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Biological properties of transition-metal organometallic compounds. 3. beta-Ferrocenylalanine


Biological properties of transition-metal organometallic compounds. 3. beta-Ferrocenylalanine



Journal of Medicinal Chemistry 22(4): 424-428



ISSN/ISBN: 0022-2623

PMID: 430480

DOI: 10.1021/jm00190a013

The effects of DL-.beta.-ferrocenylalanine (1), five DL-halophenylalanines (p-F, 2; m-F, 3; o-F, 4; p-Cl, 5; p-Br, 6), L-.beta.-(2-pyridyl)alanine (7) and DL-.beta.-(6-methyl-2-pyridyl)alanine (8) on the growth of Leuconostoc mesenteroides and as inhibitors of phenylalanine decarboxylase from Streptococcus fecalis, hog kidney aromatic L-amino acid decarboxylase and rat liver phenylalanine hydroxylase were investigated. None of the compounds supported bacterial growth in the absence of L-Phe, but they inhibited growth in the presence of L-Phe in the order 2 .mchgt. 4 > 3 .simeq. 7 > 5 > 6; 8 and 1 were inactive. Both decarboxylases were inhibited by the analogs to a similar extent, the inhibition decreasing in the order 1 > 6 > 5 > 2 > 8 .apprx. 7. Compound 1 was a competitive inhibitor of the hog kidney enzyme with a Ki of 7.2 mM; L-Phe had a Km of 48.8 mM. Inhibition of the phenylalanine hydroxylase (DMPH4 cofactor) decreased in the order 2 > 1 > 3 > 4 > 5 > 6 7 > 8 over a range from 73-2% inhibition. Compound 1 gave noncompetitive inhibition with respect to L-Phe and mixed inhibition with respect to DMPH4 cofactor. This pattern of inhibition kinetics is apparently unique, as other known inhibitors either compete for substrate (e.g., 2 and 5) or with cofactor (e.g., norepinephrine or other catehcol catechol compounds). Perhaps 1 affects the enzyme through interaction at an allosteric or regulatory site previously proposed to account for the activation observed upon preincubation of the enzyme with its normal substrate L-Phe.

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