The DOI matches its Crossref record; 44 of the 44 references it cites were found in a registry or an index.
Cyclic parathyroid hormone-related protein antagonists: lysine 13 to aspartic acid 17 [i to (i + 4)] side chain to side chain lactamization
Abstract
Cyclization of parathyroid hormone related protein (7-34)amide [PTHrP(7-34)NH2] via covalent bond formation between the epsilon-amino of Lys13 and the beta-carboxyl of Asp17 yielded a 20-membered ring lactam. This analogue, [Lys13,Asp17]PTHrP(7-34)NH2, was 5-10-fold more potent than the linear parent peptide (Kb = 15 and 18 nM in PTH receptor binding assays, and Ki = 130 and 17 nM in PTH-stimulated adenylate cyclase assays in bovine renal cortical membrane and in human bone derived B10 cells, respectively). In contrast, a linear analogue in which charges in positions 13 and 17 were eliminated and other stereoisomers of the above-mentioned lactam in which either Lys13 and/or Asp17 were replaced by the corresponding D-amino acids were much less potent with regard to antagonist bioactivity than the parent peptide. The rationale for the design of the lactam as well as the conformational implications for the PTHrP sequence in light of reported models suggested for the 1-34 peptide are described. The potential use of conformationally constrained analogues for elucidating the "bioactive conformation" of antagonists and for the design of substantially simplified molecular structures for antagonists is discussed.
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A Parathyroid Hormone-Related Protein Implicated in Malignant Hypercalcemia: Cloning and Expression
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Conformation and Biological Activity of Cyclic Peptides
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Bis-penicillamine enkephalins possess highly improved specificity toward delta opioid receptors.
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Parathyroid hormone-related protein purified from a human lung cancer cell line.
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Self-citationSternbach, L. H. (1979) · Journal of Medicinal Chemistry · doi:10.1021/jm00187a001 · Cited by 447
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Conformational restrictions of biologically active peptides via amino acid side chain groups
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Parathyroid Hormone-Related Protein of Malignancy: Active Synthetic Fragments
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Metadata
- Authors
- Chorev, M., Roubini, E., McKee, R. L., Gibbons, S. W., Goldman, M. E., Caulfield, M. P., & Rosenblatt, M.
- Affiliations
- Hebrew University of Jerusalem (IL)
- ORCID
- Chorev, Michael
- Venue
- Biochemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1991-06-18
- Volume
- 30
- Issue
- 24
- Pages
- 5968-5974
- ISSN
- 0006-2960 (ISSN-L)
- 1520-4995
- OpenAlex
- W2075824919
- Cited by
- 107
- References
- 44
- Citations by year
- 2026: 1 · 2025: 1 · 2023: 1 · 2022: 3 · 2021: 3 · 2020: 7 · 2019: 3 · 2018: 5 · 2017: 4 · 2015: 6 · 2014: 8 · 2013: 3 · 2012: 2
- FWCI
- 0.93
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Biochemistry (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Analysis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Protein Structure and Dynamics
- Life Sciences › Neuroscience › Cellular and Molecular Neuroscience › Neuropeptides and Animal Physiology
- Keywords
- parathyroid hormone-related protein, cyclic peptide analogues, lactamization, peptide cyclization, conformationally constrained analogues, bioactive conformation, adenylate cyclase activation
- MeSH terms
- Adenylyl Cyclases, Amino Acid Sequence, Animals, Cattle, Cell Line, Cell Membrane, Humans, Indicators and Reagents, Kidney Cortex, Lactams, Molecular Sequence Data, Parathyroid Hormone, Peptides, Cyclic, Protein Conformation, Proteins, Receptors, Cell Surface, Osteosarcoma, Structure-Activity Relationship, Receptors, Parathyroid Hormone, Parathyroid Hormone-Related Protein
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