Syntheses, Structures, and Biological Activity of NiII, PdII, and PtII Complexes with New Tetradentate Benzamidine Ligands

Nguyen, Thi Bao Yen; Nguyen, Minh Le; Abram, Ulrich; Nguyen, Hung Huy

doi:10.1002/zaac.201500203

Cited by 2 publications

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“…As can be seen from Table , the proligand H 2 L was devoid of any activity within the whole concentration range tested, and all complexes were more cytotoxic than H 2 L alone, indicating the role of metal centers in their moderate biological effects. Similar trends have been previously observed in the literature. , We speculate that fine-tuning of the N , N ′-bis(2-aminoethyl)oxamide scaffold might result in a marked increase in the cytotoxicity of its metal complexes.…”

Section: Resultssupporting

confidence: 90%

“…Similar trends have been previously observed in the literature. 27,30 We speculate that fine-tuning of the N,N′-bis(2-aminoethyl)oxamide scaffold might result in a marked increase in the cytotoxicity of its metal complexes.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…In fact, the structurally similar to cisplatin palladium complex cis -Pd(NH 3 ) 2 Cl 2 , which was among the first palladium(II) anticancer agents tested, demonstrated low anticancer activity because of hydrolytic instability and thereby inability to reach its pharmacological targets. Therefore, kinetically more inert palladium(II) complexes with strongly coordinated polychelate nitrogen ligands have been subsequently developed. , These complexes could maintain their structural integrity in cells and demonstrated high antiproliferative activity, − sometimes higher than that of their platinum congeners. In particular, it was shown that square-planar palladium(II) complexes with malamido- N,N′- diacetic acid and oxamido- N,N′- di-3-propionic acid revealed very high antiproliferative activity and lower resistance of tumor cells in vitro in comparison to cisplatin .…”

Section: Introductionmentioning

confidence: 99%

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Palladium Complexes of N,N′-Bis(2-aminoethyl)oxamide (H₂L): Structural (Pd^IIL, Pd^II₂L₂, and Pd^IVLCl₂), Electrochemical, Dynamic ¹H NMR, and Cytotoxicity Studies

et al. 2018

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The monomeric (PdL·2HO) and dimeric (PdL·7HO) palladium(II) complexes of N,N'-bis(2-aminoethyl)oxamide (HL) were isolated, and their structures were established by single-crystal X-ray diffraction. Both compounds display identical cis-(2N + 2N) coordination environments of the metal ion. The dimer, representing a combination of two PdL species with an open lateral chelate ring, has an "open clamshell"-like structure. The intramolecular metal-metal separation in PdL (3.215 Å) is slightly shorter than the sum of the van der Waals radii of the palladium(II) atoms. The dimeric complex is relatively stable to dissociation, and its spectral features in aqueous solutions have been compared to those of the monomeric complex. A H NMR spectroscopic study revealed the presence of the dynamic conformational exchange process assigned to a turning of the dimeric molecule "inside out" with an activation energy of 65 kJ/mol. Cyclic voltammetry of PdL in perchlorate-, chloride-, and sulfate-containing electrolytes revealed two-electron oxidation of the palladium center. For the dimeric complex similar, though irreversible, oxidation to the palladium(IV) state was observed in NaCl electrolyte. At the same time, in NaClO or NaSO solutions oxidation of PdL occurs in two distinct steps. The first step is quasi-reversible and can be assigned to the formation of species in an intermediate PdPd state. Monomeric palladium(IV) complex PdLCl was generated via chemical oxidation of PdL by peroxodisulfate in the presence of chloride ions and structurally characterized. The related ML complexes (M = Pd, Ni, Cu) showed low cytotoxicity in human cancer cell lines AGS (gastric adenocarcinoma) and HCT116 (colorectal carcinoma) with IC values from 204 to 525 μM, while the proligand HL was devoid of antiproliferative activity (IC > 1000 μM).

