Two macrocyclic pentaaza compounds containing pyridine evaluated as novel chelating agents in copper(II) and nickel(II) overload

Fernandes, Ana Sofia; Cabral, M. Fátima; Costa, Judite; Castro, Matilde; Delgado, Rita; Drew, Michael G. B.; Félix, Vı́tor

doi:10.1016/j.jinorgbio.2010.11.014

Cited by 28 publications

(20 citation statements)

References 48 publications

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“…A 10-mM stock solution of DHR was prepared in DMSO, aliquoted, and stored under nitrogen at À20°C. Cu [15]pyN 5 was synthesised by our group as previously described (14).…”

Section: Methodsmentioning

confidence: 99%

“…HUVEC viability was evaluated by the crystal violet assay. HUVECs were seeded in a 96-well A B Figure 1: Chemical structure of the macrocyclic ligand [15]pyN 5 (A) and molecular structure of its copper(II) complex Cu [15]pyN 5 (B) (14).…”

Section: Cell Viability Assaysmentioning

confidence: 99%

“…high pCu value for physiological pH (14). These features are essential to prevent possible losses of activity and toxic effects in biological milieus.…”

mentioning

confidence: 99%

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Role of the Copper(II) Complex Cu[15]pyN₅ in Intracellular ROS and Breast Cancer Cell Motility and Invasion

et al. 2015

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Multiple mechanisms related to metastases undergo redox regulation. Cu[15]pyN5 is a redox-active copper(II) complex previously studied as a chemotherapy sensitizer in mammary cells. The effects of a cotreatment with Cu[15]pyN5 and doxorubicin (dox) were evaluated in two human breast cancer cell lines: MCF7 (low aggressiveness) and MDA-MB-231 (highly aggressive). Cu[15]pyN5 decreased MCF7-directed cell migration. In addition, a cotreatment with dox and Cu[15]pyN5 reduced the proteolytic invasion of MDA-MB-231 cells. Cell detachment was not affected by exposure to these agents. Cu[15]pyN5 and dox significantly increased intracellular ROS in both cell lines. This increase could be at least partially due to H2 O2 accumulation. The combination of Cu[15]pyN5 with dox may be beneficial in breast cancer treatment as it could help reduce cancer cell migration and invasion. Moreover, the ligand [15]pyN5 has a high affinity for copper(II) and displays potential anti-angiogenic properties. Overall, we present a potential drug that might arrest the progression of breast cancer by different and complementary mechanisms.

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“…A 10-mM stock solution of DHR was prepared in DMSO, aliquoted, and stored under nitrogen at À20°C. Cu [15]pyN 5 was synthesised by our group as previously described (14).…”

Section: Methodsmentioning

confidence: 99%

Section: Cell Viability Assaysmentioning

confidence: 99%

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Role of the Copper(II) Complex Cu[15]pyN₅ in Intracellular ROS and Breast Cancer Cell Motility and Invasion

et al. 2015

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“…[8] Polyazamacrocycle has fascinated an extensive significance in current times due to their capability of interacting with both ions like anion and cation and their wide applicability as ion sensors. [9][10][11][12][13][14] The designing, synthesis and evaluation of new drugs that improve the contrast between normal and diseased tissues strongly contributed to the recent developments in this area. The stabilization of unusual oxidation states of the transition metal ion by macrocyclic ligand is very much significant.…”

Section: Introductionmentioning

confidence: 99%

In‐vitro DNA binding and antimicrobial studies of trivalent transition metal ion based macrocyclic complexes

Sangwan

Singh

2019

Vietnam Journal of Chemistry

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In the current research work diaminotoluene based tetra-azamacrocyclic-14 membered [N4] macrocylic complexes of nitrate, chloride and acetate trivalent transition metals salts of Cr(III) and Fe(III) have been synthesized by taking the route of template methodology. The synthesized complexes were fully characterized by spectroscopic and physicoanalytical techniques like IR, ESI-MS, ESR, Powder XRD, TGA, UV-visible, magnetic moment, molar conductance, in addition to the elemental analysis measurements. The monomeric and electrolytic nature of the complexes is elucidated by the help of ESI-MS and molar conductance values that reveals about the 1:2 electrolytic behaviour. On the basis of above analytical techniques the complexes may be empirically formulated as [MLX]X2 in which L is macrocyclic ligand obtained from the [2+2] condensation reaction of 3,4-diaminotoluene (DAT) and dibenzoylmethane (DBM). The thermal data provides an indication towards the absence of water molecular and various decomposition steps in the complexes. Further the compounds were screened for their antimicrobial potency against few strains of bacteria and fungus and fair results were found from the above studies. In addition to these DNA binding activity was also performed in order to elucidate the mode of binding the newly synthesised complexes.

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“…[18][19][20][21][22][23][24][25] Metal complexes derived from tetra-aza macrocyclic ligands generally present large stability constants, on the order of log K ≥ 20.0 in the case of copper(II) complexes. 17,18,[26][27][28][29][30][31][32] In a 1969 paper by Margerum and Cabbiness, the copper(II) complex derived from a tetra-aza macrocycle was determined to be 10 4 times more stable than the non-cyclic tetraamine ligand. 16 The cyclic nature of the ligand backbone leads to an increase in the kinetic and thermodynamic stability of a given metal-ion complex in solution, which is in a magnitude greater than that of the chelate effect.…”

Section: Introductionmentioning

confidence: 99%

Chemical characteristics of the products of the complexation reaction between copper(II) and a tetra-aza macrocycle in the presence of chloride ions

Lincoln

Arroyo‐Currás

Johnston

et al. 2015

Journal of Coordination Chemistry

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The reaction of copper(II) perchlorate with the hydrochloride salt of 3, 6,9,15-tetraazabicyclo[9.3.1]penta-deca-1,11,13-triene (L1) in acetonitrile forms two macrocyclic complexes that can be characterized; [L1Cu II Cl][ClO 4 ] (1) and [L1Cu II Cl] 2 [CuCl 4 ] (2). The structural, electronic and redox properties of these complexes were studied using spectroscopy (EPR and UV-visible), and electrochemistry. In addition the solid state structure of 1 was obtained using X-ray diffraction. The copper(II) is five-coordinate; ligated by four N-atoms of the macrocycle and a chloride atom. EPR studies of 1 both DMF and aqueous solution indicate the presence of a single copper(II) species. In contrast, EPR studies of 2 performed in frozen DMF and in the solid-state reveal the presence of two spectroscopically distinct copper(II) complexes assigned as [L1Cu II Cl] + and [Cu II Cl 4 ] 2-. Lastly, electrochemical studies demonstrate that both [L1Cu II Cl] + and [Cu II Cl 4 ] 2-are redox active. Specifically, the [L1Cu II Cl] + undergoes a quasi-reversible Cu(II)/(I) redox reaction in the absence of excess chloride.In the presence of chloride, however, the chemical irreversibility of this couple becomes evident at concentrations of chloride that exceed 50 mM. As a result, the presence of chloride from the chemical equilibrium of this latter species impedes the reversibility of the reduction of [L1Cu II Cl] + to [L1Cu I Cl] 0 .

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Two macrocyclic pentaaza compounds containing pyridine evaluated as novel chelating agents in copper(II) and nickel(II) overload

Cited by 28 publications

References 48 publications

Role of the Copper(II) Complex Cu[15]pyN₅ in Intracellular ROS and Breast Cancer Cell Motility and Invasion

Role of the Copper(II) Complex Cu[15]pyN₅ in Intracellular ROS and Breast Cancer Cell Motility and Invasion

In‐vitro DNA binding and antimicrobial studies of trivalent transition metal ion based macrocyclic complexes

Chemical characteristics of the products of the complexation reaction between copper(II) and a tetra-aza macrocycle in the presence of chloride ions

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Two macrocyclic pentaaza compounds containing pyridine evaluated as novel chelating agents in copper(II) and nickel(II) overload

Cited by 28 publications

References 48 publications

Role of the Copper(II) Complex Cu[15]pyN5 in Intracellular ROS and Breast Cancer Cell Motility and Invasion

Role of the Copper(II) Complex Cu[15]pyN5 in Intracellular ROS and Breast Cancer Cell Motility and Invasion

In‐vitro DNA binding and antimicrobial studies of trivalent transition metal ion based macrocyclic complexes

Chemical characteristics of the products of the complexation reaction between copper(II) and a tetra-aza macrocycle in the presence of chloride ions

Contact Info

Product

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Role of the Copper(II) Complex Cu[15]pyN₅ in Intracellular ROS and Breast Cancer Cell Motility and Invasion

Role of the Copper(II) Complex Cu[15]pyN₅ in Intracellular ROS and Breast Cancer Cell Motility and Invasion