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Rhodium(III) and iridium(III) pentamethylcyclopentadienyl complexes with tris(2-carboxyethyl)phosphine, properties and cytostatic activity

Published on Nov 1, 2016in Journal of Organometallic Chemistry2.07
· DOI :10.1016/j.jorganchem.2016.08.005
Hanna Pruchnik10
Estimated H-index: 10
(Wroclaw University of Environmental and Life Sciences),
Małgorzata Latocha12
Estimated H-index: 12
(Medical University of Silesia)
+ 1 AuthorsFlorian P. Pruchnik18
Estimated H-index: 18
(UWr: University of Wrocław)
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Abstract
Abstract New pentamethylcyclopentadienyl complexes [M(C 5 Me 5 )Cl 2 (TCEP)] (M = Rh 1 , M = Ir 2 ) with P(C 2 H 4 COOH) 3 (TCEP) were investigated using IR, 1 H, 13 C, 31 P NMR and ESI-MS spectroscopies. Geometry optimization in the gas phase at the B3LYP/3-21G** level indicated that complex 1 has stable pseudooctahedral structure with large HOMO–LUMO gap. Calculated and experimental IR spectra of 1 agree very well. Cytostatic activity of compounds 1 and 2 was investigated against melanoma and breast tumor cells. Complexes 1 and 2 show very promising activity towards MDA-MB-231 triple negative breast cancer cells.
  • References (38)
  • Citations (1)
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References38
Newest
Published on Mar 1, 2016in Journal of Inorganic Biochemistry3.22
Hanna Pruchnik10
Estimated H-index: 10
(Wroclaw University of Environmental and Life Sciences),
Tadeusz Lis30
Estimated H-index: 30
(UWr: University of Wrocław)
+ 2 AuthorsFlorian P. Pruchnik18
Estimated H-index: 18
(UWr: University of Wrocław)
Abstract Water soluble and air stable P(RCOOH) 3 (R = C 2 H 4 ) (TCEP) is an efficient reducing agent used in biochemistry to break S–S bond in peptides, proteins and other compounds containing S–S bonds. The similarity between the coordination chemistry of Pd(II) and Pt(II) led to the investigations of antitumor activity of palladium(II) compounds however the Pd(II) complexes with TCEP were not investigated. New palladium(II) complexes with (TCEP): trans -[PdCl 2 (TCEP) 2 ] ( 1 ) and trans -[Pd...
Published on Aug 1, 2015in Journal of Organometallic Chemistry2.07
Hanna Pruchnik10
Estimated H-index: 10
(Wroclaw University of Environmental and Life Sciences),
Tadeusz Lis30
Estimated H-index: 30
(UWr: University of Wrocław),
Florian P. Pruchnik18
Estimated H-index: 18
(UWr: University of Wrocław)
Abstract It has recently been found that P(C 2 H 4 COOH) 3 (TCEP), used in the reduction of S–S bonds, promoted reaction of cisplatin with Sp1 zinc finger protein and Cu(I) transporters. However Pt complexes with TCEP were not investigated. New platinum(II) complexes with (TCEP): trans -[PtCl 2 (TCEP) 2 ] ( 1 ) and cis -[PtCl 2 (TCEP) 2 ] · 1.25H 2 O ( 2 ) were fully characterized by IR, 1 H, 13 C, 31 P, 195 Pt NMR and ESI-MS spectroscopic techniques. Structures of trans -[PtCl 2 {P(C 2 H 4 COOD...
