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 |
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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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[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%.</description><identifier>ISSN: 0141-8130</identifier><identifier>EISSN: 1879-0003</identifier><identifier>DOI: 10.1016/j.ijbiomac.2019.06.115</identifier><identifier>PMID: 31220500</identifier><language>eng</language><publisher>Netherlands: Elsevier B.V</publisher><subject>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</subject><ispartof>International journal of biological macromolecules, 2019-09, Vol.136, p.738-754</ispartof><rights>2019 Elsevier B.V.</rights><rights>Copyright © 2019 Elsevier B.V. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c368t-16c4ced8cffda80823929ff28502c3be23aa2f5af6ca2177cf7813a0a93c1b4f3</citedby><cites>FETCH-LOGICAL-c368t-16c4ced8cffda80823929ff28502c3be23aa2f5af6ca2177cf7813a0a93c1b4f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ijbiomac.2019.06.115$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31220500$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Manimohan, Murugaiyan</creatorcontrib><creatorcontrib>Pugalmani, Sivashanmugam</creatorcontrib><creatorcontrib>Sithique, Mohamed Aboobucker</creatorcontrib><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</title><title>International journal of biological macromolecules</title><addtitle>Int J Biol Macromol</addtitle><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%.</description><subject>Albumins - chemistry</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Anti-Inflammatory Agents - chemical synthesis</subject><subject>Anti-Inflammatory Agents - chemistry</subject><subject>Anti-Inflammatory Agents - pharmacology</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>Antioxidants - chemical synthesis</subject><subject>Antioxidants - chemistry</subject><subject>Antioxidants - pharmacology</subject><subject>Chemistry Techniques, Synthetic</subject><subject>Chitosan - analogs & derivatives</subject><subject>Chitosan - chemistry</subject><subject>Coordination Complexes - chemical synthesis</subject><subject>Coordination Complexes - chemistry</subject><subject>Coordination Complexes - pharmacology</subject><subject>Copper - chemistry</subject><subject>Hydrazines - chemistry</subject><subject>In-situ reaction</subject><subject>Ligands</subject><subject>Nitrogen - chemistry</subject><subject>Oxygen - chemistry</subject><subject>Phosphomolybdenum method</subject><subject>Protein Denaturation - drug effects</subject><subject>Schiff Bases - chemistry</subject><subject>Solubility</subject><subject>Thermal stability</subject><subject>Water - chemistry</subject><subject>Water soluble macromolecule Schiff base</subject><issn>0141-8130</issn><issn>1879-0003</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkduO0zAQhiMEYsvCK6x8uUgk-JAjV0DFodKKXixcWxNnTF05cbGdsuGdeEdcusstkmVbnu-f8cyfZVeMFoyy-vW-MPveuBFUwSnrCloXjFWPshVrmy6nlIrH2YqykuUtE_QiexbCPr3WFWufZheCcU4rSlfZ7_fGWffdKLB2IaCiOSKZ3BEt-fLqtLZkcJPzJHoz4BQhIvmZNk-Cs3NvkeyWwcOvFCQ9BBzINlfge3e3jBh3iyVqZ6ILMJHbdNP6L0XWM7nebF6SxEBC3HiweIfhDbldprjDYAKBaUha8OlP6E2AaNz0PHuiwQZ8cX9eZt8-fvi6_pzfbD9t1u9uciXqNuasVqXCoVVaD9DSlouOd1rztqJciR65AOC6Al0r4KxplG7SlIBCJxTrSy0us-tz3oN3P2YMUY4mKLQWJnRzkJyXVV2VouEJrc-o8i4Ej1oevBnBL5JRebJK7uWDVfJklaS1TFYl4dV9jbkfcfgne_AmAW_PAKZOjwa9DMrglBozHlWUgzP_q_EHD8CrvA</recordid><startdate>20190901</startdate><enddate>20190901</enddate><creator>Manimohan, Murugaiyan</creator><creator>Pugalmani, Sivashanmugam</creator><creator>Sithique, Mohamed Aboobucker</creator><general>Elsevier B.V</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20190901</creationdate><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</title><author>Manimohan, Murugaiyan ; Pugalmani, Sivashanmugam ; Sithique, Mohamed Aboobucker</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c368t-16c4ced8cffda80823929ff28502c3be23aa2f5af6ca2177cf7813a0a93c1b4f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Albumins - chemistry</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Anti-Inflammatory Agents - chemical synthesis</topic><topic>Anti-Inflammatory Agents - chemistry</topic><topic>Anti-Inflammatory Agents - pharmacology</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - pharmacology</topic><topic>Antioxidants - chemical synthesis</topic><topic>Antioxidants - chemistry</topic><topic>Antioxidants - pharmacology</topic><topic>Chemistry Techniques, Synthetic</topic><topic>Chitosan - analogs & derivatives</topic><topic>Chitosan - chemistry</topic><topic>Coordination Complexes - chemical synthesis</topic><topic>Coordination Complexes - chemistry</topic><topic>Coordination Complexes - pharmacology</topic><topic>Copper - chemistry</topic><topic>Hydrazines - chemistry</topic><topic>In-situ reaction</topic><topic>Ligands</topic><topic>Nitrogen - chemistry</topic><topic>Oxygen - chemistry</topic><topic>Phosphomolybdenum method</topic><topic>Protein Denaturation - drug effects</topic><topic>Schiff Bases - chemistry</topic><topic>Solubility</topic><topic>Thermal stability</topic><topic>Water - chemistry</topic><topic>Water soluble macromolecule Schiff base</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Manimohan, Murugaiyan</creatorcontrib><creatorcontrib>Pugalmani, Sivashanmugam</creatorcontrib><creatorcontrib>Sithique, Mohamed Aboobucker</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>International journal of biological macromolecules</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Manimohan, Murugaiyan</au><au>Pugalmani, Sivashanmugam</au><au>Sithique, Mohamed Aboobucker</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Biologically active novel N, N, O donor tridentate water soluble hydrazide based O-carboxymethyl chitosan Schiff base Cu (II) metal complexes: Synthesis and characterisation</atitle><jtitle>International journal of biological macromolecules</jtitle><addtitle>Int J Biol Macromol</addtitle><date>2019-09-01</date><risdate>2019</risdate><volume>136</volume><spage>738</spage><epage>754</epage><pages>738-754</pages><issn>0141-8130</issn><eissn>1879-0003</eissn><abstract>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%.</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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