MPP+
 | |
| Names | |
|---|---|
| IUPAC name
1-Methyl-4-phenylpyridin-1-ium | |
| Other names
Cyperquat; 1-Methyl-4-phenylpyridinium; N-Methyl-4-phenylpyridine | |
| Identifiers | |
39794-99-5  | |
| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:641  |
| ChEMBL | ChEMBL311617 |
| ChemSpider | 36101 |
| EC Number | 248-939-7 |
| 4568 | |
| MeSH | 1-Methyl-4-phenylpyridinium |
| PubChem | 39484 |
| |
| |
| Properties | |
| C12H12N+ | |
| Molar mass | 170.25 g/mol |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
MPP+ (1-methyl-4-phenylpyridinium) is a positively charged molecule with chemical formula C12H12N+. It is toxic and acts by interfering with oxidative phosphorylation in mitochondria by inhibiting complex I, leading to the depletion of ATP and cell death.[1] Mitochondria in cells treated with MPP+ also display a phenotype indicative of apoptosis: small, round, and fewer in number.[2] It also inhibits the synthesis of catecholamines, reduces levels of dopamine and cardiac norepinephrine, and inactivates tyrosine hydroxylase.[1]
The neurotoxin MPTP is converted in the brain into MPP+ by the enzyme MAO-B, causing parkinsonism in primates by killing certain dopamine-producing neurons in the substantia nigra. MPP+-induced neurodegeneration is specific to dopamine neurons and can be prevented by drug treatment or by limiting the function of the dopamine transporter.[3]
The chloride salt of MPP+ has been used as a herbicide under the trade name cyperquat and is structurally similar to the herbicide paraquat.
In a rat model of Parkinson's disease, nobiletin, a flavonoid found in citrus, can rescue dopaminergic neurons from degeneration caused by treatment with MPP+.[4]
References
- 1 2 PubChem Compound entry on MPP+
- ↑ Wiemerslage L, Lee D (2016). "Quantification of mitochondrial morphology in neurites of dopaminergic neurons using multiple parameters.". J Neurosci Methods. doi:10.1016/j.jneumeth.2016.01.008. PMID 26777473.
- ↑ Wiemerslage L, Schultz BJ, Ganguly A, Lee D (2013). "Selective degeneration of dopaminergic neurons by MPP(+) and its rescue by D2 autoreceptors in Drosophila primary culture.". J Neurochem. 126 (4): 529–40. doi:10.1111/jnc.12228. PMID 23452092.
- ↑ Jeong, Kyoung Hoon; Jeon, Min-Tae; Kim, Heung Deok; Jung, Un Ju; Jang, Min Cheol; Chu, Jin Woo; Yang, Seung Jun; Choi, Il Yoon; Choi, Myung-Sook (2014-10-17). "Nobiletin Protects Dopaminergic Neurons in the 1-Methyl-4-Phenylpyridinium-Treated Rat Model of Parkinson's Disease". Journal of Medicinal Food. 18 (4): 409–414. doi:10.1089/jmf.2014.3241. ISSN 1096-620X.