Document Detail

3,4-Dihydroxyphenylethylamine, L-3,4-dihydroxyphenylalanine and 3,4,5-trihydroxyphenylalanine: oxidation and binding to membranes. A comparative study of a neurotransmitter, a precursor and a neurotransmitter candidate in primitive nervous systems.
MedLine Citation:
PMID:  1973046     Owner:  NLM     Status:  MEDLINE    
At neutral (7.0) and slightly basic (8.2) pH, L-3,4-dihydroxyphenylalanine (L-DOPA), 3,4,5-trihydroxyphenylalanine (5-OH-DOPA) and 3,4-dihydroxyphenylethylamine (dopamine) undergo autoxidation. The binding of radiolabeled oxidation products of L-DOPA, 5-OH-DOPA and dopamine to membrane proteins was compared by a filtration procedure. Membranes from tentacles of the sea anemone Metridium senile bind significantly more 5-OH-DOPA than L-DOPA and dopamine. Membranes from rat brain and brains from the three-spined stickleback Gasterosteus aculeatus, bind significantly more dopamine than L-DOPA and 5-OH-DOPA. Membranes from Metridium contain an o-diphenol O2: oxidoreductase (tyrosinase). In the absence of inhibitors, enzymatic oxidation causes a fiftyfold increase in binding of L-DOPA and a more than tenfold increase in binding of dopamine, whereas the binding of 5-OH-DOPA only is increased by 10%. It is concluded than 5-OH-DOPA more easily undergo autoxidation than L-DOPA and dopamine, but its quinone form is probably less reactive with membrane proteins. The suitability of tyrosinase-mediated biosynthesis of L-DOPA and 5-OH-DOPA versus tyrosine hydroxylase-mediated biosynthesis of L-DOPA and dopamine in primitive nervous systems and in the vertebrate CNS is discussed on the basis of the cytotoxic potential through irreversible binding to membrane proteins of oxidation products of the catechol compounds formed.
M Carlberg
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of neural transmission. General section     Volume:  81     ISSN:  -     ISO Abbreviation:  J. Neural Transm. Gen. Sect.     Publication Date:  1990  
Date Detail:
Created Date:  1990-08-13     Completed Date:  1990-08-13     Revised Date:  2014-06-03    
Medline Journal Info:
Nlm Unique ID:  9002201     Medline TA:  J Neural Transm Gen Sect     Country:  AUSTRIA    
Other Details:
Languages:  eng     Pagination:  111-9     Citation Subset:  IM    
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MeSH Terms
Brain / metabolism*
Cnidaria / metabolism*
Dihydroxyphenylalanine / analogs & derivatives*,  metabolism*
Dopamine / metabolism*
Fishes / metabolism*
Rats, Inbred Strains
Sea Anemones / metabolism*
Reg. No./Substance:
16032-83-0/5-hydroxydopa; 63-84-3/Dihydroxyphenylalanine; VTD58H1Z2X/Dopamine

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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