Synthesis, Characterization and Evaluation of the Antibacterial and Antitumor Activity of HalogenatedSalen Copper (II) Complexes derived from Camphoric Acid

Platinum metal complexes are the most common chemotherapeutics currently used in cancer treatment. However, the frequent adverse effects, as well as acquired resistance by tumor cells, urge the development of effective alternatives. In the recent past, copper complexes with Schiff base ligands have...

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Veröffentlicht in:Applied organometallic chemistry 2020-05, Vol.34 (5), p.n/a
Hauptverfasser: Pires, Ana Salomé, Batista, João, Murtinho, Dina, Nogueira, Célia, Karamysheva, Anna, Luísa Ramos, M., Milne, Bruce F., Tavares, Nuno Tiago, Gonçalves, José, Gonçalves, Ana Cristina, Abrantes, Ana Margarida, Soares, Rui, Gonçalves, Teresa, Botelho, Maria Filomena, Silva Serra, M. Elisa
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container_issue 5
container_start_page
container_title Applied organometallic chemistry
container_volume 34
creator Pires, Ana Salomé
Batista, João
Murtinho, Dina
Nogueira, Célia
Karamysheva, Anna
Luísa Ramos, M.
Milne, Bruce F.
Tavares, Nuno Tiago
Gonçalves, José
Gonçalves, Ana Cristina
Abrantes, Ana Margarida
Soares, Rui
Gonçalves, Teresa
Botelho, Maria Filomena
Silva Serra, M. Elisa
description Platinum metal complexes are the most common chemotherapeutics currently used in cancer treatment. However, the frequent adverse effects, as well as acquired resistance by tumor cells, urge the development of effective alternatives. In the recent past, copper complexes with Schiff base ligands have emerged as good alternatives, showing interesting results. Accordingly, and in continuation of previous studies in this area, three new camphoric acid‐derived halogenated salen ligands and their corresponding Cu (II) complexes were synthesized and their antitumor activity was evaluated in order to determine the influence of the type and number of halogens present (Br, Cl). The in vitro cytotoxic activity was screened against colorectal WiDr and LS1034 and against breast MCF‐7 and HCC1806 cancer cell lines. The results proved the halogenated complexes to be very efficient, the tetrachlorinated Cu (II) complex being the most promising, presenting IC50 of 0.63–1.09 μM for the cell lines studied. The complex also shows selectivity to colorectal cancer cells compared to non‐tumor colon cells. It is worth highlighting that the tetrachlorinated Cu (II) complex, our most efficient complex, shows a significantly more powerful antitumor effect than the reference drugs currently used in conventional chemotherapy. The halogenated salen and corresponding complexes were also screened for their antimicrobial activity against four bacterial species‐Staphylococcus aureus, Enterococcus faecalis, Escherichia coli and Pseudomonas aeruginosa‐and four fungal species‐Candida albicans, Candida glabrata, Aspergillus fumigatus and Alternaria alternata. The compounds were found to exhibit moderate to strong antibacterial activity against the bacterial strains studied. NMR studies and theoretical calculations provided some insight into the structure of the ligands and copper complexes. Considering the results presented herein, our work validates the potential use of copper‐based chemotherapeutics as alternatives for cancer treatment. New camphoric acid‐derived halogenated salen ligands and their Cu (II) complexes were synthesized and evaluated for antitumor and antimicrobial activity. Our most efficient complex shows a significantly more powerful antitumor effect (IC50 0.63–1.09 μM) than the reference drugs currently used in conventional chemotherapy. The complexes and free ligands exhibit moderate to strong antibacterial activity. NMR and theoretical studies provided some structural insig
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Elisa</creator><creatorcontrib>Pires, Ana Salomé ; Batista, João ; Murtinho, Dina ; Nogueira, Célia ; Karamysheva, Anna ; Luísa Ramos, M. ; Milne, Bruce F. ; Tavares, Nuno Tiago ; Gonçalves, José ; Gonçalves, Ana Cristina ; Abrantes, Ana Margarida ; Soares, Rui ; Gonçalves, Teresa ; Botelho, Maria Filomena ; Silva Serra, M. Elisa</creatorcontrib><description>Platinum metal complexes are the most common chemotherapeutics currently used in cancer treatment. However, the frequent adverse effects, as well as acquired resistance by tumor cells, urge the development of effective alternatives. In the recent past, copper complexes with Schiff base ligands have emerged as good alternatives, showing interesting results. Accordingly, and in continuation of previous studies in this area, three new camphoric acid‐derived halogenated salen ligands and their corresponding Cu (II) complexes were synthesized and their antitumor activity was evaluated in order to determine the influence of the type and number of halogens present (Br, Cl). The in vitro cytotoxic activity was screened against colorectal WiDr and LS1034 and against breast MCF‐7 and HCC1806 cancer cell lines. The results proved the halogenated complexes to be very efficient, the tetrachlorinated Cu (II) complex being the most promising, presenting IC50 of 0.63–1.09 μM for the cell lines studied. The complex also shows selectivity to colorectal cancer cells compared to non‐tumor colon cells. It is worth highlighting that the tetrachlorinated Cu (II) complex, our most efficient complex, shows a significantly more powerful antitumor effect than the reference drugs currently used in conventional chemotherapy. The halogenated salen and corresponding complexes were also screened for their antimicrobial activity against four bacterial species‐Staphylococcus aureus, Enterococcus faecalis, Escherichia coli and Pseudomonas aeruginosa‐and four fungal species‐Candida albicans, Candida glabrata, Aspergillus fumigatus and Alternaria alternata. The compounds were found to exhibit moderate to strong antibacterial activity against the bacterial strains studied. NMR studies and theoretical calculations provided some insight into the structure of the ligands and copper complexes. Considering the results presented herein, our work validates the potential use of copper‐based chemotherapeutics as alternatives for cancer treatment. New camphoric acid‐derived halogenated salen ligands and their Cu (II) complexes were synthesized and evaluated for antitumor and antimicrobial activity. 