Metal complexes of a dipyridine octaazamacrocycle: stability constants, structural and modelling studies

Cruz, Carla; Carvalho, Sílvia; Delgado, Rita; Drew, Michael G. B.; Félix, Vı́tor; Goodfellow, Brian J.

doi:10.1039/b304381a

Cited by 11 publications

(13 citation statements)

References 30 publications

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“…Compounds Me 2 [28]py 2 N 6 , [32]phen 2 N 4 and [30]phen 2 N 6 have been prepared as recently described in [27] , [28] . Compound [16]phenN 2 is a versatile precursor for the assembly of macropolycyclic cryptphen, since it contains two secondary amine groups that can be connected by 2∶2 cyclizations with 1,0-phenanthroline moieties.…”

Section: Resultsmentioning

confidence: 99%

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Targeting of Mitochondria-Endoplasmic Reticulum by Fluorescent Macrocyclic Compounds

et al. 2011

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BackgroundUseful probes of the intracellular environment that target a specific organelle in order to allow direct observation of the changes in these regions is of high current interest. Macrocyclic ligands have already revealed themselves as important selective hosts in some biological applications, forming stable and specific complexes. Therefore, in this paper, several macrocyclic ligands are evaluated as potential molecular probes.MethodologyFour polyammonium macrocycles and one macrotricyclic bearing pyridine and phenanthroline chromophores have been synthesised and evaluated as molecular probes. The cytotoxicity of the compounds has been analyzed using human breast cancer cells (MCF-7), non-cancerous human dermal fibroblasts (NHDF) and human adult dermal skin fibroblasts from a breast cancer patient (P14). All the compounds showed low toxicity at concentrations ranging from 10 nM to 10 µM, except for [32]phen2N4 which proved to be highly cytotoxic for MCF-7 cells. Flow cytometry studies evidenced that the percentage of apoptotic and necrotic MCF-7 and NHDF cells induced by the compounds is considerably low. Also, flow cytometry analysis showed that some compounds seem to modify the mitochondrial membrane potential (MMP) of the cells. Fluorescence microscopy evidenced that compounds easily cross the plasma membrane (5 min) and accumulated into the mitochondria, as confirmed by co-localization with MitoTracker Green™. The fluorescence images also evidenced an intact mitochondria structure after 48 h. Moreover, reticular staining suggestive of endoplasmic reticulum (ER) localization, in addition to the mitochondrial one, has been found by confocal microscopy.ConclusionOur study reveals that compounds Me2[28]py2N6, cryptphen, [16]phenN2, [30]phen2N6, have low toxicity and localize in mitochondria and ER. The ability of these compounds for translocating the cellular membrane (5 min) without special conditioning of the cells or derivatization of the probe, the time-dependent localization (48 h) and the cellular viability provide a proof-of-concept towards their use as promising probes towards biomedical studies.

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Section: Resultsmentioning

confidence: 99%

“…1,10-phenanthroline-2,9 dicarboxaldehyde and 2,9-bis(bromomethyl)-1,10-phenanthroline were prepared as previously described in [35] . The synthesis of the compounds Me 2 [28]py 2 N 6 , [32]phen 2 N 4 and [30]phen 2 N 6 was also described previously [27] , [28] .…”

Section: Methodsmentioning

confidence: 99%

Targeting of Mitochondria-Endoplasmic Reticulum by Fluorescent Macrocyclic Compounds

et al. 2011

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“…The most significant change has been observed on changing the ring size of the ligand (Autzen et al, 2003;Cruz et al, 2003). Macrocycles with a large cavity, which can accommodate two metal ions, can be used to bind the metal center at fixed distances.…”

Section: Introductionmentioning

confidence: 97%

Synthesis, Electrochemistry and Spectral Studies on Cobalt(II) and Manganese (II) Complexes with 12-,14-,15-, and 18-membered N4, N2O2, N2O2S, N6 Donor Macrocyclic Ligands

Chandra¹,

Kumar²

2005

LSRT

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donor macrocyclic ligands and their complexes with cobalt(II) and manganese(II) of the general composition ML,(NCS) 2 (where M 5 cobalt(II) and manganese(II) and ligands L 5 L 1 , L 2 , L 3 , and L 4 have been synthesized. All of the macrocyclic ligands and their complexes have been characterized by elemental analyses, IR, mass, 1 H NMR, magnetic moments, electronic and EPR spectral studies. The structures of the complexes and the various coordinating groups such as >C5 5N, >CONH, Ph2 2O2 2CH 2 2 2 and >NH are discussed. The redox properties of the complexes were examined by cyclic voltammetery. They exhibit a high potential Co(III)/Co(II) couple along with ligand reduction.

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“…This indicates that there is an octahedral geometry around the Co(II) ion. Various ligand field parameters Dq (943 cm −1 , (0.82)) are calculated using the following equations:37 …”

Section: Resultsmentioning

confidence: 99%

Polymer complexes: LIX. Supramolecular structural, spectral and thermal analysis of N‐[2‐(6‐aminopyridino)] acrylamide polymer complexes

El‐Sonbati

Diab

Mohamed

2011

Polymer International

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Novel ligand N‐[2‐(6‐aminopyridino)] acrylamide (APA) is prepared via amidation of 2,6‐diaminopyridine with acryloyl chloride in dry benzene as solvent. The ligand is characterized on the basis of elemental analysis, infra‐red (IR) analysis and 1H nuclear magnetic resonance. Metal–polymer complexes are reported and characterized based on elemental analysis, molar conductance, magnetic susceptibility measurements, IR, 1H nuclear magnetic resonance, electronic spectra and thermal analysis. The molar conductance of the polymer complexes in dimethylformamide corresponds to a 1:1/1:2 electrolyte, which is non‐electrolytic. IR spectra show that polyAPA is coordinated to the metal ions in a uni‐negatively bidentate manner with N, O donor sites of azomethine N and deprotonated enolic‐O. All the polymer complexes are of high spin type. On the basis of spectral studies an octahedral geometry may be assigned for Co(II) and Ni(II) polymer complexes. The thermal stabilities of the polymer complexes were studied and the activation energies of the degradation were calculated. Copyright © 2011 Society of Chemical Industry

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Metal complexes of a dipyridine octaazamacrocycle: stability constants, structural and modelling studies

Cited by 11 publications

References 30 publications

Targeting of Mitochondria-Endoplasmic Reticulum by Fluorescent Macrocyclic Compounds

Targeting of Mitochondria-Endoplasmic Reticulum by Fluorescent Macrocyclic Compounds

Synthesis, Electrochemistry and Spectral Studies on Cobalt(II) and Manganese (II) Complexes with 12-,14-,15-, and 18-membered N4, N2O2, N2O2S, N6 Donor Macrocyclic Ligands

Polymer complexes: LIX. Supramolecular structural, spectral and thermal analysis of N‐[2‐(6‐aminopyridino)] acrylamide polymer complexes

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