Anticancer Diiron Vinyliminium Complexes: A Structure-Activity Relationship Study
A series of 16 novel diiron complexes of general formula [Fe<sub>2</sub>Cp<sub>2</sub>(CO)(μ-CO){μ-η<sup>1</sup>:η<sup>3</sup>-C(R')C(R")CN(R)(Y)}]CF<sub>3</sub>SO<sub>3</sub> (<b>2-7</b>), bearing differen...
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MDPI AG,
2021-07-01T00:00:00Z.
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| LEADER | 00000 am a22000003u 4500 | ||
|---|---|---|---|
| 001 | doaj_45a5bac2851d4e8c84f26b95e8e2fd31 | ||
| 042 | |a dc | ||
| 100 | 1 | 0 | |a Simona Braccini |e author |
| 700 | 1 | 0 | |a Giorgia Rizzi |e author |
| 700 | 1 | 0 | |a Lorenzo Biancalana |e author |
| 700 | 1 | 0 | |a Alessandro Pratesi |e author |
| 700 | 1 | 0 | |a Stefano Zacchini |e author |
| 700 | 1 | 0 | |a Guido Pampaloni |e author |
| 700 | 1 | 0 | |a Federica Chiellini |e author |
| 700 | 1 | 0 | |a Fabio Marchetti |e author |
| 245 | 0 | 0 | |a Anticancer Diiron Vinyliminium Complexes: A Structure-Activity Relationship Study |
| 260 | |b MDPI AG, |c 2021-07-01T00:00:00Z. | ||
| 500 | |a 10.3390/pharmaceutics13081158 | ||
| 500 | |a 1999-4923 | ||
| 520 | |a A series of 16 novel diiron complexes of general formula [Fe<sub>2</sub>Cp<sub>2</sub>(CO)(μ-CO){μ-η<sup>1</sup>:η<sup>3</sup>-C(R')C(R")CN(R)(Y)}]CF<sub>3</sub>SO<sub>3</sub> (<b>2-7</b>), 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, <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy; moreover the X-ray structures of <b>2c</b> (R = Y = CH<sub>2</sub>Ph, R' = R" = Me) and <b>3a</b> (R = CH<sub>2</sub>CH=CH<sub>2</sub>, Y = R' = Me, R" = H) were ascertained by single-crystal X-ray diffraction studies. NMR and UV-Vis methods were used to assess the D<sub>2</sub>O 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 <b>2-7</b> against the A2780 cancer cell line, with a remarkable selectivity compared to the nontumoral Balb/3T3 cell line; complex <b>4c</b> (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). | ||
| 546 | |a EN | ||
| 690 | |a metal-based drugs | ||
| 690 | |a diiron complexes | ||
| 690 | |a cytotoxicity | ||
| 690 | |a ROS production | ||
| 690 | |a thioredoxin reductase inhibition | ||
| 690 | |a Pharmacy and materia medica | ||
| 690 | |a RS1-441 | ||
| 655 | 7 | |a article |2 local | |
| 786 | 0 | |n Pharmaceutics, Vol 13, Iss 8, p 1158 (2021) | |
| 787 | 0 | |n https://www.mdpi.com/1999-4923/13/8/1158 | |
| 787 | 0 | |n https://doaj.org/toc/1999-4923 | |
| 856 | 4 | 1 | |u https://doaj.org/article/45a5bac2851d4e8c84f26b95e8e2fd31 |z Connect to this object online. |