title: Triphenylphosphane Pt(II) complexes containing biologically active natural polyphenols: Synthesis, crystal structure, molecular modeling and cytotoxic studies.
abstract: Platinum complexes bearing phosphane ligands in cis configuration with deprotonated flavonoids (3-hydroxyflavone, quercetin) and deprotonated ethyl gallate were synthesized starting from cis-[PtCl2(PPh3)2]. In all cases, O,O' chelate structures were obtained. While quercetin and ethyl gallate complexes are quite stable in solution, the 3-hydroxyflavonate complex undergoes a slow aerobic photodegradation in solution with formation of salicylic and benzoic acids. The X-ray diffraction structures of quercetin and ethyl gallate complexes are reported. Cell cycle studies (in the dark) of the complexes in two human cell lines revealed that the cytotoxic activity of the complex bearing 3-hydroxyflavonate is higher than those exhibited by 3-hydroxyflavone or by cis-[PtCl2(PPh3)2] alone. Density functional theory studies on the hydrolysis pathway for the 3-hydroxyflavone and ethyl gallate complexes explained the different cytotoxic activity observed for the two compounds on the basis of the different intermediates formed during hydrolysis (relatively inert hydroxy Pt complexes for ethyl gallate and monoaqua complexes for 3-hydroxyflavone).
authors: DICATECh, Politecnico di Bari, via Orabona, 4, I-70125 Bari, Italy. Electronic address: mariamichela.dellanna@poliba.it.
authors: Maria Michela
authors: MM
authors: Dell'Anna
authors: DICATECh, Politecnico di Bari, via Orabona, 4, I-70125 Bari, Italy.
authors: Valentina
authors: V
authors: Censi
authors: Institute of Crystallography CNR, via Amendola, 122/o, I-70126 Bari, Italy.
authors: Benedetta
authors: B
authors: Carrozzini
authors: Institute of Crystallography CNR, via Amendola, 122/o, I-70126 Bari, Italy.
authors: Rocco
authors: R
authors: Caliandro
authors: Department of Pharmacy, University of Bari, via Orabona, 4, I-70125 Bari, Italy.
authors: Nunzio
authors: N
authors: Denora
authors: Department of Pharmacy, University of Bari, via Orabona, 4, I-70125 Bari, Italy.
authors: Massimo
authors: M
authors: Franco
authors: Dipartimento Politecnico di Ingegneria e Architettura, Laboratori di Tecnologie Chimiche, University of Udine, via del Cotonificio 108, I-33100 Udine, Italy.
authors: Daniele
authors: D
authors: Veclani
authors: Dipartimento Politecnico di Ingegneria e Architettura, Laboratori di Tecnologie Chimiche, University of Udine, via del Cotonificio 108, I-33100 Udine, Italy.
authors: Andrea
authors: A
authors: Melchior
authors: Dipartimento Politecnico di Ingegneria e Architettura, Laboratori di Tecnologie Chimiche, University of Udine, via del Cotonificio 108, I-33100 Udine, Italy.
authors: Marilena
authors: M
authors: Tolazzi
authors: DICATECh, Politecnico di Bari, via Orabona, 4, I-70125 Bari, Italy.
authors: Piero
authors: P
authors: Mastrorilli
mesh_terms: D018360:Crystallography, X-Ray; D003603:Cytotoxins / Q000138:chemical synthesis / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology; D006801:Humans; D061986:MCF-7 Cells; D008958:Models, Molecular; D009944:Organoplatinum Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology; D059808:Polyphenols / Q000138:chemical synthesis / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology
chemical_list: D003603:Cytotoxins; D009944:Organoplatinum Compounds; D059808:Polyphenols
keywords: Cytotoxic activity; DFT; Flavonoids; Natural polyphenols; Platinum(II) complexes