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Chemical Compound Review:

CHEMBL6224 4-phenyl-1,2,3,6- tetrahydropyridine

Synonyms: SureCN415545, AG-D-14107, NSC-54451, CHEBI:100242, Oprea1_874761, ...

Chiba, K. et al., Chen, Q. et al., Modi, S. et al., Naritomi, Y. et al., Goulet, M. et al., et al.

Ishida, Hattori, Yamamoto, Iwashita, Mihara, Matsuoka,

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Disease relevance of NSC 54451

Of the analogues tested, 4-phenylpyridine (PPY) and 4-phenyl-1,2,3,6-tetrahydropyridine (PTP) given in single i.p. doses to mice caused marked hypothermia [1].

High impact information on NSC 54451

When the reaction is carried out with nicotinamide adenine dinucleotide phosphate (reduced) (NADPH) and recombinant human NADPH-cytochrome P450 reductase, a second product, identified as 1-methyl-4-(4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine, is formed in addition to 4-phenyl-1,2,3,6-tetrahydropyridine [2].
Continuous or pulsatile chronic D2 dopamine receptor agonist (U91356A) treatment of drug-naive 4-phenyl-1,2,3,6-tetrahydropyridine monkeys differentially regulates brain D1 and D2 receptor expression: in situ hybridization histochemical analysis [3].
1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), a selective neurotoxin to the nigrostriatal dopaminergic neurons, has been shown to be metabolized by microsomal flavin-containing monooxygenase (FMO) to 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine N-oxide and by cytochrome (cyt.) P-450 to 4-phenyl-1,2,3,6-tetrahydropyridine in the liver [4].
A multiple Gradient Recalled Echo MRI sequence was used to map spatial and temporal changes in the rate of MR signal decay (R2*) in response to L-3,4-dihydroxyphenylalanine (levodopa) in the striatal dopaminergic system of a rhesus monkey unilaterally lesioned with 4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride (MPTP) [5].
The desmethyl derivative, 4-phenyl-1,2,3,6-tetrahydropyridine (PTP), was oxidised by MAO-B to form the corresponding dihydropyridine [6].

Biological context of NSC 54451

A cDNA of amine sulfotransferase-RB1 (AST-RB1), which efficiently catalyzes 4-phenyl-1,2,3,6-tetrahydropyridine (PTHP) sulfation, has been isolated by immunoscreening of a rabbit liver cDNA library [7].

Anatomical context of NSC 54451

An alicyclic amine N-sulfotransferase sulfonating 4-phenyl-1,2,3,6-tetrahydropyridine (PTHP) was purified from female rat liver cytosol and showed a homogenous band with a molecular weight of 30500 on sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) [8].

Gene context of NSC 54451

4-Phenyl-1,2,3,6-tetrahydropyridine, an excellent fragment to improve the potency of PARP-1 inhibitors [9].

References

Central hypothermic effects of some analogues of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) and 1-methyl-4-phenylpyridinium ion (MPP+). Satoh, N., Yonezawa, A., Tadano, T., Kisara, K., Arai, Y., Kinemuchi, H. Neurosci. Lett. (1987) [Pubmed]
1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine as a substrate of cytochrome P450 2D6: allosteric effects of NADPH-cytochrome P450 reductase. Modi, S., Gilham, D.E., Sutcliffe, M.J., Lian, L.Y., Primrose, W.U., Wolf, C.R., Roberts, G.C. Biochemistry (1997) [Pubmed]
Continuous or pulsatile chronic D2 dopamine receptor agonist (U91356A) treatment of drug-naive 4-phenyl-1,2,3,6-tetrahydropyridine monkeys differentially regulates brain D1 and D2 receptor expression: in situ hybridization histochemical analysis. Goulet, M., Morissette, M., Calon, F., Blanchet, P.J., Falardeau, P., Bédard, P.J., Di Paolo, T. Neuroscience (1997) [Pubmed]
Characterization of hepatic microsomal metabolism as an in vivo detoxication pathway of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in mice. Chiba, K., Kubota, E., Miyakawa, T., Kato, Y., Ishizaki, T. J. Pharmacol. Exp. Ther. (1988) [Pubmed]
Mapping drug-induced changes in cerebral R2* by Multiple Gradient Recalled Echo functional MRI. Chen, Q., Andersen, A.H., Zhang, Z., Ovadia, A., Gash, D.M., Avison, M.J. Magnetic resonance imaging. (1996) [Pubmed]
The interactions of monoamine oxidase with some derivatives of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP). Sullivan, J.P., Tipton, K.F. J. Neural Transm. Suppl. (1990) [Pubmed]
Molecular cloning and expression of an amine sulfotransferase cDNA: a new gene family of cytosolic sulfotransferases in mammals. Yoshinari, K., Nagata, K., Ogino, M., Fujita, K., Shiraga, T., Iwasaki, K., Hata, T., Yamazoe, Y. J. Biochem. (1998) [Pubmed]
Isolation and characterization of an alicyclic amine N-sulfotransferase from female rat liver. Naritomi, Y., Niwa, T., Shiraga, T., Iwasaki, K., Noda, K. Biol. Pharm. Bull. (1994) [Pubmed]
4-Phenyl-1,2,3,6-tetrahydropyridine, an excellent fragment to improve the potency of PARP-1 inhibitors. Ishida, J., Hattori, K., Yamamoto, H., Iwashita, A., Mihara, K., Matsuoka, N. Bioorg. Med. Chem. Lett. (2005) [Pubmed]

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