Synthesis, characterization and antiproliferative studies of the enantiomers of cis-[(1,2-camphordiamine)dichloro]platinum(II) complexes

Ángel M. Montaña, Francisco J. Bernal, Julia Lorenzo, Carlos Farnós, Consuelo Batalla, Maria J. Prieto, Virtudes Moreno, Francesc X. Avilés, Juan M. Mesas, María Teresa Alegre

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35 Citations (Scopus)

Abstract

The platinum(II) complex cis-[(1S,2R,3S)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-diamine]dichloroplatinum(II) (1) and its enantiomer (2) have been synthesized and physically and spectroscopically characterized. To obtain the enantiopure complexes the chiral pool approach was applied. The synthetic pathway has four steps, starting from (±)-diphenylethylenediamine (DPEDA) (3) and the natural products (1S)-camphorquinone or (1R)-camphorquinone to obtain enantiomers 1 and 2, respectively. The interaction of the Pt(II) complexes with DNA was studied by several techniques: circular dichroism, electrophoresis on agarose gel and atomic force microscopy (AFM). These studies showed differences in the degree of interaction between both enantiomers and DNA (calf thymus DNA and plasmid pBR322 DNA). The cytotoxicity of enantiomers 1 and 2 against the HL-60 cell line was studied by in vitro tests of antiproliferative activity, incubating during both 24 h and 72 h. An important difference of activity was found between both enantiomers regarding the IC50 data at 24 h of incubation. Thus, complex 1 showed to be much more active than its enantiomer 2. © 2007 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)1721-1737
JournalBioorganic and Medicinal Chemistry
Volume16
DOIs
Publication statusPublished - 15 Feb 2008

Keywords

  • 1,2-Camphordiamines
  • Anticancer agents
  • Apoptosis
  • Atomic force microscopy
  • Circular dichroism
  • Cytotoxicity
  • DNA
  • Enantiomers
  • Platinum(II) complexes

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