Trithiocyanurate Complexes of Iron, Manganese and Nickel and Their Anticholinesterase Activity

Kopel, Pavel; Doležal, Karel; Langer, Vratislav; Jun, Daniel; Adam, Vojtěch; Kuča, Kamil; Kizek, René

doi:10.3390/molecules19044338

Cited by 11 publications

(8 citation statements)

References 40 publications

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“…The Schiff base, [(2-[( E )-2-pyridylmethyleneamino]- N -[2-[( E )-2-pyridylmethylene-amino]ethyl]ethanamine)], was prepared according to ref with few modifications. Briefly, 1900 μL of 2-pyridinecarboxaldehyde and 1080 μL of diethylenetriamine were mixed and heated under reflux in methanol (35 mL) for 6 h. After cooling, MeOH was added again to bring the volume to 50 mL to prepare the desired Schiff base solution.…”

Section: Methodsmentioning

confidence: 99%

Real-Time Visualization of Cell Membrane Damage Using Gadolinium–Schiff Base Complex-Doped Quantum Dots

Moulick

Heger

Milosavljević

et al. 2018

ACS Appl. Mater. Interfaces

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Despite the importance of cell membranes for maintenance of integrity of cellular structures, there is still a lack of methods that allow simple real-time visualization of their damage. Herein, we describe gadolinium−Schiff basedoped quantum dots (GdQDs)-based probes for a fast facile spatial labeling of membrane injuries. We found that GdQDs preferentially interact through electron-rich and hydrophobic residues with a specific sequence motif of NHE-RF2 scaffold protein, exposed upon membrane damage. Such interaction results in a fast formation of intensively fluorescent droplets with a higher resolution and in a much shorter time compared to immunofluorescence using organic dye. GdQDs have high stability, brightness, and considerable cytocompatibility, which enable their use in long-term experiments in living cultures. To the best of our knowledge, this is the first report, demonstrating a method allowing real-time monitoring of membrane damage and recovery without any special requirements for instrumentation. Because of intensive brightness and simple signal pattern, GdQDs allow easy examination of interactions between cellular membranes and cell-penetrating peptides or cytostatic drugs. We anticipate that the simple and flexible method will also facilitate the studies dealing with host−pathogen interactions.

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Section: Methodsmentioning

confidence: 99%

Real-Time Visualization of Cell Membrane Damage Using Gadolinium–Schiff Base Complex-Doped Quantum Dots

Moulick

Heger

Milosavljević

et al. 2018

ACS Appl. Mater. Interfaces

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“…The biological roles of metals and their complexes with Mn(II),Co(II), and Ni(II) are of interest because chelation of metals strongly influence the nature and magnitude of pharmacological activities by interacting with active sites of enzymes [21]. Thus, metal chelation is used in many neurobiological and pharmaceutical applications for the treatment of a neurological disease such as AD [20,22]. The metal ions in the current study were studied in order to investigate potential synergism or structural interaction with the carboxylic group of flurbiprofen.…”

Section: Discussionmentioning

confidence: 99%

Tris-diamine-derived transition metal complexes of flurbiprofen as cholinesterase inhibitors

