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 slowaerobic photodegradation in solutionwith 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).

Triphenylphosphane Pt(II) complexes containing biologically active natural polyphenols: Synthesis, crystal structure, molecular modeling and cytotoxic studies / Dell'Anna, Maria Michela; Censi, Valentina; Carrozzini, Benedetta; Caliandro, Rocco; Denora, Nunzio; Franco, Massimo; Veclani, Daniele; Melchior, Andrea; Tolazzi, Marilena; Mastrorilli, Pietro. - In: JOURNAL OF INORGANIC BIOCHEMISTRY. - ISSN 0162-0134. - STAMPA. - 163:(2016), pp. 346-361. [10.1016/j.jinorgbio.2016.08.006]

Triphenylphosphane Pt(II) complexes containing biologically active natural polyphenols: Synthesis, crystal structure, molecular modeling and cytotoxic studies

DELL'ANNA, Maria Michela
;
CENSI, Valentina;CALIANDRO, Rocco;MASTRORILLI, Pietro
2016-01-01

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 slowaerobic photodegradation in solutionwith 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).
2016
Triphenylphosphane Pt(II) complexes containing biologically active natural polyphenols: Synthesis, crystal structure, molecular modeling and cytotoxic studies / Dell'Anna, Maria Michela; Censi, Valentina; Carrozzini, Benedetta; Caliandro, Rocco; Denora, Nunzio; Franco, Massimo; Veclani, Daniele; Melchior, Andrea; Tolazzi, Marilena; Mastrorilli, Pietro. - In: JOURNAL OF INORGANIC BIOCHEMISTRY. - ISSN 0162-0134. - STAMPA. - 163:(2016), pp. 346-361. [10.1016/j.jinorgbio.2016.08.006]
File in questo prodotto:
File Dimensione Formato  
JINORGBIO-S-16-00150 submitted.pdf

accesso aperto

Descrizione: manuscript pre-referaggio
Tipologia: Documento in Pre-print
Licenza: Creative commons
Dimensione 1.77 MB
Formato Adobe PDF
1.77 MB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11589/79999
Citazioni
  • Scopus 23
  • ???jsp.display-item.citation.isi??? 22
social impact