Published on Jul 1, 2015in Journal of Organometallic Chemistry2.07
Gajendra Gupta15
Estimated H-index: 15
(UniNE: University of Neuchâtel),
Emmanuel Denoyelle-Di-Muro3
Estimated H-index: 3
(UniNE: University of Neuchâtel)
+ 3 AuthorsBruno Therrien45
Estimated H-index: 45
(UniNE: University of Neuchâtel)
Abstract Two pentamethylcyclopentadienyl (Cp*) rhodium(III) and iridium(III) metalla-prisms of the general formula [(Cp*M) 6 (tpt) 2 (dhnq) 3 ] 6+ (tpt = 2,4,6-tri-(pyridin-4-yl)-1,3,5-triazine, dhnq = 5,8-dihydroxy-1,4-naphthoquinonato; M = Rh, [ 1 ] 6+ ; M = Ir, [ 2 ] 6+ ) have been synthesized by mixing in methanol the neutral dinuclear complexes (Cp*M) 2 (dhnq)Cl 2 (M = Rh, Ir), AgCF 3 SO 3 and tpt. In a similar fashion, the addition of porphin during the formation of [ 1 ] 6+ and [ 2 ] 6+ l...
Published on Jun 8, 2015in Organometallics4.10
Adam J. Millett1
Estimated H-index: 1
,
Abraha Habtemariam37
Estimated H-index: 37
+ 2 AuthorsPeter J. Sadler89
Estimated H-index: 89
We report the synthesis, characterization, and antiproliferative activity of 15 iridium(III) half-sandwich complexes of the type [(η5-Cp*)Ir(2-(R′-phenyl)-R-pyridine)Cl] bearing either an electron-donating (−OH, −CH2OH, −CH3) or electron-withdrawing (−F, −CHO, −NO2) group at various positions on the 2-phenylpyridine (2-PhPy) chelating ligand giving rise to six sets of structural isomers. The X-ray crystal structures of [(η5-Cp*)Ir(2-(2′-fluorophenyl)pyridine)Cl] (1) and [(η5-Cp*)Ir(2-(4′-fluorop...
Published on Sep 1, 2014in Inorganica Chimica Acta2.43
Mahesh Kalidasan4
Estimated H-index: 4
(NEHU: North Eastern Hill University),
Scott Forbes6
Estimated H-index: 6
(McMaster University)
+ 4 AuthorsMohan Rao Kollipara17
Estimated H-index: 17
(NEHU: North Eastern Hill University)
Abstract Mononuclear cationic half-sandwich arene Ru(II) and Cp ∗ Rh(III)/Cp ∗ Ir(III) compounds with the general formula [(η 6 -arene)Ru(L)Cl] + and [Cp ∗ M(L)Cl] + have been isolated by the reaction of bithiazole ligands {2,2′-dimethyl-4,4′-bithiazole ( dm4bt ), 2,2′-diamino-4,4′-bithiazole ( da4bt ), and 2,2′-diphenyl-4,4′-bithiazole ( dp4bt )} with the precursor compounds [(η 6 -arene)Ru(μ-Cl)Cl] 2 (arene = C 6 H 6 , p - i PrC 6 H 4 Me or C 6 Me 6 ) and [Cp ∗ M(μ-Cl)Cl] 2 (M = Rh, Ir). These...
Published on May 1, 2014in Journal of Inorganic Biochemistry3.22
Orsolya Dömötör11
Estimated H-index: 11
(University of Szeged),
Sabine Aicher1
Estimated H-index: 1
(University of Vienna)
+ 7 AuthorsÉva A. Enyedy24
Estimated H-index: 24
(University of Szeged)
Abstract The reaction of the dimer [Rh III (pentamethylcyclopentadienyl)(μ-Cl)Cl] 2 ([Rh III (Cp*)(μ-Cl)Cl] 2 ) with the hydroxypyrone ligands maltol and allomaltol affords complexes of the general formula [Rh III (Cp*)(L)Cl] under standard and microwave conditions. The organometallic compounds were characterized by standard analytical methods and in the case of the allomaltol derivative in the solid state by single-crystal X-ray diffraction analysis. The complexes showed similar cytotoxicity pr...
