N(4)-tolyl-2-benzoylpyridine-derived thiosemicarbazones and their palladium(II) and platinum(II) complexes: Cytotoxicity against human solid tumor cells

Ferraz, Karina O.; Cardoso, Gabriele Mendes Matos; Bertollo, Caryne Margotto; Souza-Fagundes, Elaine M.; Speziali, Nivaldo L.; Zani, Carlos L.; Mendes, Isolda C.; Gomes, Maria Aparecida; Beraldo, Heloísa

doi:10.1016/j.poly.2010.10.014

Cited by 40 publications

(11 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The vibrations attributed to m(C=N) at 1554 and 1521 cm -1 in the infrared spectra of H 2 Gy3Me and H 2 Gy3Et, respectively, shift to 1574 and 1565 cm -1 in the spectra of complexes (2) and (3), in agreement with coordination of the imine nitrogen (Reis et al 2010;Ferraz et al 2011;Lessa et al 2011).…”

Section: Spectroscopic Characterizationsupporting

confidence: 54%

“…In many cases coordination to metal ions leads to improvement of the pharmacological properties of this class of compounds (Lessa et al 2011;Reis et al 2010;Ferraz et al 2011). In a previous work we demonstrated that gold(I) complexes with thiosemicarbazones were effective cytotoxic agents against human tumor cell lines and that inhibition of TrxR could be involved in their mechanism of action (Lessa et al 2011).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Spectroscopic and electrochemical characterization of gold(I) and gold(III) complexes with glyoxaldehyde bis(thiosemicarbazones): cytotoxicity against human tumor cell lines and inhibition of thioredoxin reductase activity

et al. 2012

Self Cite

View full text Add to dashboard Cite

Complexes [Au(2)(H(2)Gy3DH)(2)]Cl(2) (1), [Au(H(2)Gy3Me)]Cl(3) (2) and [Au(H(2)Gy3Et)]Cl(3) (3) were obtained with glyoxaldehyde bis(thiosemicarbazone) (H(2)Gy3DH) and its N(3)-methyl (H(2)Gy3Me) and N(3)-ethyl (H(2)Gy3Et) derivatives. The bis(thiosemicarbazones) and their gold(I) and gold(III) complexes exhibited anti-proliferative activity against HL-60, Jurkat (leukemia) and MCF-7 (breast cancer) cells at 10 μmol L(-1). Complex (2) was able to in vitro inhibit thioredoxin reductase (TrxR) activity, which suggests that inhibition of TrxR could be part of its mechanism of action.

show abstract

Section: Spectroscopic Characterizationsupporting

confidence: 54%

Section: Introductionmentioning

confidence: 99%

Spectroscopic and electrochemical characterization of gold(I) and gold(III) complexes with glyoxaldehyde bis(thiosemicarbazones): cytotoxicity against human tumor cell lines and inhibition of thioredoxin reductase activity

et al. 2012

Self Cite

View full text Add to dashboard Cite

show abstract

“…Platinum complexes are classical antitumor agents and many of them show significant cytotoxicity [50,51]. On the other hand, although several palladium compounds exhibit antiproliferative properties [52][53][54][55], none are approved for commercial distribution yet and it is important to design complexes that are potentially active against cancer. …”

Section: Resultsmentioning

confidence: 99%

“…The combination of thiosemicarbazones with platinum(II) and palladium(II) can also produce synergistic inhibition of tumor growth and may lead to improvements in the efficacy of cancer chemotherapy [4,12,13]. Palladium complexes with thiosemicarbazones show antitumor activities and some are also active in cell lines resistant to cisplatin, presenting decreased nephrotoxicity [14,15].…”

Section: Introductionmentioning

confidence: 99%

Platinum(II) and palladium(II) aryl-thiosemicarbazone complexes: synthesis, characterization, molecular modeling, cytotoxicity, and antimicrobial activity

Tavares

Paschoal

Motta

et al. 2014

Journal of Coordination Chemistry

View full text Add to dashboard Cite

Platinum(II) and palladium(II) complexes [ML 2 ] have been isolated from reaction of K 2 PtCl 4 or K 2 PdCl 4 and ligands (L) derived from thiosemicarbazones. The complexes were characterized by elemental analysis, Raman, IR, and NMR spectroscopy. In addition, quantum mechanical calculations were used to predict their structures and spectroscopic properties. For the first time, theoretical calculations using 195 Pt NMR data were used to support the suggested structures. The results indicate that the thionic sulfur and the azomethine nitrogen are bonded to the metal ion in a trans configuration. Antibacterial activities and cytotoxicities of the complexes to B16-F10 and CT26.WT cell lines were also investigated. Some of the complexes demonstrated superior cytotoxic activity compared to cisplatin.

