Synthesis and DFT Study of the Complexation of Schiff Base Derived Curcumin and L-Tyrosine with Al(III), Ag(I), and Pb(II) Metal Ions

Abstract

The multi-dentate Schiff base ligand (H2L), where H2L=2,2'-(((1,3,5,6)-1-(3-((l1-oxidaneyl)-l5-methyl)-4-hydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-diylidene)bis(azaneylylidene))bis(3-(4-hydroxyphenyl)propanoic acid), has been prepared from curcumin and L- Tyrosine amino acid. The synthesized Schiff base ligand (H2L) and the second ligand 1,10-phenanthroline (phen) are used to prepare the new complexes [Al(L)(phen)]Cl, K[Ag(L)(phen)] and [Pb(L)(phen)]. The synthesized compounds are characterized by magnetic susceptibility measurements, micro elemental analysis (C.H.N), mass spectrometry, molar conductance, FT-infrared, UV-visible, atomic absorption (AA), 13C-NMR, and 1H-NMR spectral studies. The characterization of the synthesized complexes shows that the environment surrounding the central metal ion in the complexes adopted a distorted octahedral configuration. Moreover, the conductivity measurements show a non-electrolytic character for the [Pb(L)(phen)] complex and an electrolytic character for the [Al(L)(phen)]Cl and K[Ag(L)(phen)] complexes. The experimental infrared data are supported by density functional theory (DFT) calculations using the B3LYP level of theory and LANL2DZ basis set. The vibrational frequencies of the molecules are computed using the optimized geometry obtained from the DFT calculations. The calculated vibrational frequencies have been compared with obtained experimental values. 1H and 13C-NMR chemical shifts were computed for the H2L ligand using the DFT/GIAO method. Additionally, the molecular electronic structures of the complexes have been investigated by DFT calculations.

Preparation, Structural Characterization and Biological Activities of Curcumin-Metal(II)-L-3,4-dihydroxyphenylalanin (L-dopa) complexes

“…Generally, the complexes were prepared by reacting the respective metal salts with the ligands using [Cur:M: (L-dopa)2] mole ratio, i.e. one mole of curcumin , one mole of metal salt and two mole of (Ldopa) [9] as the following equations:…”

“…The Curcumin complexes of the Schiff Base [ (Curc )-L-Tyrosine] with Pb(II) , Al(III), and Ag(I) Ions constitute an especially interesting series of compounds. [9]. Complexation of curcumin with transition metals were synthesized, characterized and evaluated for various biological activities [10].…”

Nuclear Magnetic Resonance

“…56 Complexation of Schiff base derived curcumin and L-tyrosine with Al(III), Ag(I), and Pb(II) diamagnetic metal ions was studied experimentally and GIAO calculations supported the analysis of the observed NMR spectra. 57 Synthesis and experimental characteristics, supported by GIAO NMR calculations, on several novel pyrrole-3-ones 58 and 2-(piperidin-1-ylmethyl)-isoindoline-1,3-dione 59 were reported. An interesting study on mechanochemical synthesis of the catechol-theophylline cocrystal was reported.…”

A Short Review: Chemistry of Curcumin and Its Metal Complex Derivatives

“…Zn(II)-curcumin [37] Cu (II)--curcumin [38] , [39] Cr(III)--curcumin [40] Mixed ligand Schiff base with 1,10-phnanothroline, M= Co or Cu [41] Pd(II)-curcumin [42] M(diacetylcurcumin) 2 , where M= Cu(II) and Ni(II) [43] Ln=Eu(III) &La(III), rare earth -curcumin [44] M-curcumin, M=Cr(III),Mn(II), Fe(III), Co(II), Ni(II), Cu(II) ,Zn(II) [45] Mixed metal (Fe (II) &Cu(II)) -curcumin [46] Complexes of Curcuminoid-BF 2 [47] In acidic condition, Rosocyanine is produced as 2:1-complex from curcumin and boric acid [48] Curcumin-Fe(III) [49] Drug containing Rh(III) and curcumin (*Cp) ,*pentamethylcyclopentadienato [50] Fe(III)-curcumin [51] Prodrugs containing Co(III)-curcumin [52] Curcumin-2-aminophenol [53] Curcumin -Hg(II) complex in solution [54] Curcumin -M , M = Tc, Re [55] Mesoporous silica nanoparticles [56] Ga (III) -diketone (CUM)complex [57] (CUM)-based M(II) complexes as anticancer agents [58] DNA nanotechnology Cu(II)/Ni(II)/Zn(II)-curcumin-conjugated DNA complexes [59] cyclodextrins and conjugating it with silver nanoparticles [60] curcumin -Schiff base with various metal ions complexes ,M= Al(III), Mn(II), Fe(III), Co(II),Ni(II), Cu(II), Ag(I), Cd(II), Hg(II), and Pb(II) [61] Hexadentate (N 4 O 2 donor) Schiff base ligands derived from curcumin with some transition and non-transition metal cations [62] Schiff Base Derived Curcumin and L-Tyrosine with Al(III), Ag(I), and Pb(II) Metal Ions [63]…”