Match!

Palladium(II) complexes with tris(2-carboxyethyl)phosphine, structure, reactions and cytostatic activity

Published on Mar 1, 2016in Journal of Inorganic Biochemistry3.224
· DOI :10.1016/j.jinorgbio.2015.12.001
Hanna Pruchnik11
Estimated H-index: 11
(Wroclaw University of Environmental and Life Sciences),
Tadeusz Lis31
Estimated H-index: 31
(UWr: University of Wrocław)
+ 2 AuthorsFlorian P. Pruchnik19
Estimated H-index: 19
(UWr: University of Wrocław)
Abstract
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 2 ( μ -Cl) 2 Cl 2 (TCEP) 2 ] ( 2 ) were fully characterized by 1 H, 13 C, 31 P NMR, IR and ESI-MS spectroscopic techniques. Complexes are stable in non-aqueous DMSO and DMF. In aqueous solutions Cl ligands are substituted by COO groups of phosphines. Complex 2 , after crystallization from water gives polymeric compound with bridging phosphine ligand [PdCl{P(RCOO- κO - μ - O ′)(RCOOH) 2 - κP }] ( 3 ). Structures of trans -[PdCl 2 {P(RCOOD) 3 } 2 ] ( 1a ), trans -[Pd 2 ( μ -Cl) 2 PdCl 2 {P(RCOOD) 3 } 2 ] ( 2a ), and [PdCl{P(RCOO -κO - μ - O ′)(RCOOD) 2 - κP }] n ( 3a ) have been determined by X-ray crystallography. NMR and ESI-MS spectra reveal that [PdP 2 (RCOO- κO ) 2 (RCOO) n (RCOOH) 4 − n ] n – complexes are formed in aqueous solution of 1 . Geometry optimization in the gas phase at the B3LYP/3-21G** level indicated that complex 2 with butterfly structure is more stable than that with coplanar coordination. In aqueous solution of 2 , the main products [Pd 2 {P(RCOO -κO - μ - O ′)(RCOO- κO )(RCOOH)} 2 ] and [Pd{P(RCOO- κO ) 2 (RCOOH)}(H 2 O)] exist in equilibrium which depends on temperature: content of mononuclear compound increases as the temperature is raised. Complexes 1 and 2 are active agents against melanoma and breast cancer cells.
  • References (36)
  • Citations (6)
📖 Papers frequently viewed together
9 Citations
7 Citations
21 Citations
78% of Scinapse members use related papers. After signing in, all features are FREE.
References36
Newest
#1Hanna Pruchnik (Wroclaw University of Environmental and Life Sciences)H-Index: 11
#2Tadeusz Lis (UWr: University of Wrocław)H-Index: 31
Last. Florian P. Pruchnik (UWr: University of Wrocław)H-Index: 19
view all 3 authors...
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...
9 CitationsSource
#1Samantha M. McNeill (University of Otago)H-Index: 2
#2Dan Preston (University of Otago)H-Index: 10
Last. James D. Crowley (University of Otago)H-Index: 36
view all 9 authors...
There is emerging interest in the anti-proliferative effects of metallosupramolecular systems due to the different size and shape of these metallo-architectures compared to traditional small molecule drugs. Palladium(II)-containing systems are the most abundant class of metallosupramolecular complexes, yet their biological activity has hardly been examined. Here a small series of [Pd2(L)4](BF4)4 quadruply-stranded, dipalladium(II) architectures were screened for their cytotoxic effects against t...
45 CitationsSource
Currently, organic crystal structure prediction (CSP) methods are based on searching for the most thermodynamically stable crystal structure, making various approximations in evaluating the crystal energy. The most stable (global minimum) structure provides a prediction of an experimental crystal structure. However, depending on the specific molecule, there may be other structures which are very close in energy. In this case, the other structures on the crystal energy landscape may be polymorphs...
239 CitationsSource
#1William M. Motswainyana (UWC: University of the Western Cape)H-Index: 7
#2Martin O. Onani (UWC: University of the Western Cape)H-Index: 9
Last. Roger A. Lalancette (RU: Rutgers University)H-Index: 28
view all 6 authors...
