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

Abstract
Diorganotin(IV) complexes of N-acetyl-L-cysteine (H(2)NAC; (R)-2-acetamido-3-sulfanylpropanoic acid) have been synthesized and their solid and solution-phase structural configurations investigated by FTIR, Mössbauer, (1)H, (13)C and (119)Sn NMR spectroscopy. FTIR results suggested that in R(2)Sn(IV)NAC (R = Me, Bu, Ph) complexes NAC(2-) behaves as dianionic tridentate ligand coordinating the tin(IV) atom, through ester-type carboxylate, acetate carbonyl oxygen atom and the deprotonated thiolate group. From (119)Sn Mössbauer spectroscopy it could be inferred that the tin atom is pentacoordinated, with equatorial R(2)Sn(IV) trigonal bipyramidal configuration. In DMSO-d(6) solution, NMR spectroscopic data showed the coordination of one solvent molecule to tin atom, while the coordination mode of the ligand through the ester-type carboxylate and the deprotonated thiolate group was retained in solution. DFT (Density Functional Theory) study confirmed the proposed structures in solution phase as well as the determination of the most probable stable ring conformation. Biological investigations showed that Bu(2)SnCl(2) and NAC2 induce loss of viability in HCC cells and only moderate effects in non-tumor Chang liver cells. NAC2 showed lower cytotoxic activity than Bu(2)SnCl(2), suggesting that the binding with NAC(2-) modulates the marked cytotoxic activity exerted by Bu(2)SnCl(2). Therefore, these novel butyl derivatives could represent a new class of anticancer drugs.
AuthorsLorenzo Pellerito, Cristina Prinzivalli, Girolamo Casella, Tiziana Fiore, Ornella Pellerito, Michela Giuliano, Michelangelo Scopelliti, Claudia Pellerito
JournalJournal of inorganic biochemistry (J Inorg Biochem) Vol. 104 Issue 7 Pg. 750-8 (Jul 2010) ISSN: 1873-3344 [Electronic] United States
PMID20421134 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Copyright2010. Published by Elsevier Inc.
Chemical References
  • Antineoplastic Agents
  • Organotin Compounds
  • Acetylcysteine
Topics
  • Acetylcysteine (chemistry)
  • Antineoplastic Agents (chemical synthesis, chemistry)
  • Binding Sites
  • Cell Line
  • Cell Survival (drug effects)
  • Humans
  • Molecular Structure
  • Organotin Compounds (chemical synthesis, chemistry, pharmacology)
  • Spectrum Analysis

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