Diorganotin(IV) N-acetyl-L-cysteinate complexes: Synthesis, solid state, solution phase, DFT and biological investigations.

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Abstract

Diorganotin(IV) complexes of N-acetyl-L-cysteine (H2NAC; (R)-2-acetamido-3-sulfanylpropanoic acid) havebeen synthesized and their solid and solution-phase structural configurations investigated by FTIR,Mössbauer, 1H, 13C and 119Sn NMR spectroscopy. FTIR results suggested that in R2Sn(IV)NAC (R=Me, Bu,Ph) complexes NAC2− behaves as dianionic tridentate ligand coordinating the tin(IV) atom, through estertypecarboxylate, acetate carbonyl oxygen atom and the deprotonated thiolate group. From 119Sn Mössbauerspectroscopy it could be inferred that the tin atom is pentacoordinated, with equatorial R2Sn(IV) trigonalbipyramidal configuration. In DMSO-d6 solution, NMR spectroscopic data showed the coordination of onesolvent molecule to tin atom, while the coordination mode of the ligand through the ester-type carboxylateand the deprotonated thiolate group was retained in solution. DFT (Density Functional Theory) studyconfirmed the proposed structures in solution phase as well as the determination of the most probable stablering conformation. Biological investigations showed that Bu2SnCl2 and NAC2 induce loss of viability in HCCcells and only moderate effects in non-tumor Chang liver cells. NAC2 showed lower cytotoxic activity thanBu2SnCl2, suggesting that the binding with NAC2− modulates the marked cytotoxic activity exerted byBu2SnCl2. Therefore, these novel butyl derivatives could represent a new class of anticancer drugs.
Lingua originaleEnglish
pagine (da-a)750-758
Numero di pagine9
RivistaJournal of Inorganic Biochemistry
Volume104
Stato di pubblicazionePublished - 2010

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Inorganic Chemistry

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