis-tetrachloroammine(cyclohexylamine)platinum(IV) {cis-[Pt(NH3)(cha)Cl4] 2b}, chloro(diethylenetriamine)-platinum(II) chloride {[Pt(dien)Cl]Cl 3a} and mer-trichloro(diethylenetriamine)platinum(IV) chloride {mer-[Pt(dien)Cl3]Cl 3b}. For a 10:90 molar ratio of 1a:1b, the half-life for platinum(IV) - 9-mxan product formation is approximately 3 h whereas t1/2 for pure 1b-9-mxan product formation is greater than 90 h, indicating a 30 times rate enhancement upon addition of 10% of the platinum(II) complex. For the 2a:2b pair, an eight-fold rate enhancement is observed over that for pure 2b-9-mxan. This behavior may be related to the chloride bridging mechanism first elucidated for platinum-(II) and -(IV) complexes. Since known platinum-(II) and -(IV) antitumor drugs target nucleobases of DNA to effect cell death in malignant cells, the reactions discussed may shed light on platinum antitumor compound reaction mechanisms.
Effects of Geometric Configuration and Steric Hindrance on Rates and Mechanisms of Oxidation of Diaminedichloroplatinum(II) Complexes by Tetrachloroaurate(III) Ions
Peloso, Arnaldo
, p. 1285 - 1290 (2007/10/02)
The oxidation reactions of trans- and/or cis- by - in the presence of Cl have been kinetically investigated in acetonitrile (R=H,Me,Et,Prn,Pri,Bun,Bui,Bus,But,CH2But,CH2Ph, or cyclo-C6H11).The rate law for the oxidation of the trans complexes consists mainly of a third-order rate term, kc->->, whereas an additiona rate term, ka->->/(1+kb->), operates in the case of the cis complexes.A reaction scheme is proposed.The oxidation rates of both cis and trans complexes appear to be reduced by increasing the steric hindrance of the amine, cis complexes being more sensitive towards changes of steric hindrance than trans analogues.Approximate linear relationships correlate the reactivities (log k) of both cis and trans complexes with an amine steric hindrance parameter.
