259151-53-6

Basic information

• Product Name: L-Tyrosyl-D-penicillaminyl-glycyl-L-phenylalanyl-D-cysteine cyclic (2-5)-thioether
• Synonyms: (3S,6S,12S)-6-Benzyl-13,13-dimethyl-5,8,11-trioxo-12-(L-tyrosylamino)-1-thia-4,7,10-triazacyclotridecane-3-carboxylic acid
• CAS NO: 259151-53-6
• Molecular Formula: C₂₈H₃₅N₅O₇S
• Molecular Weight: 585.68445
• Mol File: 259151-53-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: L-Tyrosyl-D-penicillaminyl-glycyl-L-phenylalanyl-D-cysteine cyclic (2-5)-thioether(CAS DataBase Reference)
• NIST Chemistry Reference: L-Tyrosyl-D-penicillaminyl-glycyl-L-phenylalanyl-D-cysteine cyclic (2-5)-thioether(259151-53-6)
• EPA Substance Registry System: L-Tyrosyl-D-penicillaminyl-glycyl-L-phenylalanyl-D-cysteine cyclic (2-5)-thioether(259151-53-6)

Safety Data

• Hazardous Substances Data: 259151-53-6(Hazardous Substances Data)

Relevant articles and documents

Synthesis and biological activities of cyclic lanthionine enkephalin analogues: δ-opioid receptor selective ligands

The synthesis and biological test results of a series of enkephalin analogues incorporating the lanthionine modification are presented. The syntheses of four monosulfide-bridged analogues of enkephalins, Tyr-c[D-AlaL-Gly-Phe-D-AlaL]-OH (1a), Tyr-c[D-ValL-Gly-Phe-D-AlaL]-OH (1b), Tyr-c[D-AlaL-Gly-Phe-AlaL]-OH (1c), and Tyr-c[D-ValL-Gly-Phe-AlaL]-OH (1d), where AlaL and ValL denote the lanthionine amino acid ends linked by a monosulfide bridge to form the lanthionine structure, were successfully carried out via preparation of the linear peptide on solid support and cyclization in solution. In vitro binding assays against μ, δ-, and κ-opioid receptors and in vitro tests using GPI and MVD assays revealed that the dimethyl lanthionine analogues 1b and 1d, denoted as D-ValL in position 2, show substantial selectivity toward the δ-opioid receptor, while the unsubstituted analogues 1a and 1c, denoted as D-AlaL in position 2, bind to both μ- and δ-opioid receptors. The in vivo thermal escape assay by intrathecal administration showed that the analogues 1b and 1d are among the most potent ligands at producing antinociception through the δ-opioid receptor. The picomolar potencies of analogues 1a and 1c in the intrathecal (it.) assay strongly indicate that μ- and δ-opioid receptors interact synergistically to modulate the antinociceptive responses.