logo
My Activity

Recently Viewed

You have not visited any articles yet, Please visit some articles to see contents here.
CONTENT TYPES

Design and Synthesis of Potent Cystine-Free Cyclic Hexapeptide Agonists at the Human Urotensin Receptor

View Author Information
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, MDS Pharma Services, Bothell, Washington 98021, and MDS Pharma Services, Taipei, Taiwan
Cite this:Org. Lett.2006891799-1802
Publication Date (Web):March 29, 2006
ericyue.info/10.1021/ol060278h
Copyright © 2006 American Chemical Society
Article Views
299
Altmetric
-
Citations
LEARN ABOUT THESE METRICS

Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

Citations are the number of other articles citing this article, calculated by Crossref and updated daily.

The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on

Read OnlinePDF (108 KB)
Supporting Info (2)»

Abstract

Abstract Image

Cyclic hexapeptides, incorporating a dipeptide unit in place of the disulfide bond found in urotensin, were prepared and screened at the human urotensin receptor. The bridging dipeptide unit was found to influence dramatically the affinity for the urotensin receptor. Alanyl-N-methylalanyl and alanylprolyl dipeptide bridges failed to afford active ligands, while the alanyl-alanyl unit yielded a ligand with submicromolar affinity for the urotensin receptor. Further development led to a hexapeptide agonist with nanomolar affinity (2.8 nM).

Supporting Information Available

ARTICLE SECTIONS
Jump To

Experimental details and characterization data are provided for 2 and 811. This material is available free of charge via the Internet at .

Cited By


This article is cited by 13 publications.

  1. Elke Haensele, Nawel Mele, Marija Miljak, Christopher M. Read, David C. Whitley, Lee Banting, Carla Delépée, Jana Sopkova-de Oliveira Santos, Alban Lepailleur, Ronan Bureau, Jonathan W. Essex, and Timothy Clark . Conformation and Dynamics of Human Urotensin II and Urotensin Related Peptide in Aqueous Solution. Journal of Chemical Information and Modeling 2017, 57 (2) , 298-310. DOI: 10.1021/acs.jcim.6b00706.
  2. Jessica M. Smith, John R. Frost, and Rudi Fasan . Emerging Strategies to Access Peptide Macrocycles from Genetically Encoded Polypeptides. The Journal of Organic Chemistry 2013, 78 (8) , 3525-3531. DOI: 10.1021/jo400119s.
  3. Bruce E. Maryanoff and William A. Kinney . Urotensin-II Receptor Modulators as Potential Drugs. Journal of Medicinal Chemistry 2010, 53 (7) , 2695-2708. DOI: 10.1021/jm901294u.
  4. Bruce E. Maryanoff and William A. Kinney . Urotensin-II Receptor Modulators as Potential Drugs. Journal of Medicinal Chemistry , 0 (proofing) DOI: 10.1021/[email protected]
  5. Francesca Vitali, Rudi Fasan. . 2017,,, 155. DOI: 10.1002/9781119092599.ch7.
  6. Salvatore Pacifico, Aidan Kerckhoffs, Andrew J. Fallow, Rachel E. Foreman, Remo Guerrini, John McDonald, David G. Lambert, Andrew G. Jamieson. Urotensin-II peptidomimetic incorporating a non-reducible 1,5-triazole disulfide bond reveals a pseudo-irreversible covalent binding mechanism to the urotensin G-protein coupled receptor. Organic & Biomolecular Chemistry 2017, 15 (21) , 4704-4710. DOI: 10.1039/C7OB00959C.
  7. Francesco Merlino, Salvatore Di Maro, Ali Munaim Yousif, Michele Caraglia, Paolo Grieco. Urotensin-II Ligands: An Overview from Peptide to Nonpeptide Structures. Journal of Amino Acids 2013, 2013, 1-15. DOI: 10.1155/2013/979016.
  8. Justin S. Quartararo, Pianpian Wu, Joshua A. Kritzer. Peptide Bicycles that Inhibit the Grb2 SH2 Domain. ChemBioChem 2012, 13 (10) , 1490-1496. DOI: 10.1002/cbic.201200175.
  9. Fredrik Lehmann, Erika A. Currier, Roger Olsson, Jian-Nong Ma, Ethan S. Burstein, Uli Hacksell, Kristina Luthman. Optimization of isochromanone based urotensin II receptor agonists. Bioorganic & Medicinal Chemistry 2010, 18 (13) , 4844-4854. DOI: 10.1016/j.bmc.2010.04.041.
  10. Hubert Vaudry, Jean-Claude Do Rego, Jean-Claude Le Mevel, David Chatenet, Hervé Tostivint, Alain Fournier, Marie-Christine Tonon, Georges Pelletier, J. Michael Conlon, Jérôme Leprince. Urotensin II, from fish to human. Annals of the New York Academy of Sciences 2010, 1200 (1) , 53-66. DOI: 10.1111/j.1749-6632.2010.05514.x.
  11. Veronique Maes, Dirk Tourwé. Aspects of Peptidomimetics. 2009,,, 49-131. DOI: 10.1002/9780470749708.ch3.
  12. Christopher J. Chapman, Jonathan D. Hargrave, Gerwyn Bish, Christopher G. Frost. Peptide modification through site-selective residue interconversion: application of the rhodium-catalysed 1,4-addition of aryl siloxanes and boronates. Tetrahedron 2008, 64 (40) , 9528-9539. DOI: 10.1016/j.tet.2008.07.067.
  13. Shane Foister, Laurie L. Taylor, Jin-Jye Feng, Wen-Long Chen, Atsui Lin, Fong-Chi Cheng, Amos B. III Smith, Ralph Hirschmann. Design and Synthesis of Potent Cystine-Free Cyclic Hexapeptide Agonists at the Human Urotensin Receptor.. ChemInform 2006, 37 (33) DOI: 10.1002/chin.200633202.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

OOPS

You have to login with your ACS ID befor you can login with your Mendeley account.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses s to improve your user experience. By continuing to use the site, you are accepting our use of s. .

CONTINUE