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J Med Chem. 2008 Apr 24;51(8):2571-4. doi: 10.1021/jm701404s. Epub 2008 Mar 28.

Blood-brain barrier penetration by two dermorphin tetrapeptide analogues: role of lipophilicity vs structural flexibility.

Author information

1
Organic Chemistry Department, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium.

Abstract

Two dermorphin analogues having an almost identical structure but different structural flexibility were compared for opioid activity. In 1 the aromatic side chains were incorporated into a lactam structure, while in 2 N-amide alkylation was retained but the side chains were flexible. Both compounds produced comparable antinociceptive effects in the mouse tail flick test after peripheral administration. This indicates that lipophilicity, rather than side chain flexibility, is the key determinant for blood-CNS barrier penetration.

PMID:
18370374
DOI:
10.1021/jm701404s
[Indexed for MEDLINE]

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