Deciphering the Impact of Nucleosides and Nucleotides on Copper Ion and Dopamine Coordination Dynamics
Abstract
:1. Introduction
2. Results and Discussion
2.1. Interactions in the Cu(II)/DA Binary System
Quantum-Chemical Calculations in the Binary Cu(II)/DA System
2.2. Interactions in the Cu(II)/DA/Nucleoside (or Nucleotide) Ternary System
2.2.1. Molecular Complexes ML′-L
2.2.2. ML′H2L Type Complexes
2.2.3. ML′HL Type Complexes
2.2.4. ML′L and ML′L(OH)x Type Complex
3. Materials and Methods
3.1. Chemicals
3.2. Potentiometric Studies
3.3. Spectroscopic Measurements
3.3.1. VIS Spectroscopy
3.3.2. EPR Spectroscopy
3.3.3. IR Spectroscopy
3.3.4. NMR Spectroscopy
3.4. Quantum-Chemical Calculations
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Systems | Species | logβ | logKe | Ref. |
---|---|---|---|---|
DA | H3(DA)3+ | 32.20 ± 0.07 | 8.82 | 32.40 [32], 31.71 [39], 31.79 [31] |
H2(DA)2+ | 23.38 ± 0.06 | - | 23.51 [32], 22.65 [39], 22.94 [31] | |
H(DA)+ | not determined | - | ||
Cu(II)/DA | CuH(DA)3+ | 23.93 ± 0.01 | - | 24.22 [32], 23.29 [39] |
Cu(DA)2+ | 16.53 ± 0.05 | 16.53 | 16.60 [32], 16.01 [39] | |
CuH2(DA)24+ | 45.37 ± 0.02 | - | 45.83 [32], 44.26 [39] | |
CuH(DA)23+ | 34.89 ± 0.05 | - | 35.66 [32] | |
Cu(DA)22+ | 24.00 ± 0.04 | 7.47 | 24.78 [32], 23.47 [39] |
Species | pH | λmax [nm] | g|| | g⊥ | A|| [10−4 cm−1] | A⊥ [10−4 cm−1] | Type of Chromophore |
---|---|---|---|---|---|---|---|
CuH(DA)3+ | 6.0 | 740 | 2.318 | 2.060 | 171 | <5 | {1N,1O} |
CuH2(DA)24+ | 8.0 | 658 | 2.292 2.250 | 2.048 2.051 | 156 203 | 18.44 31.90 | {2N} |
Interaction Scheme of Dopamine–Cu Complex | Energy [Hartree] | The Sum of Monomers [Hartree] | Interaction Energy [kcal/mol] |
---|---|---|---|
Cu_H_DA1 | −712.867571 | −712.596618 | −170.0 |
Cu_H_DA2 | −712.882092 | −712.550343 | −208.2 |
Cu_DA1 | −712.457026 | −712.057465 | −250.7 |
Cu_DA2 | −712.453956 | −712.091191 | −227.6 |
Cu_DA3 | −712.349837 | −711.909721 | −276.2 |
Interaction Scheme of Two Molecules of Protonated Dopamine–Cu Complex | Energy [Hartree] | The Sum of Monomers [Hartree] | Interaction Energy [kcal/mol] |
---|---|---|---|
Cu_H_DA2_1_A | −1228.788705 | −1228.383236 | −254.4 |
Cu_H_DA2_1_B | −1228.788130 | −1228.394962 | −246.7 |
Cu_H_DA2_2_A1 | −1228.807307 | −1228.239747 | −356.1 |
Cu_H_DA2_2_A2 | −1228.787186 | −1228.380653 | −255.1 |
