Synthesis, characterization, anticancer and antibacterial evaluation of Schiff base ligands derived from hydrazone and their transition metal complexes

In this paper, metal chelates of Schiff base derived from hydrazones have been prepared and characterized by 1HNMR, IR, UV–Vis spectroscopy and cyclic voltammetry. Single crystal X-ray crystallography studies confirm the structure of newly synthesized Schiff bases. The Schiff bases act as tridentate...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Inorganica Chimica Acta 2019-01, Vol.484, p.245-254
Hauptverfasser: Fekri, Roghayeh, Salehi, Mehdi, Asadi, Asadollah, Kubicki, Maciej
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 254
container_issue
container_start_page 245
container_title Inorganica Chimica Acta
container_volume 484
creator Fekri, Roghayeh
Salehi, Mehdi
Asadi, Asadollah
Kubicki, Maciej
description In this paper, metal chelates of Schiff base derived from hydrazones have been prepared and characterized by 1HNMR, IR, UV–Vis spectroscopy and cyclic voltammetry. Single crystal X-ray crystallography studies confirm the structure of newly synthesized Schiff bases. The Schiff bases act as tridentate ligands. The free ligands and metal compounds are screened for their antibacterial activities against Gram-positive and Gram-negative bacteria. Further the cytotoxic effect of the ligands and their metal compounds examined on cancer cell lines showed that the metal compounds exhibit better activity than ligands. [Display omitted] •Three new metal complexes of hydrazone Schiff bases were synthesized and characterized.•Structures for the complexes were determined by X-ray diffraction.•The cyclic voltammetry behavior of these compounds was discussed.•Complexes showed good antibacterial and anticancer activity. Copper(II), Nickel(II) and Cobalt(III) complexes with Schiff base ligands derived from hydrazone, (HL1 = (E)-N′-(pyridin-2-ylmethylene)benzohydrazide, H2L2 = (E)-2-(2-hydroxybenzylidene)hydrazine-1-carboxamide and HL3 = (E)-2-(pyridin-2-ylmethylene)hydrazine-1-carboxamide, were synthesized and spectroscopically characterized by FT-IR, 1H NMR, UV–Vis spectroscopy, X-ray crystallography and cyclic voltammetry. The synthesized compounds have been screened for their antibacterial activities against the bacterial species E. coli, K. pneumonia (Gram-negative) and S. aureus, B. subtilis (Gram-positive) by minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) methods. In vitro anticancer studies of the ligands and coordination compounds (1–3) using MTT assay was also done. Results show that the complexes (1–3) have higher antibacterial and anticancer activities than the respective free ligands.
doi_str_mv 10.1016/j.ica.2018.09.022
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2153602270</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0020169318307825</els_id><sourcerecordid>2153602270</sourcerecordid><originalsourceid>FETCH-LOGICAL-c325t-74c8d8683bd82ed3034367034402badcbb5d1fdcc5f10ea51efe6f3a27ff97c23</originalsourceid><addsrcrecordid>eNp9kMtKAzEUhoMoWKsP4C7gtjPm0rnhSoo3KLiorkMmObEp00lN0mL7Ir6usePaTS7w_d9JfoSuKckpoeXtKrdK5ozQOidNThg7QSNaVzzjrChO0YgQRjJaNvwcXYSwIoSTkhcj9L3Y93EJwYYJVkvppYrg7UFG6_oJln1M2l6BT0d9vLYDITsMO9ltjyB2Bi_U0hqDWxkAd_Yj4QHrBO5AY-PdGi_32suD6-GoSjOtx9HLPtijYg0xOZVbbzr4gnCJzozsAlz97WP0_vjwNnvO5q9PL7P7eabSx2JWTVWt67Lmra4ZaE74lJdVWqeEtVKrti00NVqpwlACsqBgoDRcssqYplKMj9HN4N1497mFEMXKbX2fRgpGC16mJpNujOhAKe9C8GDExtu19HtBifjtX6xEKkr89i9II1IqZe6GDKTn7yx4EZSF1KW2HlQU2tl_0j_oN5Hs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2153602270</pqid></control><display><type>article</type><title>Synthesis, characterization, anticancer and antibacterial evaluation of Schiff base ligands derived from hydrazone and their transition metal complexes</title><source>Access via ScienceDirect (Elsevier)</source><creator>Fekri, Roghayeh ; Salehi, Mehdi ; Asadi, Asadollah ; Kubicki, Maciej</creator><creatorcontrib>Fekri, Roghayeh ; Salehi, Mehdi ; Asadi, Asadollah ; Kubicki, Maciej</creatorcontrib><description>In this paper, metal chelates of Schiff