Coordination properties of the ACE inhibitor captopril towards Me 2 Sn(IV) 2+ in aqueous solution, and biological aspects of some dialkyltin(IV) derivatives of this ligand

Hajnalka Jankovics, László Nagy, Zoltán Kele, Claudio Pettinari, Paolo D'Agati, Caterina Mansueto, Claudia Pellerito, Lorenzo Pellerito

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22 Citations (Scopus)

Abstract

The coordination of Me 2 Sn(IV) 2+ (=M) to captopril {N-[(S)-3-mercapto-2-methylpropionyl]-L-proline, =H2(cap), H 2 L} in aqueous solution was studied by means of potentiometric titration, electrospray mass spectrometry, 1 H-NMR spectroscopy and Mössbauer spectroscopy in the pH range 2-11 (I=0.1 mol dm -3 NaClO 4 , 298 K). The results obtained with these methods proved that only monomeric complexes are formed in solution. In the acidic pH range, species with a metal-to-ligand ratio of 1:1 exist. The neutral complex ML, similarly to the complex Me 2 Sn(cap) crystallized in the same pH range, adopts a tbp structure with eq -S - and ax -COO - , while, instead of the coordination of the amide -C=O, observed in the solid state, the other ax position is occupied by a H 2 O molecule. With increasing pH, in the neutral and weakly basic pH range the complexes MLH -1 and ML 2 are formed, in which the -COO - group is displaced from the coordination sphere by an OH - and an S - of another ligand, respectively. Biological activity tests on Me 2 Sn(cap) and three further R 2 Sn(IV) captopril complexes showed that n-Bu 2 Sn(cap) and t-Bu 2 Sn(cap) exert toxic activity towards the embryos of Ciona intestinalis , while the ligand itself does not affect the development of the embryos to any significant extent; Me 2 Sn(cap) and Et 2 Sn(cap) produced normal swimming larvae.

Original languageEnglish
Pages (from-to)129-139
Number of pages11
JournalJournal of Organometallic Chemistry
Volume668
Issue number1-2
DOIs
Publication statusPublished - Feb 17 2003

Keywords

  • Cytotoxicity
  • Mass spectrometry
  • Mössbauer
  • NMR studies
  • Organotin compounds
  • pH-metric titration

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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