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Scientific article
English

Electronic and Conformational Effects on the Lipophilicity of Isomers and Analogs of the Neurotoxin 1-Methyl-4-Phenylpyridinium (Mpp+)

Contributors

Altomare, Cosimo; Carrupt, Pierre-Alain; el Tayar, Nabil; Testa, Bernard; Nagatsu, T.

Published in

Helvetica chimica acta, vol. 74, no. 2, p. 290-296

Publication date

1991

Abstract

A number of isomers and analogs of the neurotoxin 1-methyl-4-phenylpyridinium (MPP+) were examined for their lipophilic behavior. Their partition coefficients in the 1-octanol/H-2O system were measured by centrifugal partition chromatography (CPC), which, being much faster and markedly more precise than the classical shakeflask method, proved a very promising alternative for assessing lipophilicity. A smaller-than-expected lipophilicity was shown by the ortho-isomer of MPP+ (M2PP+) and is explained in terms of electronic effects and rigidity, as revealed by UV and NMR spectroscopy, and conformational analysis. Implications of lipophilicity in modulating the in vivo dopaminergic neurotoxicity of the examined compounds are also discussed

UNIGE affiliation entities

Not a UNIGE publication

Citation (ISO format)

ALTOMARE, Cosimo et al. Electronic and Conformational Effects on the Lipophilicity of Isomers and Analogs of the Neurotoxin 1-Methyl-4-Phenylpyridinium (Mpp+). In: Helvetica chimica acta, 1991, vol. 74, n° 2, p. 290–296. doi: 10.1002/hlca.19910740205

Identifiers

Journal ISSN

0018-019X
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Technical informations

Creation

06/08/2010 10:46:37

First validation

06/08/2010 10:46:37

Update

14/03/2023 15:56:14

Status update

14/03/2023 15:56:14

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