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Partially Modified Retro-Inverso-Enkephalinamides: Topochemical Long-Acting Analogs in Vitro and in Vivo
Abstract
The synthesis of four enkephalinamide analogs is described in which the peptide bond between residues 4 and 5 is reversed with or without simultaneous reversal of the carboxyl-terminal amide bond. These so-called partially modified retro-inverso-isomers are new, potent, topochemical analogs of the enkephalins. Tests, both in vitro and in vivo, have shown that these analogs are considerably longer acting than any previously studied enkephalins. Thus, partial reversal of the peptide bonds of the backbone can result in peptides with enhanced activity compared to a parent compound, provided that the structural complementarity of both the side chains and end groups are conserved.
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References 25 · Cited by 100
Research works printed but not linked: 32
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Metadata
- Authors
- Chorev, M., Shavitz, R., Goodman, M., Minick, S., & Guillemin, R.
- Affiliations
- University of California San Diego (US)
- Salk Institute for Biological Studies (US)
- ORCID
- Chorev, Michael
- Venue
- Science
- Published
- 1979-06-15
- Volume
- 204
- Issue
- 4398
- Pages
- 1210-1212
- ISSN
- 0036-8075 (ISSN-L)
- 1095-9203
- OpenAlex
- W2062551480
- Cited by
- 100
- References
- 25
- Citations by year
- 2026: 2 · 2025: 4 · 2024: 4 · 2022: 2 · 2021: 3 · 2019: 1 · 2018: 1 · 2017: 1 · 2016: 2 · 2015: 1 · 2014: 1 · 2012: 3
- FWCI
- 1.54
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Science (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Analysis
- Life Sciences › Neuroscience › Cellular and Molecular Neuroscience › Neuropeptides and Animal Physiology
- Physical Sciences › Materials Science › Biomaterials › Supramolecular Self-Assembly in Materials
- Keywords
- enkephalin, opioid agonists, peptide synthesis
- MeSH terms
- Animals, Behavior, Animal, Brain, Endorphins, Enkephalins, Structure-Activity Relationship, Rats
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