Synthesis of newN,N′-Pd(Pt) complexes based on sulfanyl pyrazoles, and investigation of theirin vitroanticancer activity

Ахметова, В. Р.; Абдуллин, М. И.; Dzhemileva, Lilya U.; D’yakonov, Vladimir A.

doi:10.1039/c9ra09783j

Cited by 18 publications

(11 citation statements)

References 35 publications

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“…In addition to 1 and 7 , complex 8 (log P ow = 0.34), bearing a cyclohexyl isocyanide ligand, also showed very good activity, still roughly comparable to cisplatin. The beneficial effect of incorporating the cyclohexyl moiety (Cy) within anticancer metal compounds was previously recognized and attributed to its compact and hydrophobic structure. − …”

Section: Resultsmentioning

confidence: 99%

Ruthenium(II)–Tris-pyrazolylmethane Complexes Inhibit Cancer Cell Growth by Disrupting Mitochondrial Calcium Homeostasis

et al. 2022

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While ruthenium arene complexes have been widely investigated for their medicinal potential, studies on homologous compounds containing a tridentate tris(1-pyrazolyl)methane ligand are almost absent in the literature. Ruthenium(II) complex 1 was obtained by a modified reported procedure; then, the reactions with a series of organic molecules (L) in boiling alcohol afforded novel complexes 2 – 9 in 77–99% yields. Products 2–9 were fully structurally characterized. They are appreciably soluble in water, where they undergo partial chloride/water exchange. The antiproliferative activity was determined using a panel of human cancer cell lines and a noncancerous one, evidencing promising potency of 1 , 7 , and 8 and significant selectivity toward cancer cells. The tested compounds effectively accumulate in cancer cells, and mitochondria represent a significant target of biological action. Most notably, data provide convincing evidence that the mechanism of biological action is mediated by the inhibiting of mitochondrial calcium intake.

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Section: Resultsmentioning

confidence: 99%

Ruthenium(II)–Tris-pyrazolylmethane Complexes Inhibit Cancer Cell Growth by Disrupting Mitochondrial Calcium Homeostasis

et al. 2022

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“…Complex 4c , derived from the assembly of cyclohexylisocyanide and 2-butyne ( Table 2 ), appears as the most performant within the series of vinyliminium complexes 2–7 . The favorable effect on the anticancer activity provided by the decoration of metal complexes with the cyclohexyl (Cy) moiety has been documented in the literature, attributed to the compact and hydrophobic structure of Cy facilitating the entrance of the drug into the tumor cell [ 72 , 73 , 74 ].…”

Section: Resultsmentioning

confidence: 99%

Anticancer Diiron Vinyliminium Complexes: A Structure–Activity Relationship Study

et al. 2021

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A series of 16 novel diiron complexes of general formula [Fe2Cp2(CO)(μ-CO){μ-η1:η3-C(R′)C(R″)CN(R)(Y)}]CF3SO3 (2–7), bearing different substituents on the bridging vinyliminium ligand, was synthesized in 69–95% yields from the reactions of diiron μ-aminocarbyne precursors with various alkynes. The products were characterized by elemental analysis, IR, 1H and 13C NMR spectroscopy; moreover the X-ray structures of 2c (R = Y = CH2Ph, R′ = R″ = Me) and 3a (R = CH2CH=CH2, Y = R′ = Me, R″ = H) were ascertained by single-crystal X-ray diffraction studies. NMR and UV–Vis methods were used to assess the D2O solubility, the stability in aqueous solution at 37 °C and the octanol–water partition coefficients of the complexes. A screening study evidenced a potent cytotoxicity of 2–7 against the A2780 cancer cell line, with a remarkable selectivity compared to the nontumoral Balb/3T3 cell line; complex 4c (R = Cy, Y = R′ = R″ = Me) revealed as the most performant of the series. The antiproliferative activity of a selection of complexes was also assessed on the cisplatin-resistant A2780cisR cancer cell line, and these complexes were capable of inducing a significant ROS production. Moreover, ESI-MS experiments indicated the absence of interaction of selected complexes with cytochrome c and the potentiality to inhibit the thioredoxin reductase enzyme (TrxR).

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“…Note that the bond lengths in the 3,5‐dimethylpyrazole moieties of 7a, 7d , and 7f are similar and are in line with the data we obtained previously. [ 17,18 ] Indeed, the N1–N2 bond lengths in 7a, 7d , and 7f differ little, amounting to 1.360, 1.355, and 1.352 Å, respectively. The С8–S1 bond is longer than S1–C15, being 1.8506(17), 1.860(2), and 1.842(3) Å in 7a, 7d , and 7f , respectively.…”

Section: Resultsmentioning

confidence: 99%

“…[17,18] Indeed, the N1-N2 bond lengths in 7a, 7d, and 7f differ little, amounting to 1.360, 1.355, and 1.352 Å, respectively. The С8-S1 bond is longer than S1-C15, being 1.8506 (17), 1.860(2), and 1.842(3) Å in 7a, 7d, and 7f, respectively. The C-S bond is elongated compared with that in 4-(sulfanylmethyl)-3,5-dimethyl-1H-pyrazole derivatives that we obtained previously if an aromatic substituent is attached to this moiety, [17] rather than an aliphatic substituent.…”

Section: S C H E M E 4 Diversification Of Hydroxysulfanylazole Scaffoldsmentioning

confidence: 99%

DOS strategy, crystal structure, and in silico evaluation of the anti‐inflammatory activity of hydroxysulfanylazole derivatives

Akhmadiev

Mescheryakova

Khayrullina

et al. 2022

J Chinese Chemical Soc

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We developed a DOS approach to the synthesis of hydroxysulfanylazole derivatives (12 examples) using diversification with various N,N-and N,Obinucleophilic reagents of the carbonyl groups of hydroxysulfanyl diketones (6 examples) obtained by the piperidine-catalyzed thiomethylation reaction involving the С(α)-Н position of 2,4-pentanedione with aromatic aldehydes and 2-mercaptoethanol. X-ray diffraction analysis was used to determine the structures and crystal packing for three hydroxysulfanylpyrazoles. The calculation of the intermolecular interactions in the crystals (analysis of Hirshfeld surfaces) demonstrated the influence of the substituent nature on the contribution of the H…O/O…H contacts. Using molecular docking studies, justified assumptions were made about the complementarity of the obtained series of compounds to the active sites of COX isoforms.

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Synthesis of newN,N′-Pd(Pt) complexes based on sulfanyl pyrazoles, and investigation of theirin vitroanticancer activity

Abstract: Efficient cytostatics against Jurkat, K562 and U937 neoplastic cell lines were found among the synthesized new Pd(ii) and Pt(ii)complexes (six examples) with sulfanyl-1H-pyrazole ligands using in vitro assay.

Cited by 18 publications

References 35 publications

Ruthenium(II)–Tris-pyrazolylmethane Complexes Inhibit Cancer Cell Growth by Disrupting Mitochondrial Calcium Homeostasis

Ruthenium(II)–Tris-pyrazolylmethane Complexes Inhibit Cancer Cell Growth by Disrupting Mitochondrial Calcium Homeostasis

Anticancer Diiron Vinyliminium Complexes: A Structure–Activity Relationship Study

DOS strategy, crystal structure, and in silico evaluation of the anti‐inflammatory activity of hydroxysulfanylazole derivatives

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