Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Activity Profiles of Linear, Cyclic Monomer and Cyclic Dimer of Enkephalin

  • Received : 2011.09.15
  • Accepted : 2011.11.21
  • Published : 2012.01.20
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Abstract

The cyclic dimers of enkephalin were isolated as minor components during the solution synthesis of the corresponding cyclic monomers. The ratio of cyclic dimer to monomer was approximately 1:4 from the percent of yields. In the receptor binding assay of two cyclic dimmers, ($Tyr_2-C[D-Glu-Phe-gPhe]_2$ 6, $Tyr_2-C[D-Asp-Phe-gPhe-rLeu]_2$ 8), both analogs exhibited the high preference for ${\delta}$ receptor compared to monocyclic counterparts. In the nociceptive activity, both showed about 5 times less potent than the cyclic monomers. The repeated synthesis of 14-membered cyclic analog, Tyr-C[D-Glu-Phe-gPhe-D-rLeu] 14, which was known as having three distinct cis-trans isomers, gave rise to apparently different conformational analog arousing only trans isomer. In the receptor binding assay, it showed tremendously high selectivity toward ${\mu}$ receptor $({\delta}/{\mu}=160)$.

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