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Complexes of Pd(II) and Pt(II) with 9-aminoacridine: reactions with DNA and study of their antiproliferative activity.

Riera X, Moreno V, Ciudad CJ, Noe V, Font-Bardía M, Solans X - Bioinorg Chem Appl (2007)

Bottom Line: Both palladium and platinum compounds proved active in the modification of both the secondary and tertiary DNA structures.AFM images showed noticeable modifications of the morphology of the plasmid pBR322 DNA by the compounds probably due to the intercalation of the complexes between base pairs of the DNA molecule.The results suggest that the palladium complex of formula [Pd(9AA)(mu-Cl)](2) has significant antiproliferative activity, although it is less active than cisplatin.

View Article: PubMed Central - PubMed

Affiliation: Departamento de Química Inorgànica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain. xavier.riera-palou@shell.com

ABSTRACT
Four new metal complexes {M = Pd(II) or Pt(II)} containing the ligand 9-aminoacridine (9AA) were prepared. The compounds were characterized by FT-IR and (1)H, (13)C, and (195)Pt NMR spectroscopies. Crystal structure of the palladium complex of formulae [Pd(9AA)(mu-Cl)](2) . 2DMF was determined by X-ray diffraction. Two 9-acridine molecules in the imine form bind symmetrically to the metal ions in a bidentate fashion through the imine nitrogen atom and the C(1) atom of the aminoacridine closing a new five-membered ring. By reaction with phosphine or pyridine, the Cl bridges broke and compounds with general formulae [Pd(9AA)Cl(L)] (where L = PPh(3) or py) were formed. A mononuclear complex of platinum of formulae [Pt(9AA)Cl(DMSO)] was also obtained by direct reaction of 9-aminoacridine and the complex [PtCl(2)(DMSO(2)]. The capacity of the compounds to modify the secondary and tertiary structures of DNA was evaluated by means of circular dichroism and electrophoretic mobility. Both palladium and platinum compounds proved active in the modification of both the secondary and tertiary DNA structures. AFM images showed noticeable modifications of the morphology of the plasmid pBR322 DNA by the compounds probably due to the intercalation of the complexes between base pairs of the DNA molecule. Finally, the palladium complex was tested for antiproliferative activity against three different human tumor cell lines. The results suggest that the palladium complex of formula [Pd(9AA)(mu-Cl)](2) has significant antiproliferative activity, although it is less active than cisplatin.

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1H NMRspectrum (zone 6–11.5ppm) of the complex [Pd(9AA)Cl(PPh3)]. *Signalassigned to the DMF present in the precursor complex [Pd(9AA)(μ-Cl2)] ⋅ 2DMF.
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fig1: 1H NMRspectrum (zone 6–11.5ppm) of the complex [Pd(9AA)Cl(PPh3)]. *Signalassigned to the DMF present in the precursor complex [Pd(9AA)(μ-Cl2)] ⋅ 2DMF.

Mentions: A noticeable feature in the spectrum of [Pd(9AA)-Cl(PPh3)] (see Figure 1) is that the signal of the iminic proton (NH9) appears as a doublet due to the couplingwith the 31P (3JP-H9 = 5 Hz) nucleous. For the same reason, the H2 resonance appears as a doublet of doublets (4JP-H2 = 5 Hz). The values of these coupling constants are similar to those of analogue compounds described in the literature [48].


Complexes of Pd(II) and Pt(II) with 9-aminoacridine: reactions with DNA and study of their antiproliferative activity.

Riera X, Moreno V, Ciudad CJ, Noe V, Font-Bardía M, Solans X - Bioinorg Chem Appl (2007)

1H NMRspectrum (zone 6–11.5ppm) of the complex [Pd(9AA)Cl(PPh3)]. *Signalassigned to the DMF present in the precursor complex [Pd(9AA)(μ-Cl2)] ⋅ 2DMF.
© Copyright Policy - open-access
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC2266976&req=5

fig1: 1H NMRspectrum (zone 6–11.5ppm) of the complex [Pd(9AA)Cl(PPh3)]. *Signalassigned to the DMF present in the precursor complex [Pd(9AA)(μ-Cl2)] ⋅ 2DMF.
Mentions: A noticeable feature in the spectrum of [Pd(9AA)-Cl(PPh3)] (see Figure 1) is that the signal of the iminic proton (NH9) appears as a doublet due to the couplingwith the 31P (3JP-H9 = 5 Hz) nucleous. For the same reason, the H2 resonance appears as a doublet of doublets (4JP-H2 = 5 Hz). The values of these coupling constants are similar to those of analogue compounds described in the literature [48].

Bottom Line: Both palladium and platinum compounds proved active in the modification of both the secondary and tertiary DNA structures.AFM images showed noticeable modifications of the morphology of the plasmid pBR322 DNA by the compounds probably due to the intercalation of the complexes between base pairs of the DNA molecule.The results suggest that the palladium complex of formula [Pd(9AA)(mu-Cl)](2) has significant antiproliferative activity, although it is less active than cisplatin.

View Article: PubMed Central - PubMed

Affiliation: Departamento de Química Inorgànica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain. xavier.riera-palou@shell.com

ABSTRACT
Four new metal complexes {M = Pd(II) or Pt(II)} containing the ligand 9-aminoacridine (9AA) were prepared. The compounds were characterized by FT-IR and (1)H, (13)C, and (195)Pt NMR spectroscopies. Crystal structure of the palladium complex of formulae [Pd(9AA)(mu-Cl)](2) . 2DMF was determined by X-ray diffraction. Two 9-acridine molecules in the imine form bind symmetrically to the metal ions in a bidentate fashion through the imine nitrogen atom and the C(1) atom of the aminoacridine closing a new five-membered ring. By reaction with phosphine or pyridine, the Cl bridges broke and compounds with general formulae [Pd(9AA)Cl(L)] (where L = PPh(3) or py) were formed. A mononuclear complex of platinum of formulae [Pt(9AA)Cl(DMSO)] was also obtained by direct reaction of 9-aminoacridine and the complex [PtCl(2)(DMSO(2)]. The capacity of the compounds to modify the secondary and tertiary structures of DNA was evaluated by means of circular dichroism and electrophoretic mobility. Both palladium and platinum compounds proved active in the modification of both the secondary and tertiary DNA structures. AFM images showed noticeable modifications of the morphology of the plasmid pBR322 DNA by the compounds probably due to the intercalation of the complexes between base pairs of the DNA molecule. Finally, the palladium complex was tested for antiproliferative activity against three different human tumor cell lines. The results suggest that the palladium complex of formula [Pd(9AA)(mu-Cl)](2) has significant antiproliferative activity, although it is less active than cisplatin.

No MeSH data available.


Related in: MedlinePlus