Complexes formed by adrenaline and related compounds with transition-metal ions—III

Jameson, R. F.; Neillie, W.F.S.

doi:10.1016/0022-1902(66)80392-5

Cited by 29 publications

(10 citation statements)

References 12 publications

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“…The literature has essentially been with regard to the interaction of epinephrine with divalent metal cations (Mn 2+ , Co 2+ , Ni 2+ , Zn 2+ , Cu 2+ , Cd 2+ , Pb 2+ , Hg 2+ ), even if some data are also available for lanthanide complexes. [65] In a comparison between the speciation models and the stability constants reported in Table 10, a fairly good agreement in terms of simplicity of the speciation schemes (characterized by simple mononuclear species) can be observed. The behavior of the UO 2 2+ /Eph − system has been different in terms of formation of binuclear species with stoichiometry: M 2 L 2 and M 2 L 2 (OH) 2 , as is usual for the chemistry of UO 2 2+ .…”

Section: Literature Comparisonsmentioning

confidence: 59%

“…Taking into account the order of magnitude of the stability of complexes formed by epinephrine with the cations here investigated and comparing it to information from the literature, it is possible to hypothesize that for our systems as well, the interaction should occur via the phenolic oxygen(s) of the two phenolic groups, excluding the amine group of the lateral chain [13,[65][66][67][69][70][71]. There has been various evidence that has supported this assumption, as has been reported by Moustafa [71], who carried out FT-IR spectra on an Hg 2+ /Eph − complex.…”

Section: Literature Comparisonsmentioning

confidence: 94%

“…This is a further indication that only two phenolic groups are involved in coordinating with metal ions. Besides, Jameson and Neille [65] have stated that Ni 2+ /Eph − complexes have anomalous behavior, explaining that there is chelation through the interaction of the phenolic and secondary amine groups, even if it occurs only at given metal-to-ligand molar ratios.…”

Section: Literature Comparisonsmentioning

confidence: 99%

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Understanding the Solution Behavior of Epinephrine in the Presence of Toxic Cations: A Thermodynamic Investigation in Different Experimental Conditions

et al. 2020

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The interactions of epinephrine ((R)-(−)-3,4-dihydroxy-α-(methylaminomethyl)benzyl alcohol; Eph−) with different toxic cations (methylmercury(II): CH3Hg+; dimethyltin(IV): (CH3)2Sn2+; dioxouranium(VI): UO22+) were studied in NaClaq at different ionic strengths and at T = 298.15 K (T = 310.15 K for (CH3)2Sn2+). The enthalpy changes for the protonation of epinephrine and its complex formation with UO22+ were also determined using isoperibolic titration calorimetry: ΔHHL = −39 ± 1 kJ mol−1, ΔHH2L = −67 ± 1 kJ mol−1 (overall reaction), ΔHML = −26 ± 4 kJ mol−1, and ΔHM2L2(OH)2 = 39 ± 2 kJ mol−1. The results were that UO22+ complexation by Eph− was an entropy-driven process. The dependence on the ionic strength of protonation and the complex formation constants was modeled using the extended Debye–Hückel, specific ion interaction theory (SIT), and Pitzer approaches. The sequestering ability of adrenaline toward the investigated cations was evaluated using the calculation of pL0.5 parameters. The sequestering ability trend resulted in the following: UO22+ >> (CH3)2Sn2+ > CH3Hg+. For example, at I = 0.15 mol dm−3 and pH = 7.4 (pH = 9.5 for CH3Hg+), pL0.5 = 7.68, 5.64, and 2.40 for UO22+, (CH3)2Sn2+, and CH3Hg+, respectively. Here, the pH is with respect to ionic strength in terms of sequestration.

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Section: Literature Comparisonsmentioning

confidence: 59%

Section: Literature Comparisonsmentioning

confidence: 94%

Section: Literature Comparisonsmentioning

confidence: 99%

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Understanding the Solution Behavior of Epinephrine in the Presence of Toxic Cations: A Thermodynamic Investigation in Different Experimental Conditions

et al. 2020

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Section: Introductionmentioning

confidence: 99%

“…The literature on adrenaline and its derivative adducts is extensive [6][7][8][9][10][11][12][13][14][15]. The complexes of the first-row transition-metal adrenaline complexes were formed, and the stabilities were discussed [6]. The chemical structures of the complexes of adrenaline and related compounds with Ni 2+ , Cu 2+ , Zn 2+ , Cd 2+ and Pb 2+ were studied using spectroscopic and physicochemical analyses [7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectroscopic, and Biological Assessments on Some New Rare Earth Metal Adrenaline Adducts

et al. 2021

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Adrenaline (Adr) reacts with chlorides of Y3+, Ce3+, Nd3+ and Sm3+ in methanol at 60 °C to yield metal ion adducts of definite composition. These compounds are characterized by elemental analyses, molar conductivity, UV-Vis., 1H–NMR, Raman laser, scanning electron microscopy, energy-dispersive X-ray spectroscopy (EDX), and mid infrared spectral measurement investigations. The adducts are found to have the formulae [Y2(Adr)2(H2O)8]Cl3.8H2O, [Ce(Adr)2(H2O)2]Cl3.10H2O, [Nd(Adr)2(H2O)2]Cl3.6H2O, and [Sm(Adr)2(H2O)2]Cl3.12H2O, respectively. The two phenolic groups of the catechol moiety are linked to central metal ions based on the infrared and Raman laser spectra. The new compounds were tested against five gram-positive and two-gram negative bacteria, in addition to two Aspergillus strains. Metal adducts were shown to have stronger antibacterial and antifungal properties than free adrenaline compounds.

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Antioxidant Properties of Adrenaline in the Presence of Ge‐132

et al. 2019

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Using cyclic voltammetry, UV and 1H NMR spectroscopy, we have investigated the effect of 2‐carboxyethylgermanium (Ge‐132), the most common germanium‐containing dietary supplement, on the antioxidant activity of adrenaline in aqueous solutions. The complex formed by adrenaline and Ge‐132 is oxidizable at 400 mV more positive potentials compared to non‐coordinated adrenaline which corresponds to its 9 kcal/mol more difficult oxidation. An equilibrium constant of the complex formation was estimated (1300 m–1). It was shown that at the concentrations <10–3 m the complex Ge‐132‐adrenaline is mostly dissociated to the initial compounds, and the influence of Ge‐132 on the antioxidant properties of adrenaline becomes significant only when the former is in excess. Considering that such concentrations are typical for physiological conditions, this fact can be significant in identifying the mechanism of the biological action of Ge‐132 and its interference with the biological catechols.

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Complexes formed by adrenaline and related compounds with transition-metal ions—III

Cited by 29 publications

References 12 publications

Understanding the Solution Behavior of Epinephrine in the Presence of Toxic Cations: A Thermodynamic Investigation in Different Experimental Conditions

Understanding the Solution Behavior of Epinephrine in the Presence of Toxic Cations: A Thermodynamic Investigation in Different Experimental Conditions

Synthesis, Spectroscopic, and Biological Assessments on Some New Rare Earth Metal Adrenaline Adducts

Antioxidant Properties of Adrenaline in the Presence of Ge‐132

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