Ternary copper(II) complex of 5-hydroxytryptophan and 1,10-phenanthroline with several pharmacological properties and an adequate safety profile

Naso, Luciana G.; Medina, Juan José Martínez; D’Alessandro, Francesco; Rey, Marilin; Rizzi, Alberto Claudio; Piro, Oscar E.; Echeverría, Gustavo A.; Ferrer, Evelina G.; Williams, Patricia Ana María

doi:10.1016/j.jinorgbio.2019.110933

Cited by 17 publications

(15 citation statements)

References 54 publications

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“…On the other hand, we previously designed Cu (II) and Zn (II) ternary complexes based on phen and with other ligands like 5‐hydroxytryptophan (5‐HTP), 58 coumarin‐3‐carboxylate (CCA), 59 or methimazole (Met) 60 . The ternary Cu/phen/5‐HTP and Zn/phen/CCA complexes were not active against P .…”

Section: Resultsmentioning

confidence: 99%

“…The copper complex has a slightly lower activity against E. coli ATCC 35218 and C. tropicalis but has slightly higher activity against S. aureus ATCC 25923 and E. faecalis ATCC 29212 than the others complexes. Taken from Tévez et al 54 On the other hand, we previously designed Cu (II) and Zn (II) ternary complexes based on phen and with other ligands like 5-hydroxytryptophan (5-HTP), 58 coumarin-3-carboxylate (CCA), 59 or methimazole (Met). 60 The ternary Cu/phen/5-HTP and Zn/phen/CCA complexes were not active against P. aeruginosa (MIC> 1500 μg ml À1 ), whereas the ternary Cu/phen/Met displayed a MIC value of 375 μg ml À1 against this pathogen.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

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Computational studies, antimicrobial activity, inhibition of biofilm production, and safety profile of the cadmium complex of 1,10‐phenanthroline and cyanoguanidine

Falkievich

Medina

Alegre

et al. 2022

Applied Organom Chemis

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We have previously determined the crystal structure of the metal complex [Cd (1,10-phenanthroline) 2 (SO 4 )H 2 O]cyanoguanidine•5H 2 O that was characterized by spectroscopic measurements. The antibacterial activity was also determined by the agar diffusion test (zones of inhibition). In the present work, calculations based on density functional theory were performed to determine the contributions of the two different tautomers of cyanoguanidine to the vibrational IR and Raman experimental spectra. Moreover, the antimicrobial (antibacterial and antifungal) activity of the complex and cadmium ion was assessed and the minimum inhibitory concentration (MIC) was determined.The complexation increased the antimicrobial activity against Pseudomonas aeruginosaATCC 27853 and inhibited the biofilm production of this pathogen.Antimicrobial studies were coupled with the evaluation of safety, using the Artemia salinaand Ames test. At the concentrations tested, the cadmium complex behaved as a non-mutagenic and non-toxic compound. Therefore, the interaction of cadmium (II) with N and O-containing ligands may provide a promising strategy for the development of novel and safe drugs with antimicrobial activity.

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Section: Resultsmentioning

confidence: 99%

Section: Antimicrobial Activitymentioning

confidence: 99%

Computational studies, antimicrobial activity, inhibition of biofilm production, and safety profile of the cadmium complex of 1,10‐phenanthroline and cyanoguanidine

Falkievich

Medina

Alegre

et al. 2022

Applied Organom Chemis

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“…MMPs are a family of Zn 2 - and Ca 2 -dependent enzymes, and PHEN may inactivate MMPs by chelating Zn 2 with two N atoms. 12 , 28 Furthermore, PHEN is a small-molecule 29 (molecular weight: 180.205) metal chelator; 30 , 31 thus, PHEN may remain in dentin and function regardless of the condition in which it was applied. Pertinently, catK is a cysteine proteinase, containing a thiol group (-SH).…”

Section: Discussionmentioning

confidence: 99%

Do matrix metalloproteinase and cathepsin K inhibitors work synergistically to reduce dentin erosion?

et al. 2023

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Objectives To evaluate the effects of matrix metalloproteinase (MMP) and cathepsin K (catK) inhibitors on resistance to dentin erosion. Methodology A total of 96 dentin specimens (3×3×2 mm) were prepared and randomly assigned into four groups (n=24): deionized water (DW); 1 µM odanacatib (ODN, catK inhibitor); 1 mM 1,10-phenanthroline (PHEN, MMP inhibitor); and 1 µM odanacatib + 1 mM 1,10-phenanthroline (COM). Each group was further divided into two subgroups for the application of treatment solutions before (PRE) and after erosive challenges (POST). All specimens were subjected to four daily erosive challenges for 5 d. For each erosive challenge, the specimens in subgroup PRE were immersed in the respective solutions before cola drinks, while the specimens in subgroup POST were immersed in the respective solutions after cola drinks (the immersion duration was 5 min in both cases). All specimens were stored in artificial saliva at 37°C between erosive challenges. The erosive dentin loss (EDL) was measured by profilometry. The residual demineralized organic matrix (DOM) of specimens was removed using type VII collagenase and evaluated by profilometry. Both the EDL and thickness of the residual DOM were statistically analyzed by two-way analysis of variance (ANOVA) and Bonferroni’s test (α=0.05). The surface topography and transverse sections of the specimens were observed using SEM. MMPs and catK were immunolabeled in the eroded dentin and in situ zymography was performed to evaluate the enzyme activity. Results Significantly lower EDL was found in the groups ODN, PHEN, and COM than in the control group (all p<0.05), while no significant difference in EDL was found among the groups ODN, PHEN, and COM (all p>0.05). The application sequence showed no significant effect on the EDL of the tested groups (p=0.310). A significantly thicker DOM was observed in the group ODN than in the control group regardless of the application sequence (both p<0.05). The treatment with ODN, PHEN, and COM inhibited the gelatinolytic activity by approximately 46.32%, 58.6%, and 74.56%, respectively. Conclusions The inhibition of endogenous dentinal MMPs and catK increases the acid resistance of human dentin but without an apparent synergistic effect. The inhibition of MMPs and catK is equally effective either before or after the acid challenge.

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“…The authors demonstrated how the anticancer activity of this compound is exerted through cellular ROS production, GSH depletion and alteration of mitochondrial potential. The complex shows also antimetastatic activity on A-549 cells with inhibition of cells adhesion, migration, and invasion [ 51 ].…”

Section: Mixed Cu(ii) Phen-based Complexesmentioning

confidence: 99%

Copper(II) Phenanthroline-Based Complexes as Potential AntiCancer Drugs: A Walkthrough on the Mechanisms of Action

et al. 2021

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Copper is an endogenous metal ion that has been studied to prepare a new antitumoral agent with less side-effects. Copper is involved as a cofactor in several enzymes, in ROS production, in the promotion of tumor progression, metastasis, and angiogenesis, and has been found at high levels in serum and tissues of several types of human cancers. Under these circumstances, two strategies are commonly followed in the development of novel anticancer Copper-based drugs: the sequestration of free Copper ions and the synthesis of Copper complexes that trigger cell death. The latter strategy has been followed in the last 40 years and many reviews have covered the anticancer properties of a broad spectrum of Copper complexes, showing that the activity of these compounds is often multi factored. In this work, we would like to focus on the anticancer properties of mixed Cu(II) complexes bearing substituted or unsubstituted 1,10-phenanthroline based ligands and different classes of inorganic and organic auxiliary ligands. For each metal complex, information regarding the tested cell lines and the mechanistic studies will be reported and discussed. The exerted action mechanisms were presented according to the auxiliary ligand/s, the metallic centers, and the increasing complexity of the compound structures.

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Ternary copper(II) complex of 5-hydroxytryptophan and 1,10-phenanthroline with several pharmacological properties and an adequate safety profile

Cited by 17 publications

References 54 publications

Computational studies, antimicrobial activity, inhibition of biofilm production, and safety profile of the cadmium complex of 1,10‐phenanthroline and cyanoguanidine

Computational studies, antimicrobial activity, inhibition of biofilm production, and safety profile of the cadmium complex of 1,10‐phenanthroline and cyanoguanidine

Do matrix metalloproteinase and cathepsin K inhibitors work synergistically to reduce dentin erosion?

Copper(II) Phenanthroline-Based Complexes as Potential AntiCancer Drugs: A Walkthrough on the Mechanisms of Action

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