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

The interactions of epinephrine ((R)-(−)-3,4-dihydroxy-α-(methylaminomethyl)benzyl alcohol; Eph(−)) with different toxic cations (methylmercury(II): CH(3)Hg(+); dimethyltin(IV): (CH(3))(2)Sn(2+); dioxouranium(VI): UO(2)(2+)) were studied in NaCl(aq) at different ionic strengths and at T = 298.15 K (T = 310.15 K for (CH(3))(2)Sn(2+)). The enthalpy changes for the protonation of epinephrine and its complex formation with UO(2)(2+) were also determined using isoperibolic titration calorimetry: ΔH(HL) = −39 ± 1 kJ mol(−1), ΔH(H2L) = −67 ± 1 kJ mol(−1) (overall reaction), ΔH(ML) = −26 ± 4 kJ mol(−1), and ΔH(M2L2(OH)2) = 39 ± 2 kJ mol(−1). The results were that UO(2)(2+) 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 pL(0.5) parameters. The sequestering ability trend resulted in the following: UO(2)(2+) >> (CH(3))(2)Sn(2+) > CH(3)Hg(+). For example, at I = 0.15 mol dm(−3) and pH = 7.4 (pH = 9.5 for CH(3)Hg(+)), pL(0.5) = 7.68, 5.64, and 2.40 for UO(2)(2+), (CH(3))(2)Sn(2+), and CH(3)Hg(+), respectively. Here, the pH is with respect to ionic strength in terms of sequestration.