Bioactive N‐terminal undecapeptides derived from parathyroid hormone: the role of α‐helicity*

Barazza, A.; Wittelsberger, A.; Fiori, N.; Schievano, E.; Mammi, S.; Toniolo, C.; Alexander, J.M.; Rosenblatt, M.; Peggion, E.; Chorev, M.

doi:10.1111/j.1399-3011.2005.00207.x

Cited by 25Chemical Synthesis and AnalysisNeuropeptides and Animal PhysiologyParathyroid Disorders and Treatments

Bioactive N‐terminal undecapeptides derived from parathyroid hormone: the role of α‐helicity*

Barazza, A., Wittelsberger, A., Fiori, N., Schievano, E., Mammi, S., Toniolo, C., Alexander, J.M., Rosenblatt, M. +2 more·2005·The Journal of Peptide Research

DOI 10.1111/j.1399-3011.2005.00207.x

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Abstract

Abstract: The N‐terminal 1–34 segment of parathyroid hormone (PTH) is fully active in vitro and in vivo and it can reproduce all biological responses in bone characteristic of the native intact PTH. Recent studies have demonstrated that N‐terminal fragments presenting the principal activating domain such as PTH(1–11) and PTH(1–14) with helicity‐enhancing substitutions yield potent analogues with PTH(1–34)‐like activity. To further investigate the role of α‐helicity on biological potency, we designed and synthesized by solid‐phase methodology the following hPTH(1–11) analogues substituted at positions 1 and/or 3 by the sterically hindered and helix‐promoting Cα‐tetrasubstituted α‐amino acids α‐amino isobutyric acid (Aib), 1‐aminocyclopentane‐1‐carboxylic acid (Ac 5 c) and 1‐aminocyclohexane‐1‐carboxylic acid (Ac 6 c): Ac 5 c‐V‐Aib‐E‐I‐Q‐L‐M‐H‐Q‐R‐NH 2 (I); Aib‐V‐Ac 5 c‐E‐I‐Q‐L‐M‐H‐Q‐R‐NH 2 (II); Ac 6 c‐V‐Aib‐E‐I‐Q‐L‐M‐H‐Q‐R‐NH 2 (III); Aib‐V‐Ac 6 c‐E‐I‐Q‐L‐M‐H‐Q‐R‐NH 2 (IV); Aib‐V‐Aib‐E‐I‐Q‐L‐M‐H‐Q‐R‐NH 2 (V); S‐V‐Aib‐E‐I‐Q‐L‐M‐H‐Q‐R‐NH 2 (VI), S‐V‐Ac 5 c‐E‐I‐Q‐L‐M‐H‐Q‐R‐NH 2 (VII); Ac 5 c‐V‐S‐E‐I‐Q‐L‐M‐H‐Q‐R‐NH 2 (VIII); Ac 6 c‐V‐S‐E‐I‐Q‐L‐M‐H‐Q‐R‐NH 2 (IX); Ac 5 c‐V‐Ac 5 c‐E‐I‐Q‐L‐M‐H‐Q‐R‐NH 2 (X); Ac 6 c‐V‐Ac 6 c‐E‐I‐Q‐L‐M‐H‐Q‐R‐NH 2 (XI). All analogues were biologically evaluated and conformationally characterized in 2,2,2‐trifluoroethanol (TFE) solution by circular dichroism (CD). Analogues I–V, which cover the full range of biological activity observed in the present study, were further conformationally characterized in detail by nuclear magnetic resonance (NMR) and computer simulations studies. The results of ligand‐stimulated cAMP accumulation experiments indicated that analogues I and II are active, analogues III, VI and VII are very weakly active and analogues IV, V, VIII–XI are inactive. The most potent analogue, I exhibits biological activity 3500‐fold higher than that of the native PTH(1–11) and only 15‐fold weaker than that of the native sequence hPTH(1–34). Remarkably, the two most potent analogues, I and II, and the very weakly active analogues, VI and VII, exhibit similar helix contents. These results indicate that the presence of a stable N‐terminal helical sequence is an important but not sufficient condition for biological activity.