Abstract The imino-phosphine ligands L1 and L2 were prepared via condensation reaction of 2-(diphenylphosphino)benzaldehyde with substituted anilines and obtained in very good yields. An equimolar reaction of L1 and L2 with either PdCl2(cod) or PtCl2(cod) gave new palladium(II) and platinum(II) complexes 1–4. The compounds were characterized by elemental analysis, IR, 1H and 31P NMR spectroscopy. The molecular structures of 2, 3 and 4 were confirmed by X-ray crystallography. All the three molecu...
19 CitationsSource
#1M.L. Mena (Complutense University of Madrid)H-Index: 12
#2Estefanía Moreno-Gordaliza (Complutense University of Madrid)H-Index: 12
Last. M. Milagros Gómez-Gómez (Complutense University of Madrid)H-Index: 16
view all 3 authors...
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...
11 CitationsSource
#1Natalia Cutillas (University of Murcia)H-Index: 15
#2Gorakh S. Yellol (University of Murcia)H-Index: 9
Last. José Ruiz (University of Murcia)H-Index: 30
view all 6 authors...
Abstract The clinical success of cisplatin and its derivatives has had an enormous impact on the discovery of novel metal-based drugs. Extensive studies have focused on the interaction of metal complexes with their potential targets. The array of organometallic compounds with useful anticancer activity has been significantly extended with respect to metals and structures. This review highlights recent exciting results in the field of cyclometalated C N complexes and C N C, C N N and C N S pincer...
166 CitationsSource
#1Kazem Karami (IUT: Isfahan University of Technology)H-Index: 17
#2Mahboubeh Hosseini Kharat (IUT: Isfahan University of Technology)H-Index: 2
Last. Mina Mirian (IUMS: Isfahan University of Medical Sciences)H-Index: 7
view all 5 authors...
Abstract Reaction of chloro-bridged dinuclear palladacycles, [Pd2{(C,N)-C6H4CH2NH(R)}2(μ-Cl)2] (R = Et (1a); R = t-Bu (1b)) with pyridine and PPh3 in the 1:2 M ratio at room temperature was used to prepare the mononuclear complexes, [Pd(C,N)-C6H4CH2NH(R)Cl(L)] (R = Et and L = Py (2a); R = t-Bu and L = PPh3 (2b)). Bridged biphosphinic palladacycle, [Pd2(C,N-dmba)2(μ-dppe)(Cl)2] (2c), (where dmba = N,N-dimethylbenzylamine and dppe = 1,2-bis(diphenylphosphino)ethane) has been also synthesized. The ...
25 CitationsSource
#1Siming Chen (USTC: University of Science and Technology of China)H-Index: 6
#2Huan Jiang (USTC: University of Science and Technology of China)H-Index: 2
Last. Yangzhong Liu (USTC: University of Science and Technology of China)H-Index: 20
view all 4 authors...
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.
17 CitationsSource
#1Hanna Pruchnik (Wroclaw University of Environmental and Life Sciences)H-Index: 11
#2Małgorzata Latocha (Medical University of Silesia)H-Index: 11
Last. Florian P. Pruchnik (UWr: University of Wrocław)H-Index: 19
view all 5 authors...
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...
10 CitationsSource
#1Hanna Pruchnik (Wroclaw University of Environmental and Life Sciences)H-Index: 11
#2Tadeusz Lis (UWr: University of Wrocław)H-Index: 31
Last. Florian P. Pruchnik (UWr: University of Wrocław)H-Index: 19
view all 7 authors...
Abstract Three butyltin complexes with 2-sulfobenzoic acid [Sn(C 4 H 9 ) 2 {O 3 SC 6 H 4 COO-2}(H 2 O)]·(C 2 H 5 OH) ( 1 ), [Sn(C 4 H 9 ) 3 {O 3 SC 6 H 4 COOH-2}] ( 2 ) and [Sn 2 (C 4 H 9 ) 6 {μ-O 3 SC 6 H 4 COO-2}] ( 3 ) have been synthesized and characterized by IR and 1 H, 13 C and 119 Sn NMR spectra. They show interesting properties in solid state and solutions because there are many modes of coordination of the Sbz ligand. The structure of complex 1 has been determined by X-ray crystallogra...
18 CitationsSource
Cited By6
Newest
#1Banafshe AskariH-Index: 5
#2Hadi Amiri RudbariH-Index: 22
view all 7 authors...
