Abstract
Different synthetic strategies have been attempted for the synthesis of a glycosylpeptide resulting from the covalent bonding of a sugar residue to the C-terminal carboxyl group of an enkephalin related pentapeptide. The final structure is: Tyr-D-Met-Gly-Phe-Pro [N1.5-beta-D-glucopyranosyl] amide. The in vitro potency on the GPI test of this analogue was IC50 = 64.0 nM. However, its antinociceptive activity by tail immersion tests, after intraperitoneal administration, was 2000 and 200 times higher than morphine in rats and mice, respectively.
MeSH terms
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Analgesics / chemical synthesis*
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Animals
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Enkephalin, Methionine / analogs & derivatives*
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Enkephalin, Methionine / chemical synthesis
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Enkephalin, Methionine / pharmacology
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Enkephalins*
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Guinea Pigs
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In Vitro Techniques
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Indicators and Reagents
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Male
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Mice
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Mice, Inbred ICR
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Morphine / pharmacology
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Muscle Contraction / drug effects
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Muscle, Smooth / drug effects
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Muscle, Smooth / physiology
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Pain / physiopathology
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Rats
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Rats, Inbred Strains
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Structure-Activity Relationship
Substances
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Analgesics
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Enkephalins
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Indicators and Reagents
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enkephalin, Met(2)-ProNH2(5)(N(1.5)-glucopyranosyl)
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Enkephalin, Methionine
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Morphine