Skip to main content
Advertisement

Main menu

  • Home
  • Articles
    • Current Issue
    • Fast Forward
    • Latest Articles
    • Archive
  • Information
    • Instructions to Authors
    • Submit a Manuscript
    • FAQs
    • For Subscribers
    • Terms & Conditions of Use
    • Permissions
  • Editorial Board
  • Alerts
    • Alerts
    • RSS Feeds
  • Virtual Issues
  • Feedback
  • Other Publications
    • Drug Metabolism and Disposition
    • Journal of Pharmacology and Experimental Therapeutics
    • Molecular Pharmacology
    • Pharmacological Reviews
    • Pharmacology Research & Perspectives
    • ASPET

User menu

  • My alerts
  • Log in
  • My Cart

Search

  • Advanced search
Molecular Pharmacology
  • Other Publications
    • Drug Metabolism and Disposition
    • Journal of Pharmacology and Experimental Therapeutics
    • Molecular Pharmacology
    • Pharmacological Reviews
    • Pharmacology Research & Perspectives
    • ASPET
  • My alerts
  • Log in
  • My Cart
Molecular Pharmacology

Advanced Search

  • Home
  • Articles
    • Current Issue
    • Fast Forward
    • Latest Articles
    • Archive
  • