Insight into the cytotoxicity of polynuclear Cu(I) camphor complexes

Fernandes, Tiago A.; Mendes, Filipa; Roseiro, Alexandra P. S.; Santos, Isabel; Carvalho, M. Fernanda N. N.

doi:10.1016/j.poly.2014.11.020

Cited by 22 publications

(15 citation statements)

References 24 publications

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“…However, this apparently small difference enforces steric modifications, that according to the results obtained drive the interaction with the biological receptors and consequently to the antimicrobial activities of the complexes. In a former work, camphorimine compounds L2 and L4 were used as ligands to prepare Cu(I) complexes and their anti-proliferative activity against the cancer cell line HT29 was studied [ 32 ]. Both complexes displayed high anti-proliferative activity, being the activity of the Cu(I) complex with ligand L2 higher compared to L4 .…”

Section: Resultsmentioning

confidence: 99%

“…The camphor derivatives were synthesized under air using conventional organic synthesis techniques. Complexes ( 4 – 8 ) [ 28 , 31 ] and ligands (L II , L IV -L VIII ) [ 32 , 33 ] were synthesized following published procedures. Camphor, camphorsulfonic acid and the appropriate amines were purchased from Sigma-Aldrich (St. Louis, MO, USA).…”

Section: Methodsmentioning

confidence: 99%

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Ag(I) camphorimine complexes with antimicrobial activity towards clinically important bacteria and species of the Candida genus

et al. 2017

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The present work follows a previous report describing the antibacterial activity of silver camphorimine complexes of general formula [Ag(NO3)L]. The synthesis and demonstration of the antifungal and antibacterial activity of three novel [Ag(NO3)L] complexes (named 1, 2 and 3) is herein demonstrated. This work also shows for the first time that the previously studied complexes (named 4 to 8) also exert antifungal activity. The antibacterial activity of complexes was evaluated against Staphylococcus aureus, Pseudomonas aeruginosa, Burkholderia contaminans and Escherichia coli strains, while antifungal activity was tested against the Candida species C. albicans, C. glabrata, C. parapsilosis and C. tropicalis. The antimicrobial activity of the complexes ranged from very high (complex 4) to moderate (complex 6) or low (complex 8), depending on the structural and electronic characteristics of the camphorimine ligands. Notably, the highest antibacterial and anti-Candida activities do not coincide in the same complex and in some cases they were even opposite, as is the case of complex 4 which exhibits a high anti-bacterial and low antifungal activity. These distinct results suggest that the complexes may have different mechanisms against prokaryotic and eukaryotic cells. The antifungal activity of the Ag(I) camphorimine complexes (in particular of complex 1) was found to be very high (MIC = 2 μg/mL) against C. parapsilosis, being also registered a prominent activity against C. tropicalis and C. glabrata. None of the tested compounds inhibited C. albicans growth, being this attributed to the ability of these yeast cells to mediate the formation of less toxic Ag nanoparticles, as confirmed by Scanning Electron Microscopy images. The high antibacterial and anti-Candida activities of the here studied camphorimine complexes, especially of complexes 1 and 7, suggests a potential therapeutic application for these compounds.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Ag(I) camphorimine complexes with antimicrobial activity towards clinically important bacteria and species of the Candida genus

et al. 2017

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“… Camphor derivatives of the imine type: Y-aromatic or aliphatic; R 1 = H, Me, Ph; R 2 = H, Me, Ph, among others; Z = phenyl; biphenyl, linear alkane. For preparative details see references (i)—[ 48 ]; (ii)—[ 42 ]; (iii)—[ 49 , 50 ]; (iv)—[ 42 , 51 ]; (v)—[ 42 , 52 ]. …”

Section: Figurementioning

confidence: 99%

Silver Camphor Imine Complexes: Novel Antibacterial Compounds from Old Medicines

et al. 2018

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The emergence of bacterial resistance to available antimicrobials has prompted the search for novel antibacterial compounds to overcome this public health problem. Metal-based complexes have been much less explored than organic compounds as antimicrobials, leading to investigations of the antimicrobial properties of selected complexes in which silver may occupy the frontline due to its use as medicine since ancient times. Like silver, camphor has also long been used for medicinal purposes. However, in both cases, limited information exists concerning the mechanisms of their antimicrobial action. This work reviews the present knowledge of the antimicrobial properties of camphor-derived silver complexes, focusing on recent research on the synthesis and antimicrobial properties of complexes based on silver and camphor imines. Selected examples of the structure and antimicrobial activity relationships of ligands studied so far are presented, showing the potential of silver camphorimine complexes as novel antimicrobials.

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“…The camphorimines were obtained from camphorquinone by reaction with the appropriate amine or hydrazine in ethanol using reported procedures [18,27,28,29]. In the case of air sensitive complexes, Schlenk and vacuum techniques were used.…”

Section: Methodsmentioning

confidence: 99%

Antimicrobial Activity of Silver Camphorimine Complexes against Candida Strains

et al. 2019

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Hydroxide [Ag(OH)L] (L = IVL, VL, VIL, VIIL), oxide [{AgL}2}(μ-O)] (L = IL, IIL, IIIL, VL, VIL) or chloride [AgIIL]Cl, [Ag(VIL)2]Cl complexes were obtained from reactions of mono- or bicamphorimine derivatives with Ag(OAc) or AgCl. The new complexes were characterized by spectroscopic (NMR, FTIR) and elemental analysis. X-ray photoelectron spectroscopy (XPS), ESI mass spectra and conductivity measurements were undertaken to corroborate formulations. The antimicrobial activity of complexes and some ligands were evaluated towards Candida albicans and Candida glabrata, and strains of the bacterial species Escherichia coli, Burkholderia contaminans, Pseudomonas aeruginosa and Staphylococcus aureus based on the Minimum Inhibitory Concentrations (MIC). Complexes displayed very high activity against the Candida species studied with the lowest MIC values (3.9 µg/mL) being observed for complexes 9 and 10A against C. albicans. A significant feature of these redesigned complexes is their ability to sensitize C. albicans, a trait that was not found for the previously investigated [Ag(NO3)L] complexes. The MIC values of the complexes towards bacteria were in the range of those of [Ag(NO3)L] and well above those of the precursors Ag(OAc) or AgCl. The activity of the complexes towards normal fibroblasts V79 was evaluated by the MTT (3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide) assay. Results showed that the complexes have a significant cytotoxicity.

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Insight into the cytotoxicity of polynuclear Cu(I) camphor complexes

Cited by 22 publications

References 24 publications

Ag(I) camphorimine complexes with antimicrobial activity towards clinically important bacteria and species of the Candida genus

Ag(I) camphorimine complexes with antimicrobial activity towards clinically important bacteria and species of the Candida genus

Silver Camphor Imine Complexes: Novel Antibacterial Compounds from Old Medicines

Antimicrobial Activity of Silver Camphorimine Complexes against Candida Strains

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