Jamil¹,

Sultana²,

Ashraf³

et al. 2018

Trop. J. Pharm Res

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Purpose:To synthesize novel tris-diamine-derived transition metal complexes of flurbiprofen M(C2H8N2)3 (fp)2 and M(C3H10N2)3 (fp)2, and to evaluate their acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities. Method: Tris-diamine-derived transition metal complexes of Co(II), Ni(II), and Mn(II) were synthesized and characterized using ultraviolet-visible (UV-Vis) spectroscopy, Fourier transform-infrared (FT-IR) spectroscopy, elemental analysis, magnetic susceptibility, conductivity measurement and single crystal x-ray analysis. The synthesized complexes were also evaluated for their AChE and BChE inhibitory activities. Results: Based on magnetic susceptibility and electronic studies, the synthesized complexes possessed distorted octahedral geometry. Conductance measurements indicated that diamine-derived metal complexes of flurbiprofen were electrolytes, whereas, simple metal complexes of flurbiprofen were non-electrolytes. The structure of Ni (C2H8N2)3 (fp)2 was also confirmed by single crystal x-ray analysis. The synthesized metal complexes exhibited moderate-to-very good inhibition of AChE and BChE. In vitro assays revealed that Ni complexes were most active, with the least half-maximal inhibitory concentration (IC50) values against AChE and BChE, compared to Co and Mn complexes. Furthermore,1, complexes were more potent, with lower IC50 values against both AChE and BChE, compared to 1,3-diaminopropane-derived complexes. Among the complexes, 4a and 5a revealed significant cholinesterase inhibitory activities relative to the standard drug, galantamine. Conclusion: All the synthesized metal complexes are active against AChE and BChE, but only 4a and 5a are more active than the standard drug, galantamine, indicating their potential for drug development. This is an Open Access article that uses a funding model which does not charge readers or their institutions for access and distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0) and the Budapest

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“…The Schiff base, [(2-[(E)-2-pyridylmethyleneamino]- N -[2-[(E)-2-pyridylmethylene-amino]ethyl]ethanamine)], was prepared according to [ 45 ] with slight modifications. Briefly, 1080 µL of diethylenetriamine and 1900 µL of 2-pyridinecarboxaldehyde were mixed and heated under reflux in methanol for 6 h. After cooling, methanol was added to make the final volume up to 50 mL to get the desired Schiff base solution.…”

Section: Methodsmentioning

confidence: 99%

Improving cytocompatibility of CdTe quantum dots by Schiff-base-coordinated lanthanides surface doping

et al. 2018

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BackgroundSuitable fluorophores are the core of fluorescence imaging. Among the most exciting, yet controversial, labels are quantum dots (QDs) with their unique optical and chemical properties, but also considerable toxicity. This hinders QDs applicability in living systems. Surface chemistry has a profound impact on biological behavior of QDs. This study describes a two-step synthesis of QDs formed by CdTe core doped with Schiff base ligand for lanthanides [Ln (Yb3+, Tb3+ and Gd3+)] as novel cytocompatible fluorophores.ResultsMicrowave-assisted synthesis resulted in water-soluble nanocrystals with high colloidal and fluorescence stability with quantum yields of 40.9–58.0%. Despite induction of endocytosis and cytoplasm accumulation of Yb- and TbQDs, surface doping resulted in significant enhancement in cytocompatibility when compared to the un-doped CdTe QDs. Furthermore, only negligible antimigratory properties without triggering formation of reactive oxygen species were found, particularly for TbQDs. Ln-doped QDs did not cause observable hemolysis, adsorbed only a low degree of plasma proteins onto their surface and did not possess significant genotoxicity. To validate the applicability of Ln-doped QDs for in vitro visualization of receptor status of living cells, we performed a site-directed conjugation of antibodies towards immuno-labeling of clinically relevant target—human norepinephrine transporter (hNET), over-expressed in neuroendocrine tumors like neuroblastoma. Immuno-performance of modified TbQDs was successfully tested in distinct types of cells varying in hNET expression and also in neuroblastoma cells with hNET expression up-regulated by vorinostat.ConclusionFor the first time we show that Ln-doping of CdTe QDs can significantly alleviate their cytotoxic effects. The obtained results imply great potential of Ln-doped QDs as cytocompatible and stable fluorophores for various bio-labeling applications.

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Trithiocyanurate Complexes of Iron, Manganese and Nickel and Their Anticholinesterase Activity

Cited by 11 publications

References 40 publications

Real-Time Visualization of Cell Membrane Damage Using Gadolinium–Schiff Base Complex-Doped Quantum Dots

Real-Time Visualization of Cell Membrane Damage Using Gadolinium–Schiff Base Complex-Doped Quantum Dots

Tris-diamine-derived transition metal complexes of flurbiprofen as cholinesterase inhibitors

Improving cytocompatibility of CdTe quantum dots by Schiff-base-coordinated lanthanides surface doping

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