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Elisa</creatorcontrib><title>Synthesis, Characterization and Evaluation of the Antibacterial and Antitumor Activity of HalogenatedSalen Copper (II) Complexes derived from Camphoric Acid</title><title>Applied organometallic chemistry</title><description>Platinum metal complexes are the most common chemotherapeutics currently used in cancer treatment. However, the frequent adverse effects, as well as acquired resistance by tumor cells, urge the development of effective alternatives. In the recent past, copper complexes with Schiff base ligands have emerged as good alternatives, showing interesting results. Accordingly, and in continuation of previous studies in this area, three new camphoric acid‐derived halogenated salen ligands and their corresponding Cu (II) complexes were synthesized and their antitumor activity was evaluated in order to determine the influence of the type and number of halogens present (Br, Cl). 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Elisa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, Characterization and Evaluation of the Antibacterial and Antitumor Activity of HalogenatedSalen Copper (II) Complexes derived from Camphoric Acid</atitle><jtitle>Applied organometallic chemistry</jtitle><date>2020-05</date><risdate>2020</risdate><volume>34</volume><issue>5</issue><epage>n/a</epage><issn>0268-2605</issn><eissn>1099-0739</eissn><abstract>Platinum metal complexes are the most common chemotherapeutics currently used in cancer treatment. However, the frequent adverse effects, as well as acquired resistance by tumor cells, urge the development of effective alternatives. In the recent past, copper complexes with Schiff base ligands have emerged as good alternatives, showing interesting results. Accordingly, and in continuation of previous studies in this area, three new camphoric acid‐derived halogenated salen ligands and their corresponding Cu (II) complexes were synthesized and their antitumor activity was evaluated in order to determine the influence of the type and number of halogens present (Br, Cl). The in vitro cytotoxic activity was screened against colorectal WiDr and LS1034 and against breast MCF‐7 and HCC1806 cancer cell lines. The results proved the halogenated complexes to be very efficient, the tetrachlorinated Cu (II) complex being the most promising, presenting IC50 of 0.63–1.09 μM for the cell lines studied. The complex also shows selectivity to colorectal cancer cells compared to non‐tumor colon cells. It is worth highlighting that the tetrachlorinated Cu (II) complex, our most efficient complex, shows a significantly more powerful antitumor effect than the reference drugs currently used in conventional chemotherapy. The halogenated salen and corresponding complexes were also screened for their antimicrobial activity against four bacterial species‐Staphylococcus aureus, Enterococcus faecalis, Escherichia coli and Pseudomonas aeruginosa‐and four fungal species‐Candida albicans, Candida glabrata, Aspergillus fumigatus and Alternaria alternata. The compounds were found to exhibit moderate to strong antibacterial activity against the bacterial strains studied. NMR studies and theoretical calculations provided some insight into the structure of the ligands and copper complexes. Considering the results presented herein, our work validates the potential use of copper‐based chemotherapeutics as alternatives for cancer treatment. New camphoric acid‐derived halogenated salen ligands and their Cu (II) complexes were synthesized and evaluated for antitumor and antimicrobial activity. Our most efficient complex shows a significantly more powerful antitumor effect (IC50 0.63–1.09 μM) than the reference drugs currently used in conventional chemotherapy. The complexes and free ligands exhibit moderate to strong antibacterial activity. NMR and theoretical studies provided some structural insight.</abstract><cop>Chichester</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/aoc.5569</doi><tpages>18</tpages><orcidid>https://orcid.org/0000-0002-4562-7072</orcidid><oa>free_for_read</oa></addata></record>
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subjects Anticancer properties
antimicrobial activity
Biotechnology
Cancer
Cancer therapies
Chemistry
Chemotherapy
Colon
Coordination compounds
Copper
Copper compounds
copper salens
cytotoxic activity
E coli
Halogens
Imines
ligand geometry optimization
Ligands
NMR
NMR studies
Nuclear magnetic resonance
Platinum
Pseudomonas aeruginosa
Selectivity
title Synthesis, Characterization and Evaluation of the Antibacterial and Antitumor Activity of HalogenatedSalen Copper (II) Complexes derived from Camphoric Acid
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