RT info:eu-repo/semantics/article
T1 Adding Diversity to a Diruthenium Biscyclopentadienyl Scaffold via Alkyne Incorporation: Synthesis and Biological Studies
A1 Bresciani, Giulio
A1 Boni, Serena
A1 Funaioli, Tiziana
A1 Zacchini, Stefano
A1 Pampaloni, Guido
A1 Busto Vázquez, Natalia
A1 Biver, Tarita
A1 Marchetti, Fabio
K1 Antineoplásicos
K1 Antineoplastic agents
K1 Compuestos organometálicos
K1 Organometallic compounds
AB We report the synthesis and the assessment of the anticancer potential of two series of diruthenium biscyclopentadienyl carbonyl complexes. Novel dimetallacyclopentenone compounds (2–4) were obtained (45–92% yields) from the thermal reaction (PhCCPh exchange) of [Ru2Cp2(CO)(μ-CO){μ-η1:η3-C(Ph)═C(Ph)C(═O)}], 1, with alkynes HCCR [R = C5H4FeCp (Fc), 3-C6H4(Asp), 2-naphthyl; Cp = η5-C5H5, Asp = OC(O)-2-C6H4C(O)Me]. Protonation of 1–3 by HBF4 afforded the corresponding μ-alkenyl derivatives 5–7, in 40–86% yields. All products were characterized by IR and NMR spectroscopy; moreover, cyclic voltammetry (1, 2, 5, 7) and single-crystal X-ray diffraction (5, 7) analyses were performed on representative compounds. Complexes 5–7 revealed a cytotoxic activity comparable to that of cisplatin in A549 (lung adenocarcinoma), SW480 (colon adenocarcinoma), and ovarian (A2780) cancer cell lines, and 2, 5, 6, and 7 overcame cisplatin resistance in A2780cis cells. Complexes 2, 5, and 7 (but not the aspirin derivative 6) induced an increase in intracellular ROS levels. Otherwise, 6 strongly stabilizes and elongates natural DNA (from calf thymus, CT-DNA), suggesting a possible intercalation binding mode, whereas 5 is less effective in binding CT-DNA, and 7 is ineffective. This trend is reversed concerning RNA, and in particular, 7 is able to bind poly(rA)poly(rU) showing selectivity for this nucleic acid. Complexes 5–7 can interact with the albumin protein with a thermodynamic signature dominated by hydrophobic interactions. Overall, we show that organometallic species based on the Ru2Cp2(CO)x scaffold (x = 2, 3) are active against cancer cells, with different incorporated fragments influencing the interactions with nucleic acids and the production of ROS.
PB American Chemical Society
SN 0020-1669
YR 2023
FD 2023-08
LK https://hdl.handle.net/10259/11370
UL https://hdl.handle.net/10259/11370
LA eng
NO We gratefully acknowledge for financial support La Caixa Foundation (LCF/PR/PR12/11070003), Ministerio de Ciencia, Innovación y Universidades (RTI2018-102040-B-100), Consejería de Educación, Junta de Castilla y León, FEDER (BU305P18), and the University of Pisa (Fondi di Ateneo 2021 and Fondi di Ateneo 2022). This contribution is part of the work from COST Action CA18202, NECTAR − Network for Equilibria and Chemical Thermodynamics Advanced Research, supported by COST (European Cooperation in Science and Technology). CIRCMSB (Consorzio InterUniversitario di Ricerca in Chimica dei Metalli nei Sistemi Biologici) is also acknowledged.
DS Repositorio Institucional de la Universidad de Burgos
RD 02-may-2026