base derived from hydrazones have been prepared and characterized by 1HNMR, IR, UV–Vis spectroscopy and cyclic voltammetry. Single crystal X-ray crystallography studies confirm the structure of newly synthesized Schiff bases. The Schiff bases act as tridentate ligands. The free ligands and metal compounds are screened for their antibacterial activities against Gram-positive and Gram-negative bacteria. Further the cytotoxic effect of the ligands and their metal compounds examined on cancer cell lines showed that the metal compounds exhibit better activity than ligands. [Display omitted] •Three new metal complexes of hydrazone Schiff bases were synthesized and characterized.•Structures for the complexes were determined by X-ray diffraction.•The cyclic voltammetry behavior of these compounds was discussed.•Complexes showed good antibacterial and anticancer activity. Copper(II), Nickel(II) and Cobalt(III) complexes with Schiff base ligands derived from hydrazone, (HL1 = (E)-N′-(pyridin-2-ylmethylene)benzohydrazide, H2L2 = (E)-2-(2-hydroxybenzylidene)hydrazine-1-carboxamide and HL3 = (E)-2-(pyridin-2-ylmethylene)hydrazine-1-carboxamide, were synthesized and spectroscopically characterized by FT-IR, 1H NMR, UV–Vis spectroscopy, X-ray crystallography and cyclic voltammetry. The synthesized compounds have been screened for their antibacterial activities against the bacterial species E. coli, K. pneumonia (Gram-negative) and S. aureus, B. subtilis (Gram-positive) by minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) methods. In vitro anticancer studies of the ligands and coordination compounds (1–3) using MTT assay was also done. Results show that the complexes (1–3) have higher antibacterial and anticancer activities than the respective free ligands.</description><identifier>ISSN: 0020-1693</identifier><identifier>EISSN: 1873-3255</identifier><identifier>DOI: 10.1016/j.ica.2018.09.022</identifier><language>eng</language><publisher>Amsterdam: Elsevier B.V</publisher><subject>Antibacterial study ; Anticancer activity ; Anticancer properties ; Chemical compounds ; Coordination compounds ; Copper compounds ; Crystal structure ; Crystallography ; E coli ; Fourier transforms ; Hydrazines ; Hydrazone ; Hydrazones ; Imines ; In vitro methods and tests ; Infrared spectroscopy ; Ligands ; NMR ; Nuclear magnetic resonance ; Spectral properties ; Spectrum analysis ; Synthesis ; Transition metal compounds ; X ray spectra</subject><ispartof>Inorganica Chimica Acta, 2019-01, Vol.484, p.245-254</ispartof><rights>2018 Elsevier B.V.</rights><rights>Copyright Elsevier Science Ltd. Jan 1, 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c325t-74c8d8683bd82ed3034367034402badcbb5d1fdcc5f10ea51efe6f3a27ff97c23</citedby><cites>FETCH-LOGICAL-c325t-74c8d8683bd82ed3034367034402badcbb5d1fdcc5f10ea51efe6f3a27ff97c23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ica.2018.09.022$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>Fekri, Roghayeh</creatorcontrib><creatorcontrib>Salehi, Mehdi</creatorcontrib><creatorcontrib>Asadi, Asadollah</creatorcontrib><creatorcontrib>Kubicki, Maciej</creatorcontrib><title>Synthesis, characterization, anticancer and antibacterial evaluation of Schiff base ligands derived from hydrazone and their transition metal complexes</title><title>Inorganica Chimica Acta</title><description>In this paper, metal chelates of Schiff base derived from hydrazones have been prepared and characterized by 1HNMR, IR, UV–Vis spectroscopy and cyclic voltammetry. Single crystal X-ray crystallography studies confirm the structure of newly synthesized Schiff bases. The Schiff bases act as tridentate ligands. The free ligands and metal compounds are screened for their antibacterial activities against Gram-positive and Gram-negative bacteria. Further the cytotoxic effect of the ligands and their metal compounds examined on cancer cell lines showed that the metal compounds exhibit better activity than ligands. [Display omitted] •Three new metal complexes of hydrazone Schiff bases were synthesized and characterized.