Antibacterial activity of metal complexes based on cinnamaldehyde thiosemicarbazone analogues

Bisceglie, Franco; Bacci, C.; Vismarra, Alice; Barilli, Elena; Pioli, Marianna; Orsoni, Nicolò; Pelosi, Giorgio

doi:10.1016/j.jinorgbio.2019.110888

Cited by 46 publications

(19 citation statements)

References 23 publications

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“…Thiosemicarbazones BeTS, BeTS-dm, CiTS and CiTS-dm (Fig. 1 ) were obtained in high yields by reacting benzaldehyde or cinnamaldehyde and thiosemicarbazide or 4,4-dimethyl-3-thiosemicarbazide 29 , 31 . The modification at the NH 2 terminal moiety was designed to highlight how a modulation in lipophilicity and hydrogen-bonding capabilities could impact activity.…”

Section: Resultsmentioning

confidence: 99%

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Sisters in structure but different in character, some benzaldehyde and cinnamaldehyde derivatives differentially tune Aspergillus flavus secondary metabolism

Bisceglie

Degola

Rogolino

et al. 2020

Sci Rep

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Great are the expectations for a new generation of antimicrobials, and strenuous are the research efforts towards the exploration of diverse molecular scaffolds—possibly of natural origin – aimed at the synthesis of new compounds against the spread of hazardous fungi. Also high but winding are the paths leading to the definition of biological targets specifically fitting the drug’s structural characteristics. The present study is addressed to inspect differential biological behaviours of cinnamaldehyde and benzaldehyde thiosemicarbazone scaffolds, exploiting the secondary metabolism of the mycotoxigenic phytopathogen Aspergillus flavus. Interestingly, owing to modifications on the parent chemical scaffold, some thiosemicarbazones displayed an increased specificity against one or more developmental processes (conidia germination, aflatoxin biosynthesis, sclerotia production) of A. flavus biology. Through the comparative analysis of results, the ligand-based screening strategy here described has allowed us to delineate which modifications are more promising for distinct purposes: from the control of mycotoxins contamination in food and feed commodities, to the environmental management of microbial pathogens, to the investigation of specific structure–activity features for new generation drug discovery.

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Section: Resultsmentioning

confidence: 99%

“…The synthesis of the TSs (Fig. 1 ) was accomplished following a protocol we have previously reported 29 , 31 . Briefly, the aldehyde was dissolved in hot ethanol and added of few drops of glacial acetic acid.…”

Section: Methodsmentioning

confidence: 99%

Sisters in structure but different in character, some benzaldehyde and cinnamaldehyde derivatives differentially tune Aspergillus flavus secondary metabolism

Bisceglie

Degola

Rogolino

et al. 2020

Sci Rep

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“…The peculiarity of these complexes is their ability to release the monodentate ligand when irradiated with UVA light. The photodissociation and the release of the pyridine ligand induces the formation of the aqua species [(η 6 arene)Ru(N,N′)(OH2)] 2+ and this is the moiety that is effectively active inside the cell. The aim of this work is expanding and improving the original idea of Sadler and co-workers introducing a more elaborate monodentate ligand.…”

Section: Introductionmentioning

confidence: 99%

“…Our main interest has been focused on the development of ligands bearing nitrogen and sulfur as donor atoms, and on the synthesis of their metal complexes [4][5][6][7][8]. These compounds, mainly belonging to the class of thiosemicarbazones [9], are known for their wide range of biological activities and for their ability to chelate metal ions.…”

Section: Introductionmentioning

confidence: 99%

A New Photoactivatable Ruthenium(II) Complex with an Asymmetric Bis-Thiocarbohydrazone: Chemical and Biological Investigations

et al. 2021

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The synthesis, photoactivation and biological activity of a new piano-stool Ru(II) complex is herein reported. The peculiarity of this complex is that its monodentate ligand which undergoes the photodissociation is an asymmetric bis-thiocarbohydrazone ligand that possesses a pyridine moiety binding to Ru(II) and the other moiety contains a quinoline that endows the ligand with the capacity of chelating other metal ions. In this way, upon dissociation, the ligand can be released in the form of a metal complex. In this article, the double ability of this new Ru(II) complex to photorelease the ligand and to chelate copper and nickel is explored and confirmed. The biological activity of this compound is studied in cell line A549 revealing that, after irradiation, proliferation inhibition is reached at very low half maximal inhibitory concentration (IC50) values. Further, biological assays reveal that the dinuclear complex containing Ni is internalized in cells.

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“…A recent study 15 reported the antibacterial activity of cinnamaldehyde thiosemicarbazones against the bacterial stains, such as E. coli and K. pneumoniae. In this study they tested the antibacterial activity of thiosemicarbazone ligands and their Cu(II) and Zn(II) complexes.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization of Copper Complexes of 9H-Carbazole-3-carbaldehyde-4-phenylthiosemicarbazone, 10-Hexyl-10-H-phenothiazine-3-carbaldehyde-4-phenylthio semicarbazone and 2-Thiophenecarboxaldehyde-4-methyl- thiosemicarbazone and Anti-bacterial Activity Studies of Ligands and Complexes

Jyothi

Farook²,

Madhuri

et al. 2020

Orient. J. Chem

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In Coordination chemistry metal chelating agents has a vital role, among them thiosemicarbazones occupies an important place due to their a range of applications in different fields, such as analytical and biological. In the literature we can find many thiosemicarbazones which has a wide range of applications both in pharmacy and chemical fields. But still there is a scope is there to synthesize new thiosemicarbazone ligands and their metal complexes due to their utility is still there in modern chemistry also. In this present study we synthesized the copper(II) complexes of 9H-Carbazole-3-carbaldehyde-4-phenylthiosemicarbazone, 10-hexyl-10-H-phenothiazine-3-carbaldehyde-4-phenylthiosemicarbazone and 2-thiophenecarboxalde-hyde-4-methylthiosemicarbazone and these complexes are characterized with FT-IR, XRD analysis and thermal stabilities of the both ligands and complexes are compared with thermogravimetric analysis studies. Finally the antibacterial activities of both chelating agents and their metal complexes are tested with two Gram-positive bacterial stains, such as Bacillus subtilis, Staphylococcus aureus and two Gram-negative bacterial stains, Pseudomonas aeruginosa, Escherichia coli.

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Antibacterial activity of metal complexes based on cinnamaldehyde thiosemicarbazone analogues

Cited by 46 publications

References 23 publications

Sisters in structure but different in character, some benzaldehyde and cinnamaldehyde derivatives differentially tune Aspergillus flavus secondary metabolism

Sisters in structure but different in character, some benzaldehyde and cinnamaldehyde derivatives differentially tune Aspergillus flavus secondary metabolism

A New Photoactivatable Ruthenium(II) Complex with an Asymmetric Bis-Thiocarbohydrazone: Chemical and Biological Investigations

Synthesis, Characterization of Copper Complexes of 9H-Carbazole-3-carbaldehyde-4-phenylthiosemicarbazone, 10-Hexyl-10-H-phenothiazine-3-carbaldehyde-4-phenylthio semicarbazone and 2-Thiophenecarboxaldehyde-4-methyl- thiosemicarbazone and Anti-bacterial Activity Studies of Ligands and Complexes

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