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A bis-chelate o-vanillin-2-ethano-lamine copper(II) complex bearing both imine and amine forms of the ligand.

ABSTRACT: The mol-ecular bis-chelate complex (2-{[(2-hy-droxy-ethyl-κO)amino-κN]meth-yl}-6-meth-oxy-phenolato-κO)(2-{[(2-hy-droxy-eth-yl)imino-κN]meth-yl}-6-meth-oxy-phenolato-κO)copper(II), [Cu(C₁₀H₁₄NO₃)(C₁₀H₁₂NO₃)] or [Cu(HL ^im)(HL ^am); HL ^im = C₁₀H₁₄NO₃; HL ^am = C₁₀H₁₂NO₃, represents the first compound containing a salicyl-idene-2-ethano-lamine type ligand in both imino HL ^im (Schiff base) and amino HL ^am (reduced Schiff base) forms that has been structurally characterized on the basis of X-ray data. Two mol-ecules of the monodeprotonated ligands coordinate the Cu^II ion in an (N,O _phen)-bidentate and an (N,O _phen,O _alc)-tridentate fashion in the case of the imino and amino forms, respectively. The shape of the CuN₂O₃ coordination polyhedron is a distorted square-pyramid (geometry index τ₅ = 0.26). Inter-molecular N-H⋯O and O-H⋯O hydrogen bonds, involving H atoms of the amino and hy-droxy-ethyl groups, create a two-dimensional supra-molecular array extending parallel to (010).

SUBMITTER: Plyuta N

PROVIDER: S-EPMC8647731 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:Nano-micelles are self-assembling colloidal dispersions applied to enhance the anticancer efficacy of chemotherapeutic agents. In this study, the conjugate of quarternized chitosan and vanillin imine (QCS-Vani imine) was synthesized using the reaction of a Schiff base characterized by proton-NMR (1HNMR), UV-Vis spectroscopy, and FT-IR. The critical micelle concentration (CMC), particle size, and zeta potential of the resulting product were determined. The QCS-Vani imine conjugate was used as a carrier for the development of curcumin-loaded nano-micelles, and their entrapment efficiency (%EE), drug-loading capacity (%LC) and in vitro release were investigated using HPLC analysis. Moreover, the nano-micelles containing curcumin were combined with various concentrations of cisplatin and evaluated for a possible anticancer synergistic effect. The anticancer activity was evaluated against lung cancer A549 and mouse fibroblast L929 cell lines. The percent yield (%) of the QCS-Vani imine conjugate was 93.18%. The curcumin-loaded QCS-Vani imine nano-micelles were characterized and found to have a spherical shape (by TEM) with size < 200 nm (by DLS) with high %EE up to 67.61% and %LC up to 6.15 ± 0.41%. The loaded lyophilized powder of the nano-micelles was more stable at 4 °C than at room temperature during 120 days of storage. pH-sensitive release properties were observed to have a higher curcumin release at pH 5.5 (cancer environment) than at pH 7.4 (systemic environment). Curcumin-loaded QCS-Vani imine nano-micelles showed higher cytotoxicity and selectivity toward lung cancer A549 cell lines and exhibited lower toxicity toward the normal cell (H9C2) than pure curcumin. Moreover, the curcumin-loaded QCS-Vani imine nano-micelles exhibited an enhanced property of inducing cell cycle arrest during the S-phase against A549 cells and showed prominently induced apoptosis in lung cancer cells compared to that with curcumin. The co-treatment of cisplatin with curcumin-loaded QCS-Vani imine nano-micelles presented an enhanced anticancer effect, showing 8.66 ± 0.88 μM as the IC50 value, in comparison to the treatment with cisplatin alone (14.22 ± 1.01 μM). These findings suggest that the developed QCS-Vani imine nano-micelle is a potential drug delivery system and could be a promising approach for treating lung cancer in combination with cisplatin.

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A bis-chelate o-vanillin-2-ethano-lamine copper(II) complex bearing both imine and amine forms of the ligand.

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