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Section: Resultssupporting

confidence: 90%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Palladium Complexes of N,N′-Bis(2-aminoethyl)oxamide (H₂L): Structural (Pd^IIL, Pd^II₂L₂, and Pd^IVLCl₂), Electrochemical, Dynamic ¹H NMR, and Cytotoxicity Studies

et al. 2018

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Synthesis, Structures, and Properties of Four Novel Coordination Compounds based on a Flexible Tetrakis(imidazol‐1‐ylmethyl)methane Ligand

Wang

et al. 2016

Zeitschrift anorg allge chemie

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Four coordination polymers, namely, [Zn 2 (TIYM)(2,6-PYDC) 2 ] n ·n(CH 3 OH)·3n(H 2 O) (1), [Cu(TIYM)(2,6-PYDC)] n ·3n(H 2 O) (2), [Co(TIYM)(2,6-PYDC)] n ·n(CH 3 OH)·3n(H 2 O) (3), and [Cd 2 (TIYM)(2,6-PYDC) 2 (H 2 O)] n ·n(H 2 O) (4) with the flexible N-containing ligand [tetrakis(imidazol-1-ylmethyl)methane (TIYM)] and the N-containing dicarboxylic acid [2,6-pyridinedicarboxylic acid (2,6-PYDC)] were prepared. Compounds 1-4 show various structures because of different N-C center -N angles (θ) of TIYM ligands and chang-* Prof. Dr. L. Du

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Syntheses, Structures, and Biological Activity of Ni^II, Pd^II, and Pt^II Complexes with New Tetradentate Benzamidine Ligands

Abstract: Abstract. N-(Dialkylthiocarbamoyl (6)]. In all complexes, H 2 L R is doubly deprotonated and bonded to the metal ion via its N 2 OS donor set and establishes a distorted

Cited by 2 publications

References 17 publications

Palladium Complexes of N,N′-Bis(2-aminoethyl)oxamide (H₂L): Structural (Pd^IIL, Pd^II₂L₂, and Pd^IVLCl₂), Electrochemical, Dynamic ¹H NMR, and Cytotoxicity Studies

Palladium Complexes of N,N′-Bis(2-aminoethyl)oxamide (H₂L): Structural (Pd^IIL, Pd^II₂L₂, and Pd^IVLCl₂), Electrochemical, Dynamic ¹H NMR, and Cytotoxicity Studies

Synthesis, Structures, and Properties of Four Novel Coordination Compounds based on a Flexible Tetrakis(imidazol‐1‐ylmethyl)methane Ligand

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Syntheses, Structures, and Biological Activity of NiII, PdII, and PtII Complexes with New Tetradentate Benzamidine Ligands

Abstract: Abstract. N-(Dialkylthiocarbamoyl (6)]. In all complexes, H 2 L R is doubly deprotonated and bonded to the metal ion via its N 2 OS donor set and establishes a distorted

Cited by 2 publications

References 17 publications

Palladium Complexes of N,N′-Bis(2-aminoethyl)oxamide (H2L): Structural (PdIIL, PdII2L2, and PdIVLCl2), Electrochemical, Dynamic 1H NMR, and Cytotoxicity Studies

Palladium Complexes of N,N′-Bis(2-aminoethyl)oxamide (H2L): Structural (PdIIL, PdII2L2, and PdIVLCl2), Electrochemical, Dynamic 1H NMR, and Cytotoxicity Studies

Synthesis, Structures, and Properties of Four Novel Coordination Compounds based on a Flexible Tetrakis(imidazol‐1‐ylmethyl)methane Ligand

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Syntheses, Structures, and Biological Activity of Ni^II, Pd^II, and Pt^II Complexes with New Tetradentate Benzamidine Ligands

Palladium Complexes of N,N′-Bis(2-aminoethyl)oxamide (H₂L): Structural (Pd^IIL, Pd^II₂L₂, and Pd^IVLCl₂), Electrochemical, Dynamic ¹H NMR, and Cytotoxicity Studies

Palladium Complexes of N,N′-Bis(2-aminoethyl)oxamide (H₂L): Structural (Pd^IIL, Pd^II₂L₂, and Pd^IVLCl₂), Electrochemical, Dynamic ¹H NMR, and Cytotoxicity Studies