Zinc(II) Complexes of Acylpyrazolones Decorated with a Cyclohexyl Group Display Antiproliferative Activity Against Human Breast Cancer Cells

Marchetti, Fábio; Nicola, Corrado Di; Pettinari, Riccardo; Pettinari, Cláudio; Aiello, Iolinda; Deda, Massimo La; Candreva, Angela; Morelli, Sabrina; Bartolo, Loredana De; Crispini, Alessandra

doi:10.1002/ejic.201900775

Cited by 15 publications

(14 citation statements)

References 59 publications

(122 reference statements)

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“…The beneficial effect of incorporating the cyclohexyl moiety (Cy) within anticancer metal compounds was previously recognized and attributed to its compact and hydrophobic structure. 65 − 67 …”

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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“…The bond lengths of Zn1–N1, Zn1–O1, Zn1–O2, Zn1–O3B, Zn1–O5, and Zn1–O6 are 2.109(3), 2.445(2), 2.058(3), 2.018(3), 2.085(3) and 2.098(3) Å, respectively, which are similar to those of other Zn‐based complexes. [ 25 ] The bond length of Zn1–O2 is longer than those of the other ones. Thus, the oxygen atom (O2) is considered to coordinate very weakly to the Zn1 atom but is a non‐negligible interaction.…”

Section: Resultsmentioning

confidence: 99%

Metal ions Directed Self‐assembly based on Mixed Ligands: From 2D hcb Net to 3D cds Framework

Zhang

Sun

et al. 2020

Zeitschrift anorg allge chemie

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Two coordination polymers (CPs), namely, [Zn(BPDC)(3bpdb) 0.5 (H 2 O) 2 ] n (1), and [Ni(BPDC)(3-bpdb)(H 2 O) 2 ] n (2) (where H 2 BPDC = 4,4'-biphenyldicarboxylic acid, 3-bpdb = 1,4-bis(3-pyridyl)-2,3-diaza-1,3-butadiene) have been solvothermally synthesized and characterized by single-crystal X-ray diffraction, IR, elemental analyses, PXRD, and SEM. CP 1 possesses a 2D 3-connected hcb net, and weak hydrogen bonding and π•••π stacking contacts further link the 2D networks to form 3D supramolecular structure. The structure

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Zinc(II) Complexes of Acylpyrazolones Decorated with a Cyclohexyl Group Display Antiproliferative Activity Against Human Breast Cancer Cells

Cited by 15 publications

References 59 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

Metal ions Directed Self‐assembly based on Mixed Ligands: From 2D hcb Net to 3D cds Framework

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