A new Cu(II)-O-Carvacrotinate complex: Synthesis, characterization and biological activity

Manas Sutradhar, Alexandra R. Fernandes, Fabiana Paradinha, Patricia Rijo, Catarina Garcia, Catarina Roma-Rodrigues, Armando J. L. Pombeiro, Adília Januário Charmier

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Herein, we report the first example of the synthesis of a novel type of Cu(II) complex based on a natural product ligand derived from carvacrol. The copper(II) complex [Cu(DCA) 2 (EtOH)] 2 ·2EtOH (1, HDCA[dbnd]O-carvacrotinic acid) has been synthesized and characterized by elemental analysis, IR spectroscopy, ESI-MS and single crystal X-ray analysis. Complex 1 and the carvacrotinic acid (2, HDCA) have been studied towards their antimicrobial and antiproliferative activities. For both compounds the antimicrobial activity was assessed against a panel of Gram-positive and Gram-negative bacteria and yeasts. The microdilution method allowed the determination of their Minimum Inhibitory Concentration (MIC) and minimum bactericidal concentration (MBC). Interestingly, both compounds seem to be more effective on yeasts rather than bacteria especially against C. albicans. Regarding the antimicrobial properties, the compounds appear to present a bacteriostatic behaviour, rather than bactericide. The antiproliferative effect of complex 1, O-carvacrotinic acid (HDCA) 2 and carvacrol (CA) 3 used as a reference to compare their antitumoral activity, was examined in 4 human tumor cell lines (ovarian carcinoma (A2780), colorectal carcinoma (HCT116), lung adenocarcinoma (A549) and breast adenocarcinoma (MCF7)) and in normal human primary fibroblasts. Complex 1 exhibits a moderate cytotoxic activity against ovarian carcinoma cells (A2780), with no cytotoxicity in normal primary human fibroblasts. The moderate cytotoxicity observed in A2780 cells was due to an increase of cell apoptosis.

Original languageEnglish
Pages (from-to)31-37
Number of pages7
JournalJournal of Inorganic Biochemistry
Volume190
DOIs
Publication statusPublished - 1 Jan 2019

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Bioactivity
Fibroblasts
Cytotoxicity
Yeast
Acids
Bacteria
Yeasts
Cells
Bactericides
Carcinoma
X ray analysis
Microbial Sensitivity Tests
Tumor Cell Line
Biological Products
Gram-Negative Bacteria
Tumors
Copper
Colorectal Neoplasms
Infrared spectroscopy
Spectrum Analysis

Keywords

  • Antimicrobial activity
  • Antiproliferative agent
  • Carvacrol
  • Cu(II) complex
  • Human tumor cell lines
  • O-carvacrotinic acid

Cite this

Sutradhar, Manas ; Fernandes, Alexandra R. ; Paradinha, Fabiana ; Rijo, Patricia ; Garcia, Catarina ; Roma-Rodrigues, Catarina ; Pombeiro, Armando J. L. ; Charmier, Adília Januário. / A new Cu(II)-O-Carvacrotinate complex: Synthesis, characterization and biological activity. In: Journal of Inorganic Biochemistry. 2019 ; Vol. 190. pp. 31-37.
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A new Cu(II)-O-Carvacrotinate complex: Synthesis, characterization and biological activity. / Sutradhar, Manas; Fernandes, Alexandra R.; Paradinha, Fabiana; Rijo, Patricia; Garcia, Catarina; Roma-Rodrigues, Catarina; Pombeiro, Armando J. L.; Charmier, Adília Januário.

In: Journal of Inorganic Biochemistry, Vol. 190, 01.01.2019, p. 31-37.

Research output: Contribution to journalArticle

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T1 - A new Cu(II)-O-Carvacrotinate complex: Synthesis, characterization and biological activity

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AU - Fernandes, Alexandra R.

AU - Paradinha, Fabiana

AU - Rijo, Patricia

AU - Garcia, Catarina

AU - Roma-Rodrigues, Catarina

AU - Pombeiro, Armando J. L.

AU - Charmier, Adília Januário

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N2 - Herein, we report the first example of the synthesis of a novel type of Cu(II) complex based on a natural product ligand derived from carvacrol. The copper(II) complex [Cu(DCA) 2 (EtOH)] 2 ·2EtOH (1, HDCA[dbnd]O-carvacrotinic acid) has been synthesized and characterized by elemental analysis, IR spectroscopy, ESI-MS and single crystal X-ray analysis. Complex 1 and the carvacrotinic acid (2, HDCA) have been studied towards their antimicrobial and antiproliferative activities. For both compounds the antimicrobial activity was assessed against a panel of Gram-positive and Gram-negative bacteria and yeasts. The microdilution method allowed the determination of their Minimum Inhibitory Concentration (MIC) and minimum bactericidal concentration (MBC). Interestingly, both compounds seem to be more effective on yeasts rather than bacteria especially against C. albicans. Regarding the antimicrobial properties, the compounds appear to present a bacteriostatic behaviour, rather than bactericide. The antiproliferative effect of complex 1, O-carvacrotinic acid (HDCA) 2 and carvacrol (CA) 3 used as a reference to compare their antitumoral activity, was examined in 4 human tumor cell lines (ovarian carcinoma (A2780), colorectal carcinoma (HCT116), lung adenocarcinoma (A549) and breast adenocarcinoma (MCF7)) and in normal human primary fibroblasts. Complex 1 exhibits a moderate cytotoxic activity against ovarian carcinoma cells (A2780), with no cytotoxicity in normal primary human fibroblasts. The moderate cytotoxicity observed in A2780 cells was due to an increase of cell apoptosis.

AB - Herein, we report the first example of the synthesis of a novel type of Cu(II) complex based on a natural product ligand derived from carvacrol. The copper(II) complex [Cu(DCA) 2 (EtOH)] 2 ·2EtOH (1, HDCA[dbnd]O-carvacrotinic acid) has been synthesized and characterized by elemental analysis, IR spectroscopy, ESI-MS and single crystal X-ray analysis. Complex 1 and the carvacrotinic acid (2, HDCA) have been studied towards their antimicrobial and antiproliferative activities. For both compounds the antimicrobial activity was assessed against a panel of Gram-positive and Gram-negative bacteria and yeasts. The microdilution method allowed the determination of their Minimum Inhibitory Concentration (MIC) and minimum bactericidal concentration (MBC). Interestingly, both compounds seem to be more effective on yeasts rather than bacteria especially against C. albicans. Regarding the antimicrobial properties, the compounds appear to present a bacteriostatic behaviour, rather than bactericide. The antiproliferative effect of complex 1, O-carvacrotinic acid (HDCA) 2 and carvacrol (CA) 3 used as a reference to compare their antitumoral activity, was examined in 4 human tumor cell lines (ovarian carcinoma (A2780), colorectal carcinoma (HCT116), lung adenocarcinoma (A549) and breast adenocarcinoma (MCF7)) and in normal human primary fibroblasts. Complex 1 exhibits a moderate cytotoxic activity against ovarian carcinoma cells (A2780), with no cytotoxicity in normal primary human fibroblasts. The moderate cytotoxicity observed in A2780 cells was due to an increase of cell apoptosis.

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KW - Antiproliferative agent

KW - Carvacrol

KW - Cu(II) complex

KW - Human tumor cell lines

KW - O-carvacrotinic acid

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JO - Journal of Inorganic Biochemistry

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