ATR-FTIR spectroscopic investigation of the cis- and trans- bis-( α -amino acids) copper(II) complexes

Berestova, T. V.; Kuzina, L. G.; Amineva, N. A.; Faizrakhmanov, I. S.; Massalimov, I. A.; Мустафин, А. Г.

doi:10.1016/j.molstruc.2017.02.023

Cited by 36 publications

(31 citation statements)

References 34 publications

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“…In fact, crystals of Cu(II)-valine complex were isolated from the supernatant after 2 weeks, and the corresponding FTIR spectrum is reported in Figure S1. This FTIR spectrum, as well as that of Cu-Arg complex (synthetized as described in the experimental section), are in accordance to those reported in the literature [17,25].…”

Section: Resultssupporting

confidence: 90%

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Interaction between Copper Oxide Nanoparticles and Amino Acids: Influence on the Antibacterial Activity

et al. 2019

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The increasing concern about antibiotic-resistance has led to the search for alternative antimicrobial agents. In this effort, different metal oxide nanomaterials are currently under investigation, in order to assess their effectiveness, safety and mode of action. This study focused on CuO nanoparticles (CuO NPs) and was aimed at evaluating how the properties and the antimicrobial activity of these nanomaterials may be affected by the interaction with ligands present in biological and environmental media. Ligands can attach to the surface of particles and/or contribute to their dissolution through ligand-assisted ion release and the formation of complexes with copper ions. Eight natural amino acids (L-Arg, L-Asp, L-Glu, L-Cys, L-Val, L-Leu, L-Phe, L-Tyr) were chosen as model molecules to investigate these interactions and the toxicity of the obtained materials against the Gram-positive bacterium Staphylococcus epidermidis ATCC 35984. A different behavior from pristine CuO NPs was observed, depending on the aminoacidic side chain. These results were supported by physico-chemical and colloidal characterization carried out by means of Fourier-Transform Infrared spectroscopy (FTIR), Differential Scanning Calorimetry (DSC) and Thermo-Gravimetric Analysis (TGA), Inductively Coupled Plasma Mass Spectrometry (ICP-MS) and light scattering techniques (Dynamic Light Scattering (DLS), Electrophoretic Light Scattering (ELS) and Centrifugal Separation Analysis (CSA).

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Section: Resultssupporting

confidence: 90%

“…In the case of Cu-amino acid complexes, the ICP-MS results showed for all the amino acids the formation of Cu(II) complexes with an average stoichiometry of 1:2 (copper:amino acid), as reported in the literature for these complexes [17,18,25,27].…”

Section: Resultssupporting

confidence: 75%

Interaction between Copper Oxide Nanoparticles and Amino Acids: Influence on the Antibacterial Activity

et al. 2019

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“…The asymmetric stretching vibrations of carboxylate, ν as (COO − ) corresponds to the high-intensity band with a frequency of 1602 cm −1 for 1a / 1b and 1627 cm −1 for 2a / 2b . The medium-high intensity band with a frequency of 1394 cm −1 for 1a / 1b and 1411 cm −1 for 2a / 2b ( Supplementary Table S1 ) can be assigned to the symmetric stretching vibrations of carboxylate, ν s (COO − ) [ 12 , 30 ]. The vibration frequency (Δν) which represents the difference between the ν as (COO − ) and the ν s (COO − ) is greater than 200 cm −1 for 1a / 1b and 2a / 2b , highlighting the coordination of the deprotonated carboxyl groups, which belongs to the Schiff base, to vanadium atom in a monodentate manner [ 12 , 31 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, and In Vitro Insulin-Mimetic Activity Evaluation of Valine Schiff Base Coordination Compounds of Oxidovanadium(V)

