OPIATE-LIKE PEPTIDES .4. KYOTORPHIN AND ITS ANALOGS - SYNTHESIS AND ANALGESIC ACTIVITY

  • 1 January 1983
    • journal article
    • research article
    • Vol. 35  (6) , 473-480
Abstract
L-Tyrosyl-L-arginine (kyotorphin) and its 8 analogs [the benzylesters of N-benzyloxycarbonyl-O-benzyl-D-tyrosyl-N-G-nitro-L-arginine, N-benzyloxycarbonyl-O-benzyl-L-tyrosyl-N->-benzyloxycarbonyl-L-lysine, N-benzyloxycarbonyl-O-benzyl-D-tyrosyl-N-.epsilon.-benzyloxycarbonyl-L-lysine, N-benzyloxycarbonyl-O-benzyl-L-tyrosyl-N-.delta.-benzyloxycarbonyl-L-ornithine, N-benzyloxycarbonyl-O-benzyl-L-tyrosyl-N-.delta.-benzyloxycarbonyl-D-ornithine and N-benzyloxycarbonyl-O-benzyl-D-tyrosyl-N-.delta.-benzyloxycarbonyl-L-ornithine and the methyl esters of N-benzyloxycarbonyl-O-benzyl-L-tyrosyl-L-citrulline and N-benzyloxycarbonyl-O-benzyl-D-tyrosyl-L-citrulline] were synthesized using the EEDQ [N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline] method. The analgesic activity and neurotoxic effect of all dipeptides were examined in rats. Three of the analogs investigated displayed weak analgesic activity occurring on the administration of doses which exert the neurotoxic effect. For 3 other analogs the neurotoxic effect precedes the possible analgesic effect. The remaining 2 analogs were biologically inactive.

This publication has 1 reference indexed in Scilit: