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Dopamine Autoxidation Is Controlled by Acidic pH.
Nejc Umek1,2, Blaž Geršak1, Neli Vintar1,3
1Department of Anesthesiology and Surgical Intensive Therapy, University Medical Centre Ljubljana, Ljubljana, Slovenia.
Frontiers in Molecular Neuroscience
|January 9, 2019
Summary
Dopamine can spontaneously oxidize, producing harmful reactive oxygen species. Quantum chemical methods reveal that acidic conditions in synaptic vesicles are crucial for dopamine stability, impacting Parkinson's disease.
Area of Science:
- Biochemistry
- Neuroscience
- Quantum Chemistry
Background:
- Dopamine and noradrenaline, unlike other biogenic amines, undergo non-enzymatic autoxidation.
- This reaction generates superoxide anions and reactive oxygen species (ROS).
- The autoxidation occurs in aqueous solutions, not solely at mitochondrial membranes.
Purpose of the Study:
- To elucidate the reaction mechanism of dopamine autoxidation using quantum chemical methods.
- To investigate the factors influencing dopamine stability.
- To discuss the pathophysiological implications in Parkinson's disease and drug abuse.
Main Methods:
- Quantum chemical calculations were employed to study the reaction mechanism.
- Experimental rate constants were considered for comparison.
- The role of pH in dopamine stability was assessed.
Main Results:
- The rate-limiting step involves hydroxide ion formation attacking the amino group, leading to aminochrome.
- Dopamine autoxidation rate is comparable to monoamine oxidase B catalyzed decomposition.
- Acidic pH within synaptic vesicles is essential for dopamine stability over days.
Conclusions:
- Dopamine's autoxidation mechanism is elucidated, highlighting the role of quantum chemistry.
- Synaptic vesicle acidity is critical for maintaining dopamine stability.
- Findings offer insights into Parkinson's disease and pathologies linked to amphetamine and cocaine.
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