et al. 2021

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Type 2 diabetes became an alarming global health issue since the existing drugs do not prevent its progression. Herein, we aimed to synthesize and characterize a family of oxidovanadium(V) complexes with Schiff base ligands derived from L-/D-valine (val) and salicylaldehyde (sal) or o-vanillin (van) as insulin-mimetic agents and to assess their potential anti-diabetic properties. Two new oxidovanadium(V) complexes, [{VVO(R-salval)(H2O)}(μ2-O){VVO(R-salval)}] and [{VVO(R-vanval)(CH3OH)}2(μ2-O)], and their S-enantiomers were synthesized and characterized. The compounds exhibit optical activity as shown by crystallographic and spectroscopic data. The stability, the capacity to bind bovine serum albumin (BSA), the cytotoxicity against human hepatoma cell line, as well as the potential anti-diabetic activity of the four compounds are investigated. The synthesized compounds are stable for up to three hours in physiological conditions and exhibit a high capacity of binding to BSA. Furthermore, the synthesized compounds display cytocompatibility at biologically relevant concentrations, exert anti-diabetic potential and insulin-mimetic activities by inhibiting the α-amylase and protein tyrosine phosphatase activity, and a long-term increase of insulin receptor phosphorylation compared to the insulin hormone. Thus, the in vitro anti-diabetic potential and insulin-mimetic properties of the newly synthesized oxidovanadium(V) compounds, correlated with their cytocompatibility, make them promising candidates for further investigation as anti-diabetic drugs.

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“…Infrared (IR) analysis showed the decrease of the stretching absorption at 1700 cm − 1 for C=O and 1200 cm − 1 for C-N (Spreckelmeyer et al 2017 ), indicating that both COO and pyridyl moieties bind to the metal. In attempting to interpret the coordination geometry, we considered both the relative frequency and intensities of both asymmetric (ν as , ~ 1600 cm − 1 ) and symmetric (ν s , ~ 1400 cm − 1 ) COO stretching vibrations for the free and bound chelates (Berestova et al 2017 ). For the DOTA-1Py and -2Py chelates, we observed the evolution of dual maxima upon metal binding, suggesting there exist multiple binding configurations for the COO moieties around the metal.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of DOTA-pyridine chelates for 64Cu coordination and radiolabeling of αMSH peptide

Yang

Gao

McNeil

et al. 2021

EJNMMI radiopharm. chem.

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Background 64Cu is one of the few radioisotopes that can be used for both imaging and therapy, enabling theranostics with identical chemical composition. Development of stable chelators is essential to harness the potential of this isotope, challenged by the presence of endogenous copper chelators. Pyridyl type chelators show good coordination ability with copper, prompting the present study of a series of chelates DOTA-xPy (x = 1–4) that sequentially substitute carboxyl moieties with pyridyl moieties on a DOTA backbone. Results We found that the presence of pyridyl groups significantly increases 64Cu labeling conversion yield, with DOTA-2Py, −3Py and -4Py quantitatively complexing 64Cu at room temperature within 5 min (1 × 10− 4 M). [64Cu]Cu-DOTA-xPy (x = 2–4) exhibited good stability in human serum up to 24 h. When challenged with 1000 eq. of NOTA, no transmetallation was observed for all three 64Cu complexes. DOTA-xPy (x = 1–3) were conjugated to a cyclized α-melanocyte-stimulating hormone (αMSH) peptide by using one of the pendant carboxyl groups as a bifunctional handle. [64Cu]Cu-DOTA-xPy-αMSH retained good serum stability (> 96% in 24 h) and showed high binding affinity (Ki = 2.1–3.7 nM) towards the melanocortin 1 receptor. Conclusion DOTA-xPy (x = 1–3) are promising chelators for 64Cu. Further in vivo evaluation is necessary to assess the full potential of these chelators as a tool to enable further theranostic radiopharmaceutical development.

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ATR-FTIR spectroscopic investigation of the cis- and trans- bis-( α -amino acids) copper(II) complexes

Cited by 36 publications

References 34 publications

Interaction between Copper Oxide Nanoparticles and Amino Acids: Influence on the Antibacterial Activity

Interaction between Copper Oxide Nanoparticles and Amino Acids: Influence on the Antibacterial Activity

Synthesis, Characterization, and In Vitro Insulin-Mimetic Activity Evaluation of Valine Schiff Base Coordination Compounds of Oxidovanadium(V)

Synthesis of DOTA-pyridine chelates for 64Cu coordination and radiolabeling of αMSH peptide

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