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Parathyroid Hormone–Receptor Interactions
Wittelsberger, A., & Rosenblatt, M. (2008) · Elsevier eBooks · doi:10.1016/b978-0-12-373884-4.00048-3 · Cited by 4 · see citing works
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Endosomal PTH Receptor Signaling Through cAMP and Its Consequence for Human Medicine
Sutkevičiu̅tė, I., Jean‐Alphonse, F., & Vilardaga, J. (2017) · Topics in medicinal chemistry · doi:10.1007/7355_2017_1 · Cited by 3 · see citing works
Prediction of Parathyroid Hormone Signalling Potency Using SVMs
Yoo, A., Ko, S., Lim, S.-K., Lee, W., & Yang, D. R. (2009) · Molecules and Cells · doi:10.1007/s10059-009-0082-3 · Cited by 1 · see citing works
BindingDB Entry 50032559: Side chain cyclization based on serine residues: synthesis, structure, and activity of a novel cyclic analogue of the parathyroid hormone fragment 1-11.
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BindingDB Entry 50041505: Synthesis and biological activity of nociceptin/orphanin FQ analogues substituted in position 7 or 11 with Calpha,alpha-dialkylated amino acids.
BindingDB (2013) · UC San Diego · doi:10.7270/q22r3svp

Bioactive N-terminal Undecapeptides Derived from Parathyroid Hormone. The Role of alpha-Helicity
A., B., Fiori, N., Alexander, J. M., M., R., M., C., Schievano, E., MAMMI, S., & Peggion, E. (2004) · Padua Research Archive (University of Padova)
Self-citation
Structure-Function Relationship of Analogues of PTH(1-11) Containing a Combination of Aib and (αMe)Val.
CAPORALE, A., Schievano, E., Mammi, S., Peggion, E., Fiori, N., WITTELSBERGER, A., & CHOREV, M. (2007) · Padua Research Archive (University of Padova)
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Structure-function relationship of analogues of PTH (1-11) containing a combination of C-alpha-tetrasubstituited amino acids
Caporale, A., Fiori, N., Schievano, E., Mammi, S., Wittelsberger, A., Chorev, M., & Peggion, E. (2006) · Padua Research Archive (University of Padova)
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Conformational and biological characterization of human parathyroid hormone hPTH(1–34) analogues containing β‐amino acid residues in positions 17–19
Schievano, E., Mammi, S., Carretta, E., Fiori, N., Corich, M., Bisello, A., Rosenblatt, M., Chorev, M., & Peggion, E. (2003) · Biopolymers · doi:10.1002/bip.10508 · Cited by 12 · see citing works
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Structure−Function Studies of Analogues of Parathyroid Hormone (PTH)-1−34 Containing β-Amino Acid Residues in Positions 11−13,
Peggion, E., Mammi, S., Schievano, E., Silvestri, L., Schiebler, L., Bisello, A., Rosenblatt, M., & Chorev, M. (2002) · Biochemistry · doi:10.1021/bi0200155 · Cited by 23 · see citing works
Self-citation

Authors: Barazza, A., Wittelsberger, A., Fiori, N., Schievano, E., Mammi, S., Toniolo, C., Alexander, J. M., Rosenblatt, M., Peggion, E., & Chorev, M.
Affiliations: Beth Israel Deaconess Medical Center (US)
Corresponding author: Peggion, E.
ORCID: Wittelsberger, A.
Schievano, E.
Mammi, S.
Toniolo, C.
Alexander, J.M.
Venue: The Journal of Peptide Research
Publisher: Wiley
Published: 2005-01
Volume: 65
Issue: 1
Pages: 23-35
ISSN: 1397-002X (ISSN-L)
DOI: 10.1111/j.1399-3011.2005.00207.x
OpenAlex: W1496691530
Cited by: 23
References: 56
Citations by year: 2024: 1 · 2019: 1 · 2017: 1 · 2015: 1 · 2014: 1 · 2013: 1
FWCI: 1.13
Type: journal article
Language: en
Open access: closed
Licence: onlinelibrary.wiley.com/termsAndConditions#vor (vor, 13 d)
Locations: Journal of Peptide Research (publishedVersion)
PubMed (publishedVersion)
Padua Research Archive (University of Padova) (submittedVersion)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Chemical Synthesis and Analysis
Life Sciences › Neuroscience › Cellular and Molecular Neuroscience › Neuropeptides and Animal Physiology
Health Sciences › Medicine › Nephrology › Parathyroid Disorders and Treatments
Keywords: parathyroid hormone, alpha-helix, alpha-aminoisobutyric acid, peptide analogues, biological activity, circular dichroism, trifluoroethanol
MeSH terms: Cyclic AMP, Amino Acid Sequence, Cell Line, Circular Dichroism, Humans, Ligands, Models, Molecular, Magnetic Resonance Spectroscopy, Oligopeptides, Parathyroid Hormone, Protein Structure, Secondary, Receptors, Parathyroid Hormone, Receptor, Parathyroid Hormone, Type 1

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Bioactive N‐terminal undecapeptides derived from parathyroid hormone: the role of α‐helicity*

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