Published on Nov 1, 2013in Talanta4.92
M.L. Mena12
Estimated H-index: 12
(Complutense University of Madrid),
Estefanía Moreno-Gordaliza11
Estimated H-index: 11
(Complutense University of Madrid),
M. Milagros Gómez-Gómez14
Estimated H-index: 14
(Complutense University of Madrid)
Abstract In this work, the reactivity of the citostatic drugs such as oxaliplatin, cisplatin and carboplatin towards proteins and the stability of Pt–protein complexes along their storage were evaluated. Neither native-PAGE nor nrSDS–PAGE seems to be suitable for the separation of carboplatin-binding proteins. A reducing electrophoretic separation procedure able to maintain the integrity of oxaliplatin–protein complexes has been developed. The method is based on SDS–PAGE under conditions provide...
Published on Jan 1, 2013in Polyhedron2.28
Hanna Pruchnik10
Estimated H-index: 10
(Wroclaw University of Environmental and Life Sciences),
Małgorzata Latocha12
Estimated H-index: 12
(Medical University of Silesia)
+ 2 AuthorsFlorian P. Pruchnik18
Estimated H-index: 18
(UWr: University of Wrocław)
Abstract Butyltin complexes with 5-sulfosalicylic acid (H 3 ssal) [Sn(C 4 H 9 ) 3 {O 3 SC 6 H 3 (OH)COOH}] ( 1 ), [Sn 2 (C 4 H 9 ) 6 (OOCC 6 H 3 OHSO 3 )] ( 2 ) and [Sn 3 (C 4 H 9 ) 6 (OOCC 6 H 3 (OH)SO 3 ) 2 O] ( 3 ) have been synthesized and characterized by ESI-MS, IR and 1 H, 13 C and 119 Sn NMR spectra. Their structures and properties in solid state and solutions were proposed on the basis of the spectroscopic data and density functional theory (DFT) calculations at B3LYP/3-21G ∗∗ level. Th...
Published on Jan 1, 2013in Chemical Communications6.16
Siming Chen6
Estimated H-index: 6
(USTC: University of Science and Technology of China),
Huan Jiang2
Estimated H-index: 2
(USTC: University of Science and Technology of China)
+ 1 AuthorsYangzhong Liu19
Estimated H-index: 19
(USTC: University of Science and Technology of China)
A widely used reducing agent tris-(2-carboxyethyl) phosphine significantly promotes the reaction of cisplatin with Sp1 zinc finger protein. This discovery clarifies the reactivity of cisplatin towards Sp1 zinc finger protein and implies that the reactions of platinum drugs could be largely influenced by small molecules with a strong trans effect.
Published on Dec 1, 2012in Inorganica Chimica Acta2.43
Yvonne Geldmacher10
Estimated H-index: 10
(RUB: Ruhr University Bochum),
Melanie Oleszak2
Estimated H-index: 2
(RUB: Ruhr University Bochum),
William S. Sheldrick42
Estimated H-index: 42
(RUB: Ruhr University Bochum)
Abstract Until recently, Rh(III) and particularly Ir(III) complexes were generally considered as being unlikely candidates for anticancer agents owing to the typical kinetic inertness of their transition metal centres. Systematic studies on the cellular impact of a range of octahedral Rh(III) complexes containing polypyridyl and other aromatic chelates have now, however, demonstrated that high cytotoxicity in cancer cells and in certain cases promising relative tolerance by healthy cells can be ...
Cited By1
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Published on Jan 1, 2017in RSC Advances3.05
Marija S. Jeremić4
Estimated H-index: 4
(University of Kragujevac),
Hubert Wadepohl34
Estimated H-index: 34
(Interdisciplinary Center for Scientific Computing)
+ 5 AuthorsPeter Comba44
Estimated H-index: 44
(Interdisciplinary Center for Scientific Computing)
Two rhodium(III) complexes [Rh(ed3a)(OH2)]·H2O (1) and Na[Rh(ed3a)Cl]·H2O (2) with ethylenediamine-N,N,N′-triacetate (ed3a) have been synthesized and characterized by elemental, spectroscopic and structural analyses. The crystal structure of (1) and (2) and the spectroscopic analysis of the two rhodium(III)–ed3a complexes are discussed in detail. The protonation constants of H3ed3a and the conditional stability constants of its RhIII complexes have been determined in aqueous solution by pH poten...
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