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The effects of biologically important divalent and trivalent metal cations on the cyclization step of dopamine autooxidation reaction [Elektronski vir] : a quantum chemical studyUmek, NejcDopamine is the most essential monoaminergic neurotransmitter involved in the pathophysiology of neurodegenerative disorders, and its autooxidation has been recognized as one of the potential trigger ... factors for dopaminergic neuron loss. The cyclization of dopamine o-quinone was shown to be the irreversible and rate-limiting step of the autooxidation reaction at physiologic pH values. Furthermore, various metal ions such as Al3+, Fe3+, Fe2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Pb2+, and Mn2+ have been clinically associated with neurodegeneration, especially Parkinsonism and dementia. It has been proposed that these metal ions could increase the rate of the dopamine autooxidation reaction; however, the exact mechanism has not yet been fully understood. Using advanced quantum chemical calculations with the inclusion of solvent effects we showed that except for Mn2+, the studied metal cations could form complexes with dopamine o–quinone and significantly increase the dopamine o-quinone cyclization rate in aqueous solution; first, by enabling the cyclization to proceed spontaneously without the attack of the unprotonated amino group by hydroxide ion; second, by decreasing the intrinsic activation energy; and third, by decreasing the free energy of protonated amino group deprotonation. The latter also decreases the protective effect of acidic pH on dopamine autooxidation found in synaptic vesicles. The results are fully consistent with experimental data and provide deeper understanding of the effects of metal cations on the dopamine autooxidation reaction at physiologic pH values.Source: Arabian journal of chemistry. - ISSN 1878-5379 (Vol. 15, iss. 10, 2022, str. 1-10)Type of material - e-article ; adult, seriousPublish date - 2022Language - englishCOBISS.SI-ID - 117026819
Author
Umek, Nejc
Topics
dopamine |
autooxidation |
neurodegeneration |
dopamin |
avtooksidacija |
nevrodegeneracija
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Umek, Nejc | 51820 |
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