Cu_H_DA2_2_B | −1228.760212 | −1228.372483 | −243.3 |
Cu_H_DA2_3_A | −1228.771797 | −1228.367769 | −253.5 |
Cu_H_DA2_3_B | −1228.772301 | −1228.368866 | −253.2 |
Cu_H_DA2_3_C | −1228.772810 | −1228.369879 | −252.8 |
Cu_H_DA2_4_A | −1228.769173 | −1228.375143 | −247.3 |
Cu_H_DA2_4_B | −1228.771144 | −1228.374988 | −248.6 |
Cu_H_DA2_4_C | −1228.776615 | −1228.397126 | −238.1 |
Cu_H_DA2_4_D | −1228.774482 | −1228.386332 | −243.6 |
Interaction Scheme of Two Molecules of Dopamine–Cu Complex | Energy [Hartree] | The Sum of Monomers [Hartree] | Interaction Energy [kcal/mol] |
---|---|---|---|
Cu_DA2_1_A | −1227.826653 | −1227.351948 | −297.9 |
Cu_DA2_1_B | −1227.813830 | −1227.355787 | −287.4 |
Cu_DA2_2_A | −1227.826654 | −1227.351935 | −297.9 |
Cu_DA2_2_B | −1227.797549 | −1227.350360 | −280.6 |
Cu_DA2_3 | −1227.865274 | −1227.356821 | −319.1 |
Cu_DA2_4 | −1227.836650 | −1227.364976 | −296.0 |
Systems | Species | Reaction | logβ | logKe |
---|---|---|---|---|
Cu(II)/DA/Ado | Cu(Ado)H3(DA)5+ | Cu(Ado)2+ + H3(DA)3+ ⇌ Cu(Ado)H3(DA)5+ | 38.86 ± 0.06 | 3.78 |
Cu(Ado)H2(DA)4+ | Cu(Ado)2+ + H2(DA)2+ ⇌ Cu(Ado)H2(DA)4+ | 35.83 ± 0.03 | 9.57 | |
Cu(Ado)H(DA)3+ | Cu(Ado)2+ + H(DA)+ ⇌ Cu(Ado)H(DA)3+ | 31.19 ± 0.03 | - | |
Cu(Ado)(DA)2+ | Cu(Ado)2+ + DA ⇌ Cu(Ado)(DA)2+ | 25.51 ± 0.03 | 22.63 | |
Cu(Ado)(DA)(OH)2 | Cu(Ado)(DA)2+ + 2H2O ⇌ Cu(Ado)(DA)(OH)2 + 2H+ | 12.09 ± 0.03 | 14.58 | |
Cu(Ado)(DA)(OH)42− | Cu(Ado)(DA)(OH)2 + 2H2O ⇌ Cu(Ado)(DA)(OH)42−+ 2H+ | −2.77 ± 0.04 | 13.14 | |
Cu(II)/DA/AMP | Cu(AMP)H4(DA)6+ | Cu2+ + H(AMP)+ + H3(DA)3+ ⇌ Cu(AMP)H4(DA)6+ | 44.29 ± 0.04 | - |
Cu(AMP)H3(DA)5+ | Cu(AMP)2+ + H3(DA)3+ ⇌ Cu(AMP)H3(DA)5+ | 39.09 ± 0.04 | 3.87 | |
Cu(AMP)H2(DA)4+ | Cu(AMP)2+ + H2(DA)2+ ⇌ Cu(AMP)H2(DA)4+ | 33.20 ± 0.06 | 6.80 | |
Cu(AMP)H(DA)3+ | Cu(AMP)2+ + H(DA)+ ⇌ Cu(AMP)H(DA)3+ | 26.97 ± 0.04 | - | |
Cu(II)/DA/ADP | Cu(ADP)H3(DA)5+ | Cu(ADP)2+ + H3(DA)3+ ⇌ Cu(ADP)H3(DA)5+ | 42.62 ± 0.04 | 3.43 |
Cu(ADP)H2(DA)4+ | Cu(ADP)2+ + H2(DA)2+ ⇌ Cu(ADP)H2(DA)4+ | 38.32 ± 0.03 | 7.95 | |
Cu(ADP)H(DA)3+ | Cu(ADP)2+ + H(DA)+ ⇌ Cu(ADP)H(DA)3+ | 32.39 ± 0.04 | - | |
Cu(ADP)(DA)2+ | Cu(ADP)2+ + DA ⇌ Cu(ADP)(DA)2+ | 25.05 ± 0.04 | 18.06 | |
Cu(Ado)(DA)(OH)+ | Cu(ADP)(DA)2+ + H2O ⇌ Cu(ADP)(DA)(OH)+ + H+ | 18.07 ± 0.04 | 7.02 | |
Cu(Ado)(DA)(OH)2 | Cu(ADP)(DA)(OH)+ + H2O ⇌ Cu(ADP)(DA)(OH)2 + H+ | 10.77 ± 0.04 | 6.70 | |
