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

Pellerito, Lorenzo; Prinzivalli, Cristina; Casella, Girolamo; Fiore, Tiziana; Pellerito, Ornella; Giuliano, Michela; Scopelliti, Michelangelo; Pellerito, Claudia

doi:10.1016/j.jinorgbio.2010.03.008

Cited by 20 publications

(6 citation statements)

References 65 publications

(69 reference statements)

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“…In the 119 Sn{ 1 H} spectra, caf1 shows a single sharp resonance at −129 ppm, value pointing to a pentacoordinated tin, where the fifth coordination is attained by the presence of the coordinated solvent DMSOd 6 molecule in the tin coordination sphere [32][33][34].…”

Section: Nmr Solution Spectramentioning

confidence: 99%

Synthesis, chemical characterization, computational studies and biological activity of new DNA methyltransferases (DNMTs) specific inhibitor. Epigenetic regulation as a new and potential approach to cancer therapy

Pellerito

Morana

Ferrante

et al. 2015

Journal of Inorganic Biochemistry

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Section: Nmr Solution Spectramentioning

confidence: 99%

Synthesis, chemical characterization, computational studies and biological activity of new DNA methyltransferases (DNMTs) specific inhibitor. Epigenetic regulation as a new and potential approach to cancer therapy

Pellerito

Morana

Ferrante

et al. 2015

Journal of Inorganic Biochemistry

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“…N -Acetylcysteine rarely acts as a bidentate ( S,O )-donor chelating ligand to form a 6-membered metallocycle with the metal ion. , More often it is monodentate, binding only through its thiolate group to metal ions such as Cr(VI), Bi(III), , or bridging between two metal ions like Pt(II) in a dimeric complex, as evidenced by X-ray crystallography or X-ray absorption spectroscopy. Recent reports based on 13 C NMR and FT-IR spectroscopic techniques have suggested that Pt(II), Au(I), and Ag(I) ions bind exclusively to the S atom in their N -acetylcysteine complexes, − while bidentate and even tridentate coordination modes have been proposed for Zn II ( S,O -NAC) and R 2 Sn IV (NAC) complexes, respectively.…”

Section: Introductionmentioning

confidence: 99%

Similarities between N-Acetylcysteine and Glutathione in Binding to Lead(II) Ions

Sisombath

Jalilehvand

2015

Chem. Res. Toxicol.

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N -acetylcysteine is a natural thiol-containing antioxidant, a precursor for cysteine and glutathione, and a potential detoxifying agent for heavy metal ions. However, previous accounts of the efficiency of N-acetylcysteine (H2NAC) in excretion of lead are few and contradicting. Here we report results on the nature of lead(II) complexes formed with N-acetylcysteine in aqueous solution, which were obtained by combining information from several spectroscopic methods, including 207Pb, 13C and 1H NMR, Pb LIII-edge X-ray absorption, Ultraviolet-visible (UV-vis.) spectroscopy and electro-spray ionization mass spectrometry (ESI-MS). Two series of solutions were used containing CPb(II) = 10 and 100 mM, respectively, varying the H2NAC / Pb(II) mole ratios from 2.1 to 10.0 at pH = 9.1 – 9.4. The coordination environments obtained resemble those previously found for the Pb(II) glutathione system: at a ligand-to-lead mole ratio of 2.1 dimeric or oligomeric Pb(II) N-acetylcysteine complexes are formed, while a tri-thiolate [Pb(NAC)3]4− complex dominates in solutions with H2NAC/Pb(II) mole ratios > 3.0.

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“…It is indicated that these types of functionals can provide better results compared to local spin density approximation or generalized gradient approximations in thermo-chemistry or structural calculations [12]. Density functional theory and hybrid methods are successfully applied in organotin chemistry covering studies such as chemical reactivity description [13], calculating nonlinear optical properties [14][15][16], obtaining 119 Sn isotropic shielding and coupling constants [17][18][19], investigating Mössbauer quadrupole splitting behaviors [20,21], and other structure interpretation studies [22][23][24]. However, organotin(IV) complexes derived from Schiff bases are of interest due to their various important biological properties [25][26][27], synthetic chemistry applications [28,29], and nonlinear optical properties [14][15][16][17], yet theoretical studies concerning complexes derived from ONO-donor type Schiff base ligands are very limited in the literature.…”

Section: Introductionmentioning

confidence: 99%

Theoretical studies of organotin(IV) complexes derived from ONO-donor type schiff base ligands

2015

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In this work a molecular modeling study was carried out based on a series of organotin(IV) derivatives which were complexed with ONO-Donor type Schiff base ligands to build up a statistical data pool for researchers. For this purpose, various properties of the selected complexes such as energies, band gaps, chemical reactivity descriptors, polarizabilities, geometric parameters, (1)H-NMR, (13)C-NMR chemical shifting values were obtained through density functional theory using B3LYP, CAM-B3LYP, TPSSTPSS, TPSSh, HCTH, wB97XD, and MN12SX functionals. Empirical dispersion corrections were incorporated for some functionals and solvent effects were also taken into account through applying polarizable continuum model (PCM). (1)H-NMR, (13)C-NMR chemical shifts were calculated via linear regression analysis using either gauge invariant atomic orbital (GIAO) or continuous set of gauge transformations (CSGT) methods. While structural properties were being explored, quantitative effects of utilized functionals and empirical dispersion corrections over calculated properties were shown in detail.

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

Cited by 20 publications

References 65 publications

Synthesis, chemical characterization, computational studies and biological activity of new DNA methyltransferases (DNMTs) specific inhibitor. Epigenetic regulation as a new and potential approach to cancer therapy

Synthesis, chemical characterization, computational studies and biological activity of new DNA methyltransferases (DNMTs) specific inhibitor. Epigenetic regulation as a new and potential approach to cancer therapy

Similarities between N-Acetylcysteine and Glutathione in Binding to Lead(II) Ions

Theoretical studies of organotin(IV) complexes derived from ONO-donor type schiff base ligands

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