Publications

Authors:

Lovison, Denise; Alessi, Dario; Allegri, Lorenzo; Baldan, Federica; Ballico, Maurizio; Damante, Giuseppe; Galasso, Marilisa; Guardavaccaro, Daniele; Melchior, Andrea; Ruggieri, Silvia; Veclani, Daniele; Nardon, Chiara; Barattaa, Walter

Title:

Enantioselective Cytotoxicity of Chiral Diphosphine Ruthenium(II) Complexes Against Cancer Cells

Year:

2022

Type of item:

Articolo in Rivista

Tipologia ANVUR:

Articolo su rivista

Language:

Inglese

Format:

A Stampa

Referee:

Sì

Name of journal:

CHEMISTRY-A EUROPEAN JOURNAL

ISSN of journal:

0947-6539

Page numbers:

1-8

Keyword:

Antitumor agents, Chirality, Cytotoxicity, N Ligands, P Ligands, Ruthenium

Short description of contents:

The chiral cationic complex [Ru(η1-OAc)(CO)((R,R)-Skewphos)(phen)]OAc (2R), isolated from [Ru(η1-OAc)(η2-OAc)(R,R)-Skewphos)(CO)] (1R) and phen, reacts with NaOPiv and KSAc affording [RuX(CO)((R,R)-Skewphos)(phen)]Y (X = Y = OPiv 3R; X = SAc, Y = OAc 4R). The corresponding enantiomers 2S-4S have been obtained from 1S containing (S,S)-Skewphos. Reaction of 2R and 2S with (S)-cysteine and NaPF6 at pH = 9 gives the diastereoisomers [Ru((S)-Cys)(CO)(PP)(phen)]PF6 (PP = (R,R)-Skewphos 2R-Cys; (S,S)-Skewphos 2S-Cys). The DFT energetic profile for 2R with (S)-cysteine in H2O indicates that aquo and hydroxo species are involved in formation of 2R-Cys. The stability of the ruthenium complexes in 0.9% NaCl solution, PBS and complete DMEM medium, as well as the n-octanol/water partition coefficient, have been evaluated. The chiral complexes show high cytotoxic activity against SW1736, 8505C, HCT-116 and A549 cell lines with EC50 values of 2.8-0.04 µM. The (R,R)-Skewphos derivatives show higher cytotoxicity compared to their enantiomers, 4R (EC50 = 0.04 µM) being 14 times more cytotoxic than 4S against the anaplastic thyroid 8505C line.

Product ID:

125553

Handle IRIS:

11562/1060797

Last Modified:

November 16, 2022

Bibliographic citation:

Lovison, Denise; Alessi, Dario; Allegri, Lorenzo; Baldan, Federica; Ballico, Maurizio; Damante, Giuseppe; Galasso, Marilisa; Guardavaccaro, Daniele; Melchior, Andrea; Ruggieri, Silvia; Veclani, Daniele; Nardon, Chiara; Barattaa, Walter, Enantioselective Cytotoxicity of Chiral Diphosphine Ruthenium(II) Complexes Against Cancer Cells «CHEMISTRY-A EUROPEAN JOURNAL» , 2022 , pp. 1-8

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