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Spectroscopic studies of amino acid ionic liquid-supported Schiff bases.

ABSTRACT: Amino acid ionic liquid-supported Schiff bases, derivatives of salicylaldehyde and various amino acids (L-threonine, L-valine, L-leucine, L-isoleucine and L-histidine) have been investigated by means of various spectroscopic techniques (NMR, UV-Vis, IR, MS) and deuterium isotope effects on ¹³C-NMR chemical shifts. The results have shown that in all studied amino acid ionic liquid-supported Schiff bases (except the L-histidine derivative) a proton transfer equilibrium exists and the presence of the COO? group stabilizes the proton transferred NH-form.

SUBMITTER: Ossowicz P

PROVIDER: S-EPMC6269710 | biostudies-literature | 2013 Apr

REPOSITORIES: biostudies-literature

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Spectroscopic studies of amino acid ionic liquid-supported Schiff bases.

Ossowicz Paula P Janus Ewa E Schroeder Grzegorz G Rozwadowski Zbigniew Z

Molecules (Basel, Switzerland) 20130429 5

Amino acid ionic liquid-supported Schiff bases, derivatives of salicylaldehyde and various amino acids (L-threonine, L-valine, L-leucine, L-isoleucine and L-histidine) have been investigated by means of various spectroscopic techniques (NMR, UV-Vis, IR, MS) and deuterium isotope effects on ¹³C-NMR chemical shifts. The results have shown that in all studied amino acid ionic liquid-supported Schiff bases (except the L-histidine derivative) a proton transfer equilibrium exists and the presence of t ...[more]

PMID: 23629755

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Project description:In this contribution, five Ni(II) complexes have been synthesized from sulfonamide-based Schiff bases (SB1-SB5) that comprise bromo or iodo substituents in the salicylidene moiety. The chemical structures of these compounds were extensively elucidated by different analytical and physicochemical studies. All ligands act as bidentate chelators with ON binding mode yielding octahedral, square planar, or tetrahedral geometries. The phenolic OH at δ 12.80 ppm in the free Schiff base SB2 vanishes in the 1H NMRspectrum of diamagnetic complex [Ni(SB2-H)2] favoring the OH deprotonation prior to the chelation with Ni(II) ion. The appearance of twin molecular ion peaks ([M - 1]+ and [M + 1]+) is due to the presence of bromine isotopes (79Br and 81Br) in the mass spectra of most cases. Also, the thermal decomposition stages of all complexes confirmed their high thermal stability and ended with the formation of NiO residue of mass 6.42% to 14.18%. Besides, antimicrobial activity and cytotoxicity of the ligands and some selected complexes were evaluated. Among the ligands, SB4 showed superior antimicrobial efficacy with MIC values of 0.46, 7.54, and 0.95 µM against B. subtilis, E. coli, and A. fumigatus strains, respectively. The consortium of different substituents as two bromine atoms either at positions 3 and/or 5 on the phenyl ring and a thiazole ring is one of the reasons behind the recorded optimal activity. Moreover, there is a good correlation between the cytotoxicity screening (IC50) and molecular docking simulation outcomes that predicted a strong binding of SB2 (16.0 μM), SB4 (18.8 μM), and SB5 (6.32 μM) to the breast cancer protein (3s7s). Additionally, [Ni(SB4-H)2] (4.33 µM) has nearly fourfold potency in comparison with cisplatin (19.0 μM) against breast carcinoma cells (MCF-7) and is highly recommended as a promising, potent, as well as low-cost non-platinum antiproliferative agent after further drug authorization processes.

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Spectroscopic studies of amino acid ionic liquid-supported Schiff bases.

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Spectroscopic studies of amino acid ionic liquid-supported Schiff bases.

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