Biologically active novel N, N, O donor tridentate water soluble hydrazide based O-carboxymethyl chitosan Schiff base Cu (II) metal complexes: Synthesis and characterisation

Water soluble hydrazide based O-carboxymethyl chitosan Schiff base ligands have been prepared from chitosan and a mixture of benzoic acidhydrazide with β-diketone by carboxymethylation using mono chloroaceticacid (MCA) through in-situ reaction. The degree of deacetylation of chitosan was determined...

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Veröffentlicht in:International journal of biological macromolecules 2019-09, Vol.136, p.738-754
Hauptverfasser: Manimohan, Murugaiyan, Pugalmani, Sivashanmugam, Sithique, Mohamed Aboobucker
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Pugalmani, Sivashanmugam
Sithique, Mohamed Aboobucker
description Water soluble hydrazide based O-carboxymethyl chitosan Schiff base ligands have been prepared from chitosan and a mixture of benzoic acidhydrazide with β-diketone by carboxymethylation using mono chloroaceticacid (MCA) through in-situ reaction. The degree of deacetylation of chitosan was determined by elemental analysis and potentiometric titration. Schiff base ligands and the functional groups were characterised by FT-IR, 1H, and 13C NMR spectroscopic techniques. The crystallinity of ligands and complexes was evaluated by X-ray powder diffraction (XRD) studies. Thermal stability of all the synthesized compounds was investigated by thermo gravimetric analysis and differential thermal analysis (TGA-DTA) which revealed the presence of metal oxide (CuO) residue to elevate the temperature to >500 °C. Filed emission scanning electron microscopic (FESEM) analysis revealed that Cu (II) complexes were more amorphous in nature than chitosan and Schiff base ligands. Vibrating sample magnetometer (VSM) studies reported that the d9 configuration of the metal complex was paramagnetic in nature and the geometry of the complex was square pyramidal. The antimicrobial activity of the synthesized hydrazide Cu (II) complexes was characterised by agar plate method, anti-inflammatory study was characterised by egg albumin denaturation technique and total antioxidant activity was characterised by phosphomolybdenum method. [Display omitted] •Problems relating to water solubility of chitosan have been eliminated.•A novel kind of hydrazide based NNO-tridentate O-carboxymethyl chitosan Cu (II) complexes was prepared.•The in-situ synthesis of the complex was reduced the time factor about 50%.
doi_str_mv 10.1016/j.ijbiomac.2019.06.115
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The degree of deacetylation of chitosan was determined by elemental analysis and potentiometric titration. Schiff base ligands and the functional groups were characterised by FT-IR, 1H, and 13C NMR spectroscopic techniques. The crystallinity of ligands and complexes was evaluated by X-ray powder diffraction (XRD) studies. Thermal stability of all the synthesized compounds was investigated by thermo gravimetric analysis and differential thermal analysis (TGA-DTA) which revealed the presence of metal oxide (CuO) residue to elevate the temperature to &gt;500 °C. Filed emission scanning electron microscopic (FESEM) analysis revealed that Cu (II) complexes were more amorphous in nature than chitosan and Schiff base ligands. Vibrating sample magnetometer (VSM) studies reported that the d9 configuration of the metal complex was paramagnetic in nature and the geometry of the complex was square pyramidal. The antimicrobial activity of the synthesized hydrazide Cu (II) complexes was characterised by agar plate method, anti-inflammatory study was characterised by egg albumin denaturation technique and total antioxidant activity was characterised by phosphomolybdenum method. [Display omitted] •Problems relating to water solubility of chitosan have been eliminated.•A novel kind of hydrazide based NNO-tridentate O-carboxymethyl chitosan Cu (II) complexes was prepared.•The in-situ synthesis of the complex was reduced the time factor about 50%.</abstract><cop>Netherlands</cop><pub>Elsevier B.V</pub><pmid>31220500</pmid><doi>10.1016/j.ijbiomac.2019.06.115</doi><tpages>17</tpages></addata></record>
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subjects Albumins - chemistry
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Anti-Inflammatory Agents - chemical synthesis
Anti-Inflammatory Agents - chemistry
Anti-Inflammatory Agents - pharmacology
Antifungal Agents - chemical synthesis
Antifungal Agents - chemistry
Antifungal Agents - pharmacology
Antioxidants - chemical synthesis
Antioxidants - chemistry
Antioxidants - pharmacology
Chemistry Techniques, Synthetic
Chitosan - analogs & derivatives
Chitosan - chemistry
Coordination Complexes - chemical synthesis
Coordination Complexes - chemistry
Coordination Complexes - pharmacology
Copper - chemistry
Hydrazines - chemistry
In-situ reaction
Ligands
Nitrogen - chemistry
Oxygen - chemistry
Phosphomolybdenum method
Protein Denaturation - drug effects
Schiff Bases - chemistry
Solubility
Thermal stability
Water - chemistry
Water soluble macromolecule Schiff base
title Biologically active novel N, N, O donor tridentate water soluble hydrazide based O-carboxymethyl chitosan Schiff base Cu (II) metal complexes: Synthesis and characterisation
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