Heterometallic platinum(<scp>ii</scp>) compounds with β-aminoethylferrocenes: synthesis, electrochemical behaviour and anticancer activity

Nieto, Daniel; González-Vadillo, Ana Ma; Bruña, Sonia; Pastor, César J.; Rios‐Luci, Carla; León, Leticia G.; Padrón, José M.; Navarro‐Ranninger, Carmen; Cuadrado, Isabel

doi:10.1039/c1dt11358e

Cited by 46 publications

(40 citation statements)

References 74 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The anticancer properties of certain molecules may be increased by the introduction of the organometallic ferrocene motif in the framework due to its low toxicity, high lipophilicity and unique electrochemical behavior. 27–29 Thus, several examples of heterometallic complexes incorporating ferrocene and a second cytotoxic metal (Au(I), 30–36 Pt(II), 30,37–42 Pd(II), 40,43–45 Ru(II), 46–50 Rh(I) 40,51,52 Ir(I), 40 and Cu(I) 53,54 ) appeared in the literature. In most cases the antiproliferative properties of the resulting compounds improved with respect of that of the corresponding ferrocene-based ligand, although synergistic effects of the effects of the two different metals were evaluated only in one case.…”

Section: Introductionmentioning

confidence: 99%

Potential Anticancer Heterometallic Fe–Au and Fe–Pd Agents: Initial Mechanistic Insights

et al. 2013

View full text Add to dashboard Cite

A series of gold(III) and palladium(II) heterometallic complexes with new iminophosphorane ligands derived from ferrocenyl-phosphanes [{Cp-P(Ph2)=N-Ph}2Fe] (1), [{Cp-P(Ph2)=N-CH2-2-NC5H4}2Fe] (2) and [{Cp-P(Ph2)=N-CH2-2-NC5H4}Fe(Cp)] (3) have been synthesized and structurally characterized. Ligands 2 and 3 afford stable coordination complexes [AuCl2(3)]ClO4, [{AuCl2}2(2)](ClO4)2, [PdCl2(3)] and [{PdCl2}2(2)]. The complexes have been evaluated for their antripoliferative properties in human ovarian cancer cells sensitive and resistant to cisplatin (A2780S/R), in human breast cancer cells (MCF7) and in a non-tumorigenic human embryonic kidney cell line (HEK-293T). The highly cytotoxic trimetallic derivatives M2Fe (M = Au, Pd) are more cytotoxic to cancer cells than their corresponding monometallic fragments. Moreover, these complexes were significantly more cytotoxic than cisplatin in the resistant A2780R and the MCF7 cell lines. Studies of the interactions of the trimetallic compounds with DNA and the zinc-finger protein PARP-1 indicate that they exert anticancer effects in vitro based on different mechanisms of actions with respect to cisplatin.

show abstract

Section: Introductionmentioning

confidence: 99%

Potential Anticancer Heterometallic Fe–Au and Fe–Pd Agents: Initial Mechanistic Insights

et al. 2013

View full text Add to dashboard Cite

show abstract

“…Complex 17 was completely inactive, but 18 was more potent than cisplatin against the resistant WiDr colon cancer cell line. Flow cytometry studies of 18 revealed that the trinuclear complex did not induce cell cycle arrest, but the cell cycle distribution was significantly different to that of cisplatin, thereby suggesting a different mode of action …”

Section: Platinummentioning

confidence: 98%

“…Cuadrado and colleagues investigated the combination of ferrocene and platinum by coordinating β‐aminoethylferrocenyl ligands to cisplatin fragments. This resulted in a cationic binuclear complex ( 17 ), a trinuclear complex ( 18 ) and a neutral binuclear complex ( 19 ).…”

Section: Platinummentioning

confidence: 99%

See 1 more Smart Citation

Heterometallic Multinuclear Complexes as Anti‐Cancer Agents‐An Overview of Recent Developments

