Complexes formed by adrenaline and related compounds with transition-metal ions—II complexes with copper(II)

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

doi:10.1016/0022-1902(65)80166-x

Cited by 26 publications

(8 citation statements)

References 20 publications

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“…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: 93%

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: 93%

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 structural formulas are shown in Figure 1. These ligands are written as H 2 LH + , where phenolic protons are written on the left side of L. The catecholamine complexes of many transition metals have been reported in the literature, [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] but information about the interactions of lanthanide(III) and catecholamines is restricted. Wu et al 21 investigated complexes of lanthanum(III) with adrenaline by a potentiometric method and a quantum chemical ab initio method under physiological conditions (335 K and an ionic strength of 0.15 mol‚dm -3 NaCl), to clarify neuroendocrine effects and the underlying mechanism of lanthanides.…”

Section: Introductionmentioning

confidence: 99%

Study on the Interaction of Yttrium(III) with Adrenaline, Noradrenaline, and Dopamine

Aydın

2007

J. Chem. Eng. Data

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Yttrium(III) equilibria in the presence of catecholamines adrenaline (AD), noradrenaline (NAD), and dopamine (DP) have been investigated by potentiometric titration in aqueous solution in I ) 0.20 mol‚dm -3 KCl ionic medium and at 298.15 K. The complexation model for Y(III)-catecholamine systems has been established by the "BEST" software from the potentiometric data. The types of complexes in the yttrium(III)-catecholamine systems have been ascertained, and the protonation constants for catecholamines and the stability constants for yttrium(III) complexes with catecholamines have been obtained. The stability constants of YHL 2+ -and Y(HL) 2 +type complexes are reported. Catecholamines can form stable yttrium(III) complexes with the phenolic hydroxyl groups of catecholamines as the binding site to yttrium(III). In terms of the ligands, the stability of complexes ranks in an order such as dopamine > adrenaline > noradrenaline. The stability constants of Y(III)-adrenaline complexes are higher than their La(III) complexes due to the higher ionic potential of Y(III). The ionic radii of Ca(II) and Y(III) are roughly equal, but Y(III) has a higher charge than Ca(II). Therefore, Y(III)-catecholamine complexes are relatively more stable than Ca(II)-catecholamine complexes. This result may be utilized for in vitro and in vivo studies.

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“…It should also be noted that in studies of complexation of phenolic amines it has commonly been assumed (erroneously, as will be shown below) that the ammonium group is the stronger acid (e.g. [5,6,[9][10][11][12] and references therein).…”

Section: Introductionmentioning

confidence: 99%

Nmr studies of catecholamines. Acid dissociation equilibria in aqueous solutions

Granot

1976

FEBS Letters

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Complexes formed by adrenaline and related compounds with transition-metal ions—II complexes with copper(II)

Cited by 26 publications

References 20 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

Study on the Interaction of Yttrium(III) with Adrenaline, Noradrenaline, and Dopamine

Nmr studies of catecholamines. Acid dissociation equilibria in aqueous solutions

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