Cytotoxic palladium(II) complexes of 8-aminoquinoline derivatives and the interaction with human serum albumin

Yan, Liangliang; Wang, Xiaoyong; Wang, Yanqing; Zhang, Yangmiao; Li, Yi‐Zhi; Guo, Zijian

doi:10.1016/j.jinorgbio.2011.09.032

Cited by 55 publications

(19 citation statements)

References 41 publications

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“…Attempts to correlate the Ka of a drug with the percentage plasma protein binding have been carried out [59, 60]. The first binding constant for the Pt compound ( 4 ) (1.43 ± 0.13)×10 4 is correlated with a roughly 90% plasma protein binding which is considered the upper limit for effective chemotherapeutics (values higher than 90% are considered to be disadvantageous).…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic hydrophilic iminophosphorane coordination compounds of d8 metals. Studies of their interactions with DNA and HSA

Carreira

Calvo-Sanjuán

Sanaú

et al. 2012

Journal of Inorganic Biochemistry

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The synthesis and characterization of a new water-soluble N,N-chelating iminophosphorane ligand TPA=N-C(O)-2-NC5H4 (N,N-IM) (1) and its d8 (AuIII, PdII and PtII) coordination complexes are reported. The structures of cationic [AuCl2(N,N-IM)] ClO4 (2) and neutral [MCl2(N,N-IM)] M = Pd (3), Pt(4) complexes were determined by X-ray diffraction studies or by means of density-functional calculations. While the Pd and Pt compounds are stable in mixtures of DMSO/H2O over 4 days, the gold derivative (2) decomposes quickly to TPA=O and previously reported neutral gold(III) compound [AuCl2(N,N-H)] 5 (containing the chelating N,N- fragment HN-C(O)-2-NC5H4). The cytotoxicities of complexes 2–5 were evaluated in vitro against human Jurkat-T acute lymphoblastic leukemia cells and DU-145 human prostate cancer cells. Pt (4) and Au compounds (2 and 5) are more cytotoxic than cisplatin to these cell lines and to cisplatin-resistant Jurkat sh-Bak cell lines and their cell death mechanism is different from that of cisplatin. All the compounds show higher toxicity against leukemia cells when compared to normal human T-lymphocytes (PBMC). The interaction of the Pd and Pt compounds with calf thymus and plasmid (pBR322) DNA is different from that of cisplatin. All compounds bind to human serum albumin (HSA) faster than cisplatin (measured by fluorescence spectroscopy). Weak and stronger binding interactions were found for the Pd (3) and Pt (4) derivatives by isothermal titration calorimetry. Importantly, for the Pt (4) compounds the binding to HSA was reversed by addition of a chelating agent (citric acid) and by a decrease in pH.

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Section: Resultsmentioning

confidence: 99%

Cytotoxic hydrophilic iminophosphorane coordination compounds of d8 metals. Studies of their interactions with DNA and HSA

Carreira

Calvo-Sanjuán

Sanaú

et al. 2012

Journal of Inorganic Biochemistry

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“…Palladium(II) complexes present alternative candidates for antitumor metallo-based drugs due to their structural and thermodynamic resemblances to the platinum(II) complexes which have been widely used in the treatment of various malignancies. Compared to extensively used carboplatin, it is shown that palladium(II) complexes containing coumarins as ligands, where the environment of the palladium atom is similar to that of carboplatin, display 7800 times higher cytotoxicity [ 17 , 18 ]. Also, compared to platinum(II) complexes, palladium(II) complexes have better solubility and aquation and ligand-exchange rates about 10 4 –10 5 times greater [ 18 , 19 ].…”

Section: Introductionmentioning

confidence: 99%

“…Compared to extensively used carboplatin, it is shown that palladium(II) complexes containing coumarins as ligands, where the environment of the palladium atom is similar to that of carboplatin, display 7800 times higher cytotoxicity [ 17 , 18 ]. Also, compared to platinum(II) complexes, palladium(II) complexes have better solubility and aquation and ligand-exchange rates about 10 4 –10 5 times greater [ 18 , 19 ]. Regarding presented advantages, there is growing interest in the synthesis and examination of biological effects of palladium(II)-coumarin-based complexes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Screening of New 4‐Hydroxycoumarin Derivatives and Their Palladium(II) Complexes

Avdović

Petrović

Stevanović

et al. 2021

Oxidative Medicine and Cellular Longevity

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Two newly synthesized 4-hydroxycoumarin bidentate ligands (L1 and L2) and their palladium(II) complexes (C1 and C2) were screened for their biological activities, in vitro and in vivo. Structures of new compounds were established based on elemental analysis, 1H NMR, 13C NMR, and IR spectroscopic techniques. The obtained compounds were tested for their antioxidative and cytotoxic activities and results pointed to selective antiradical activity of palladium(II) complexes towards •OH and -•OOH radicals and anti-ABTS (2,2 ′ -Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) cation radical) activity comparable to that of ascorbate. Results indicated the effect of C1 and C2 on the enzymatic activity of the antioxidative defense system. In vitro cytotoxicity assay performed on different carcinoma cell lines (HCT166, A375, and MIA PaCa-2), and one healthy fibroblast cell line (MRC-5) showed a cytotoxic effect of both C1 and C2, expressed as a decrease in carcinoma cells’ viability, mostly by induction of apoptosis. In vivo toxicity tests performed on zebrafish embryos indicated different effects of C1 and C2, ranging from adverse developmental effect to no toxicity, depending on tested concentration. According to docking studies, both complexes (C1 and C2) showed better inhibitory activity in comparison to other palladium(II) complexes.

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“…Serum albumin (SA) is a multiple function protein and acts as the transporter and disposition of many endogenous and exogenous ligands, including fatty acids, amino acids, metals ions, and numerous pharmaceuticals by means of hydrogen bonding, hydrophobic, electrostatic, and metal interactions [4][5][6][7]. e interaction intensity between antitumor drugs and SA may effect on their bioavailability and toxicity [8][9][10]. In this regard, bovine serum albumin (BSA) has been studied extensively, partly because of its structural homology with human serum albumin (HSA).…”

Section: Introductionmentioning

confidence: 99%

Fluorescence Spectroscopy Study on the Interaction between Evodiamine and Bovine Serum Albumin

Tan

Liang

Luo

et al. 2012

Journal of Chemistry

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The interaction of evodiamine (Evo) with bovine serum albumins (BSAs) at different two temperatures (298 and 310 K) was investigated by means of fluorescence spectroscopy. The experimental results showed that Evo binds with BSA via a static quenching procedure with association constantsKof1.61×106 L/mol at 298 K and6.78×105 L/mol at 310 K. The number of bound Evo molecules per protein is 1.31 at 298 K and 1.33 at 310 K. The results suggested that Evo reacts with BSA chiefly through hydrophobic and electrostatic interactions, and it does not alter theα-helical nature of BAS.

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Cytotoxic palladium(II) complexes of 8-aminoquinoline derivatives and the interaction with human serum albumin

Cited by 55 publications

References 41 publications

Cytotoxic hydrophilic iminophosphorane coordination compounds of d8 metals. Studies of their interactions with DNA and HSA

Cytotoxic hydrophilic iminophosphorane coordination compounds of d8 metals. Studies of their interactions with DNA and HSA

Synthesis and Biological Screening of New 4‐Hydroxycoumarin Derivatives and Their Palladium(II) Complexes

Fluorescence Spectroscopy Study on the Interaction between Evodiamine and Bovine Serum Albumin

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