2019

View full text Add to dashboard Cite

This review provides a critical assessment of the advances made in the development of heterometallic multinuclear complexes as potential chemotherapeutic agents, with the aim of providing a starting point for future investigators. The combination of the classical transition metals (Pt, Ru and Au) with other metal moieties has the potential to result in complexes with improved pharmacokinetic and pharmacodynamic properties. This enables selective targeting of the bio- [a] 3434 Figure 2. The Pt II -Ru III complexes, IT127 and AH-197, [35] and the macrocyclic rectangles investigated by Chi and colleagues. [36] The IC 50 (μM) values reported are shown below the chemical structures.

show abstract

“…[4] Besides platinum-based metallodrugs, transitionmetal-based complexes, such as ferrocene-bearing compounds, have shown strong antiproliferative effects in vitro as well as antitumor effects in vivo. [9,[11][12][13] Some of these compounds have shown promising IC 50 values ( Figure 3): (i) Nieto et al recently published the successful synthesis and first cell culture tests of a cis-configured ferrocene-platinum derivative, which showed in vitro activity in human breast, cervix, lung and colon cancer cells in the low micromolar range (partially exceeding the antiproliferative activity of cisplatin); [11] (ii) a trans-dichloridoplatinum(II) complex featuring two ferrocene-bound phosphane units was designed by Schulz et al, which yielded low IC 50 values in the micromolar range in the ovarian cancer cell line A2780. In 1996, Jaouen et al coupled ferrocene to 4-hydroxytamoxifen and modified the length of the carbon chain in order to optimize its pharmacological properties ( Figure 2).…”

Section: Introductionmentioning

confidence: 99%

Platinum(IV) Complexes Featuring One or Two Axial Ferrocene Bearing Ligands – Synthesis, Characterization, and Cytotoxicity

et al. 2013

View full text Add to dashboard Cite

Ferrocenyl compounds show interesting antiproliferative properties. Consequently, ferrocene bearing moieties were prepared and coupled for the first time to anticancer platinum(IV) complexes. The compounds, featuring either one or two axially coordinated ferrocene-containing ligands, were fully characterized by ESI-MS and multinuclear ( 1 H, 13 C, 15 N, and 195 Pt) one-and two-dimensional NMR spectroscopy. 484Their cytotoxicity was investigated in three human cancer cell lines deriving from ovarian carcinoma (CH1), colon carcinoma (SW480), and non-small-cell lung carcinoma (A549) by means of the colorimetric MTT assay. Promising IC 50 values in the low micromolar range in CH1 and SW480 human cancer cells were found. www.eurjic.org FULL PAPER Scheme 1. Synthesis of ferrocene precursors L2-L6 and NMR numbering scheme. Scheme 2. Synthesis of complexes 3-5 and NMR numbering scheme. 486 www.eurjic.org FULL PAPER Scheme 3. Synthesis of platinum(IV) complexes 11-15 and NMR numbering scheme.As described in the literature, [16] novel Pt IV complexes with the Cl 2 N 2 O 2 coordination sphere show 195 Pt resonances in the region around 2656 ppm, whereas resonances for oxaliplatin-type platinum(IV) complexes appear in the region of 3230 ppm. As anticipated, the 195 Pt resonances are comparable for oxaliplatin-based Pt IV complexes 13, 14, and 15 with one acetato and one derivatized carboxylato ligand in the axial position to those for their biscarboxylated analogues. ESI-MS spectra were measured in the positive as well as in the negative mode. The highest peak observed in each spectrum in the positive mode is [M + Na] + , which is also in accordance with the calculated values.

show abstract

Heterometallic platinum(ii) compounds with β-aminoethylferrocenes: synthesis, electrochemical behaviour and anticancer activity

Cited by 46 publications

References 74 publications

Potential Anticancer Heterometallic Fe–Au and Fe–Pd Agents: Initial Mechanistic Insights

Potential Anticancer Heterometallic Fe–Au and Fe–Pd Agents: Initial Mechanistic Insights

Heterometallic Multinuclear Complexes as Anti‐Cancer Agents‐An Overview of Recent Developments

Platinum(IV) Complexes Featuring One or Two Axial Ferrocene Bearing Ligands – Synthesis, Characterization, and Cytotoxicity

Contact Info

Product

Resources

About