•Structures for the complexes were determined by X-ray diffraction.•The cyclic voltammetry behavior of these compounds was discussed.•Complexes showed good antibacterial and anticancer activity. Copper(II), Nickel(II) and Cobalt(III) complexes with Schiff base ligands derived from hydrazone, (HL1 = (E)-N′-(pyridin-2-ylmethylene)benzohydrazide, H2L2 = (E)-2-(2-hydroxybenzylidene)hydrazine-1-carboxamide and HL3 = (E)-2-(pyridin-2-ylmethylene)hydrazine-1-carboxamide, were synthesized and spectroscopically characterized by FT-IR, 1H NMR, UV–Vis spectroscopy, X-ray crystallography and cyclic voltammetry. The synthesized compounds have been screened for their antibacterial activities against the bacterial species E. coli, K. pneumonia (Gram-negative) and S. aureus, B. subtilis (Gram-positive) by minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) methods. In vitro anticancer studies of the ligands and coordination compounds (1–3) using MTT assay was also done. Results show that the complexes (1–3) have higher antibacterial and anticancer activities than the respective free ligands.</description><subject>Antibacterial study</subject><subject>Anticancer activity</subject><subject>Anticancer properties</subject><subject>Chemical compounds</subject><subject>Coordination compounds</subject><subject>Copper compounds</subject><subject>Crystal structure</subject><subject>Crystallography</subject><subject>E coli</subject><subject>Fourier transforms</subject><subject>Hydrazines</subject><subject>Hydrazone</subject><subject>Hydrazones</subject><subject>Imines</subject><subject>In vitro methods and tests</subject><subject>Infrared spectroscopy</subject><subject>Ligands</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Spectral properties</subject><subject>Spectrum analysis</subject><subject>Synthesis</subject><subject>Transition metal compounds</subject><subject>X ray spectra</subject><issn>0020-1693</issn><issn>1873-3255</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kMtKAzEUhoMoWKsP4C7gtjPm0rnhSoo3KLiorkMmObEp00lN0mL7Ir6usePaTS7w_d9JfoSuKckpoeXtKrdK5ozQOidNThg7QSNaVzzjrChO0YgQRjJaNvwcXYSwIoSTkhcj9L3Y93EJwYYJVkvppYrg7UFG6_oJln1M2l6BT0d9vLYDITsMO9ltjyB2Bi_U0hqDWxkAd_Yj4QHrBO5AY-PdGi_32suD6-GoSjOtx9HLPtijYg0xOZVbbzr4gnCJzozsAlz97WP0_vjwNnvO5q9PL7P7eabSx2JWTVWt67Lmra4ZaE74lJdVWqeEtVKrti00NVqpwlACsqBgoDRcssqYplKMj9HN4N1497mFEMXKbX2fRgpGC16mJpNujOhAKe9C8GDExtu19HtBifjtX6xEKkr89i9II1IqZe6GDKTn7yx4EZSF1KW2HlQU2tl_0j_oN5Hs</recordid><startdate>20190101</startdate><enddate>20190101</enddate><creator>Fekri, Roghayeh</creator><creator>Salehi, Mehdi</creator><creator>Asadi, Asadollah</creator><creator>Kubicki, Maciej</creator><general>Elsevier B.V</general><general>Elsevier Science Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20190101</creationdate><title>Synthesis, characterization, anticancer and antibacterial evaluation of Schiff base ligands derived from hydrazone and their transition metal complexes</title><author>Fekri, Roghayeh ; Salehi, Mehdi ; Asadi, Asadollah ; Kubicki, Maciej</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c325t-74c8d8683bd82ed3034367034402badcbb5d1fdcc5f10ea51efe6f3a27ff97c23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Antibacterial study</topic><topic>Anticancer activity</topic><topic>Anticancer properties</topic><topic>Chemical compounds</topic><topic>Coordination compounds</topic><topic>Copper compounds</topic><topic>Crystal structure</topic><topic>Crystallography</topic><topic>E coli</topic><topic>Fourier transforms</topic><topic>Hydrazines</topic><topic>Hydrazone</topic><topic>Hydrazones</topic><topic>Imines</topic><topic>In vitro methods and tests</topic><topic>Infrared spectroscopy</topic><topic>Ligands</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Spectral properties</topic><topic>Spectrum analysis</topic><topic>Synthesis</topic><topic>Transition metal compounds</topic><topic>X ray spectra</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fekri, Roghayeh</creatorcontrib><creatorcontrib>Salehi, Mehdi</creatorcontrib><creatorcontrib>Asadi, Asadollah</creatorcontrib><creatorcontrib>Kubicki, Maciej</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Inorganica