Source
#1Martin Vojtek (University of Porto)H-Index: 1
#2Maria Paula M. Marques (UC: University of Coimbra)H-Index: 23
Last. Carmen Diniz (University of Porto)H-Index: 12
view all 5 authors...
Treatment of triple-negative breast carcinoma (TNBC) remains an unmet medical need with no targeted therapy available to date. Accounting for 10–30% of all human breast cancer tumors, this mammary carcinoma subtype has a particularly poor prognosis owing to its high metastatic potential, aggressive biology and limited pharmacological treatment options. Platinum chemotherapeutics are the mainstay therapy in patients with TNBC but their clinical use is limited by severe toxicity and acquired resis...
3 CitationsSource
#1Philippa K. Coffer (Durham University)H-Index: 3
#2Keith B. Dillon (Durham University)H-Index: 16
Last. Helena J. Shepherd (Durham University)H-Index: 20
view all 5 authors...
The coordination properties of the 2-aryl-1,3,2-dioxaphospholane 2,6-(CF3)2C6H3P(OCH2)21 (L) have been investigated, by reaction with elemental selenium in solution to form the phosphorus(V) oxidation product 2,6-(CF3)2C6H3P(Se)(OCH2)22, and with metal-containing precursors to form three new complexes trans-[PdCl(μ-Cl)(L)]23, cis-[PdMe2L2] 4 and [AuCl(L)] 5. All of the metal complexes have been characterised by single-crystal X-ray structure determination.
Source
#1Sourav Bhowmick (IITP: Indian Institute of Technology Patna)H-Index: 7
#2Achintya Jana (IITP: Indian Institute of Technology Patna)H-Index: 5
Last. Neeladri Das (IITP: Indian Institute of Technology Patna)H-Index: 17
view all 7 authors...
A facile and efficient synthesis of a series of five new pyrazine-based organometallic complexes is being reported. The complexes (2–6) have been fully characterized. Molecules 2, 3 and 6 were structurally characterized by single crystal X-ray crystallographic analyses. Additionally, anticancer properties of these organometallic complexes have been studied against A549 human lung carcinoma cells. Biological studies suggest that complex 5 (with pendant pyridine moieties) exhibited maximal growth ...
4 CitationsSource
#1Mohamed Gaber (Tanta University)H-Index: 21
#2Hoda A. El-Ghamry (Tanta University)H-Index: 10
Last. Mohammed A. Mansour (Tanta University)H-Index: 9
view all 3 authors...
Pd (II) and Pt(II) complexes of (E)-3-(4-(dimethylamino)phenyl)-1-(pyridin-2-yl) prop-2-en-1-one (L) and its Pd (II) and Pt(II) formulated as [Pt(L1)2] Cl2. 2H2O, [Pd (L1)2] Cl2 0.5H2O, [Pd (L1)2] (AcO)2 CH3OH have been synthesized. Elemental analyses, molar conductance, thermal technique, molecular modeling, IR and electronic spectral measurements were used to verify the structures of the complexes. The titled ligand behaves as a neutral bidentate ligand coordination via pyridine nitrogen and c...
4 CitationsSource
#1Hanna Pruchnik (Wroclaw University of Environmental and Life Sciences)H-Index: 11
#2Małgorzata Latocha (Medical University of Silesia)H-Index: 11
Last. Florian P. Pruchnik (UWr: University of Wrocław)H-Index: 19
view all 4 authors...
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 ...
1 CitationsSource
#1Yan Zheng (SDU: Shandong University)H-Index: 6
#2Liying Fang (SDU: Shandong University)H-Index: 1
Last. Yanzhao Yang (SDU: Shandong University)H-Index: 13
view all 6 authors...
Abstract The silicone ionic liquid, 1-methyl-3-[tri-(trimethylsiloxy)]silylpropyl-imidazolium chloride ([Si 4 mim]Cl), was first used for the construction of the W/O microemulsion system and the [Si 4 mim]Cl/ n -heptane/ n -hexanol/NaCl microemulsion system was applied for palladium extraction for the first time. The stability of [Si 4 mim]Cl/ n -heptane/ n -hexanol/NaCl microemulsion system was characterized by the Turbiscan Lab. For the Pd (II) extraction by the [Si 4 mim]Cl/ n -heptane/ n -he...
8 CitationsSource