Cu(II)/DA/ATP | Cu(ATP)H3(DA)5+ | Cu(ATP)2+ + H3(DA)3+ ⇌ Cu(ATP)H3(DA)5+ | 41.73 ± 0.03 | 2.90 |
Cu(ATP)H2(DA)4+ | Cu(ATP)2+ + H2(DA)2+ ⇌ Cu(AMP)H2(DA)4+ | 35.23 ± 0.03 | 5.22 | |
Cu(ATP)H(DA)3+ | Cu(ATP)2+ + H(DA)+ ⇌ Cu(AMP)H(DA)3+ | 27.56 ± 0.07 | - |
Systems | Species | pH | λmax [nm] | g|| | g⊥ | A|| [10−4 cm−1] | A⊥ [10−4 cm−1] |
---|---|---|---|---|---|---|---|
Cu(II)/DA/Ado | Cu(Ado)H2(DA)4+ | 4.0 | 770 | 2.394 | 2.080 | 141 | 5.98 |
Cu(Ado)H(DA)3+ | 5.1 | 770 | 2.345 | 2.075 | 155 | <5 | |
Cu(Ado)(DA)2+ | 6.3 | 740 | 2.329 | 2.071 | 158 | <5 | |
Cu(Ado)(DA)(OH)2 | 7.0 | 725 | - | - | - | - | |
Cu(Ado)(DA)(OH)42− | 8.5 | 650 | - | - | - | - | |
Cu(II)/DA/AMP | Cu(AMP)H4(DA)6+ | 4.3 | 795 | - | - | - | - |
Cu(AMP)H3(DA)5+ | 5.5 | 745 | 2.345 | 2.072 | 156 | <5 | |
Cu(AMP)H2(DA)4+ | 6.3 | - | 2.316 | 2.069 | 173 | <5 | |
Cu(AMP)H(DA)3+ | 6.8 | - | 2.347 | 2.070 | 154 | <5 | |
Cu(II)/DA/ADP | Cu(ADP)H3(DA)5+ | 3.8 | 770 | 2.392 | 2.072 | 130 | 6.06 |
Cu(ADP)H2(DA)4+ | 5.1 | 754 | 2.342 | 2.071 | 168 | 5.41 | |
Cu(ADP)H(DA)3+ | 6.5 | 740 | 2.382 | 2.053 | 121 | <5 | |
Cu(ADP)(DA)(OH)2 | 8.0 | 657 | 2.292 | 2.048 | 162 | 17.69 | |
2.250 | 2.052 | 205 | 33.13 | ||||
Cu(II)/DA/ATP | Cu(ATP)H3(DA)5+ | 5.0 | 760 | 2.371 | 2.074 | 142 | <5 |
Cu(ATP)H2(DA)4+ | 7.0 | 748 | 2.362 | 2.076 | 149 | <5 | |
Cu(ATP)H(DA)3+ | 7.4 | - | 2.319 | 2.047 | 177 | 15.59 | |
2.250 | 2.052 | 203 | 30.30 |
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Sadowska, P.; Jankowski, W.; Bregier-Jarzębowska, R.; Pietrzyk, P.; Jastrząb, R. Deciphering the Impact of Nucleosides and Nucleotides on Copper Ion and Dopamine Coordination Dynamics. Int. J. Mol. Sci. 2024, 25, 9137. https://doi.org/10.3390/ijms25179137
Sadowska P, Jankowski W, Bregier-Jarzębowska R, Pietrzyk P, Jastrząb R. Deciphering the Impact of Nucleosides and Nucleotides on Copper Ion and Dopamine Coordination Dynamics. International Journal of Molecular Sciences. 2024; 25(17):9137. https://doi.org/10.3390/ijms25179137
Chicago/Turabian StyleSadowska, Patrycja, Wojciech Jankowski, Romualda Bregier-Jarzębowska, Piotr Pietrzyk, and Renata Jastrząb. 2024. "Deciphering the Impact of Nucleosides and Nucleotides on Copper Ion and Dopamine Coordination Dynamics" International Journal of Molecular Sciences 25, no. 17: 9137. https://doi.org/10.3390/ijms25179137