Chimica Acta</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fekri, Roghayeh</au><au>Salehi, Mehdi</au><au>Asadi, Asadollah</au><au>Kubicki, Maciej</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, characterization, anticancer and antibacterial evaluation of Schiff base ligands derived from hydrazone and their transition metal complexes</atitle><jtitle>Inorganica Chimica Acta</jtitle><date>2019-01-01</date><risdate>2019</risdate><volume>484</volume><spage>245</spage><epage>254</epage><pages>245-254</pages><issn>0020-1693</issn><eissn>1873-3255</eissn><abstract>In this paper, metal chelates of Schiff base derived from hydrazones have been prepared and characterized by 1HNMR, IR, UV–Vis spectroscopy and cyclic voltammetry. Single crystal X-ray crystallography studies confirm the structure of newly synthesized Schiff bases. The Schiff bases act as tridentate ligands. The free ligands and metal compounds are screened for their antibacterial activities against Gram-positive and Gram-negative bacteria. Further the cytotoxic effect of the ligands and their metal compounds examined on cancer cell lines showed that the metal compounds exhibit better activity than ligands. [Display omitted] •Three new metal complexes of hydrazone Schiff bases were synthesized and characterized.•Structures for the complexes were determined by X-ray diffraction.•The cyclic voltammetry behavior of these compounds was discussed.•Complexes showed good antibacterial and anticancer activity. Copper(II), Nickel(II) and Cobalt(III) complexes with Schiff base ligands derived from hydrazone, (HL1 = (E)-N′-(pyridin-2-ylmethylene)benzohydrazide, H2L2 = (E)-2-(2-hydroxybenzylidene)hydrazine-1-carboxamide and HL3 = (E)-2-(pyridin-2-ylmethylene)hydrazine-1-carboxamide, were synthesized and spectroscopically characterized by FT-IR, 1H NMR, UV–Vis spectroscopy, X-ray crystallography and cyclic voltammetry. The synthesized compounds have been screened for their antibacterial activities against the bacterial species E. coli, K. pneumonia (Gram-negative) and S. aureus, B. subtilis (Gram-positive) by minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) methods. In vitro anticancer studies of the ligands and coordination compounds (1–3) using MTT assay was also done. Results show that the complexes (1–3) have higher antibacterial and anticancer activities than the respective free ligands.</abstract><cop>Amsterdam</cop><pub>Elsevier B.V</pub><doi>10.1016/j.ica.2018.09.022</doi><tpages>10</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0020-1693
ispartof Inorganica Chimica Acta, 2019-01, Vol.484, p.245-254
issn 0020-1693
1873-3255
language eng
recordid cdi_proquest_journals_2153602270
source Access via ScienceDirect (Elsevier)
subjects Antibacterial study
Anticancer activity
Anticancer properties
Chemical compounds
Coordination compounds
Copper compounds
Crystal structure
Crystallography
E coli
Fourier transforms
Hydrazines
Hydrazone
Hydrazones
Imines
In vitro methods and tests
Infrared spectroscopy
Ligands
NMR
Nuclear magnetic resonance
Spectral properties
Spectrum analysis
Synthesis
Transition metal compounds
X ray spectra
title Synthesis, characterization, anticancer and antibacterial evaluation of Schiff base ligands derived from hydrazone and their transition metal complexes
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-26T13%3A06%3A05IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis,%20characterization,%20anticancer%20and%20antibacterial%20evaluation%20of%20Schiff%20base%20ligands%20derived%20from%20hydrazone%20and%20their%20transition%20metal%20complexes&rft.jtitle=Inorganica%20Chimica%20Acta&rft.au=Fekri,%20Roghayeh&rft.date=2019-01-01&rft.volume=484&rft.spage=245&rft.epage=254&rft.pages=245-254&rft.issn=0020-1693&rft.eissn=1873-3255&rft_id=info:doi/10.1016/j.ica.2018.09.022&rft_dat=%3Cproquest_cross%3E2153602270%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2153602270&rft_id=info:pmid/&rft_els_id=S0020169318307825&rfr_iscdi=true