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Cyclic parathyroid hormone-related protein antagonists: lysine 13 to aspartic acid 17 [i to (i + 4)] side chain to side chain lactamization

Chorev, Michael, Roubini, Eliahu, McKee, Roberta L., Gibbons, Susan W., Goldman, Mark E., Caulfield, Michael P., Rosenblatt, Michael·1991·Biochemistry

DOI 10.1021/bi00238a022

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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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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
DOI: 10.1021/bi00238a022
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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Cyclic parathyroid hormone-related protein antagonists: lysine 13 to aspartic acid 17 [i to (i + 4)] side chain to side chain lactamization

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