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Pd(II) and Pt(II) Complexes of 2‐Phenyl‐ and 2‐Benzyl‐imidazoline: Synthesis, Structural Characterization, DNA Modification and in vitro Antileukaemic Activity
Author(s) -
Zamora Félix,
González Víctor M.,
Pérez José M.,
Masaguer José R.,
Alonso Carlos,
NavarroRanninger Carmen
Publication year - 1997
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/(sici)1099-0739(199708)11:8<659::aid-aoc614>3.0.co;2-b
Subject(s) - chemistry , circular dichroism , in vitro , dna , stereochemistry , nucleotide , covalent bond , molar ratio , medicinal chemistry , catalysis , biochemistry , organic chemistry , gene
In this paper we describe the synthesis and chemical characterization of three new Pd(II)–imidazoline complexes: [PdCl 2 (C 6 H 5 –CH 2 –C 3 H 5 N 2 ) 2 ] (2), [PdCl(SEt 2 ) (C 6 H 4 ‐C 3 H 5 N 2 )] (5) and [Pd(C 6 H 4 ‐C 3 H 5 N 2 ) (μ‐Br)] 2 (6). We have also analyzed the DNA modifications and in vitro antileukaemic activity of these compounds and of their previously reported analogs [Pd Cl 2 (C 6 H 5 –C 3 H 5 N 2 ) 2 ] (1), [Pd (C 6 H 4 –C 3 H 5 N 2 ) (μ‐OAc)] 2 (3), [Pd (C 6 H 4 –C 3 H 5 N 2 ) (μ‐Cl)] 2 (4) and [Pt(C 6 H 4 –C 3 H 5 N 2 )(μ‐Cl] (7). All these compounds modify the DNA secondary structure since they alter the melting temperature ( T m ) of the DNA. Circular dichroism spectra indicated, moreover, that compounds 3, 5 and 6 induced higher modification on the double helix than compounds 1, 2 and 4. While compounds 1, 2 and 5 seem to induce slight changes in the electrophoretic mobility of the open and covalently closed circular forms of pUC8 DNA at high r i (input molar ratio of Pd or Pt to nucleotides), compounds 3, 6 and 7 do not modify at any r i the tertiary structure of the plasmid DNA. Antileukaemic tests suggest that compounds 1, 4 and 7 exhibit important cytotoxic activity since their IC 50 values against HL‐60 human leukaemic cells were below 10 μg ml −1 . © 1997 John Wiley & Sons, Ltd.