show abstract

“…The gel was stained after electrophoresis in 0.5× TBE buffer with 2.5 μg mL –1 EB for 30 min and visualized by UV light. 40 …”

Section: Theoretical Calculationsmentioning

confidence: 99%

[Ag(L)NO₃] Complexes with 2-Benzoylpyridine-Derived Hydrazones: Cytotoxic Activity and Interaction with Biomolecules

et al. 2018

Self Cite

View full text Add to dashboard Cite

Complexes [Ag(H2BzPh)NO3] (1), [Ag(H2BzpCH3Ph)NO3] (2), [Ag(H2BzpClPh)NO3] (3), and [Ag(H2BzpNO2Ph)NO3] (4) were synthesized with 2-benzoylpyridine benzoylhydrazone (H2BzPh) and its para-methyl-benzoylhydrazone (H2BzpCH3Ph), para-chloro-benzoylhydrazone (H2BzpClPh), and para-nitro-benzoylhydrazone (H2BzpNO2Ph) derivatives. Experimental data indicate that the nitrate ligand binds more strongly to the silver center through one of the oxygen atoms, whereas the second oxygen atom from nitrate and the hydrazone oxygen makes much weaker interactions with the metal. Dissociation of nitrate most probably occurs in solution and in biological media. Interestingly, theoretical calculations suggested that when dissociation of the nitrate takes place, all bond orders involving the metal and the atoms from the hydrazone ligand increase significantly, showing that the bonding of nitrate results in the weakening of all other interactions in the metal coordination sphere. Upon complexation of the hydrazones to silver(I), cytotoxicity against B16F10 metastatic murine melanoma cells increased in all cases. Complexes (1–3) proved to be more cytotoxic than cisplatin. All compounds were more cytotoxic to B16F10 cells than to nontumorigenic murine Melan-A melanocyte cells. Interestingly, the selectivity index (SI = IC50 non-malignant cells/IC50 tumor cells) of complex (1), SI = 23, was much higher than that of the parent hydrazone ligand, SI = 9.5. Studies on the interactions of complexes (1–3) with DNA suggested that although (1–3) interact with calf thymus DNA by an intercalative mode, direct covalent binding of silver(I) to DNA probably does not occur. Complexes (1–3) interact in vitro with human serum albumin indicating that these compounds could be transported by albumin.

show abstract

N(4)-tolyl-2-benzoylpyridine-derived thiosemicarbazones and their palladium(II) and platinum(II) complexes: Cytotoxicity against human solid tumor cells

Cited by 40 publications

References 32 publications

Spectroscopic and electrochemical characterization of gold(I) and gold(III) complexes with glyoxaldehyde bis(thiosemicarbazones): cytotoxicity against human tumor cell lines and inhibition of thioredoxin reductase activity

Spectroscopic and electrochemical characterization of gold(I) and gold(III) complexes with glyoxaldehyde bis(thiosemicarbazones): cytotoxicity against human tumor cell lines and inhibition of thioredoxin reductase activity

Platinum(II) and palladium(II) aryl-thiosemicarbazone complexes: synthesis, characterization, molecular modeling, cytotoxicity, and antimicrobial activity

[Ag(L)NO₃] Complexes with 2-Benzoylpyridine-Derived Hydrazones: Cytotoxic Activity and Interaction with Biomolecules

Contact Info

Product

Resources

About

N(4)-tolyl-2-benzoylpyridine-derived thiosemicarbazones and their palladium(II) and platinum(II) complexes: Cytotoxicity against human solid tumor cells

Cited by 40 publications

References 32 publications

Spectroscopic and electrochemical characterization of gold(I) and gold(III) complexes with glyoxaldehyde bis(thiosemicarbazones): cytotoxicity against human tumor cell lines and inhibition of thioredoxin reductase activity

Spectroscopic and electrochemical characterization of gold(I) and gold(III) complexes with glyoxaldehyde bis(thiosemicarbazones): cytotoxicity against human tumor cell lines and inhibition of thioredoxin reductase activity

Platinum(II) and palladium(II) aryl-thiosemicarbazone complexes: synthesis, characterization, molecular modeling, cytotoxicity, and antimicrobial activity

[Ag(L)NO3] Complexes with 2-Benzoylpyridine-Derived Hydrazones: Cytotoxic Activity and Interaction with Biomolecules

Contact Info

Product

Resources

About

[Ag(L)NO₃] Complexes with 2-Benzoylpyridine-Derived Hydrazones: Cytotoxic Activity and Interaction with Biomolecules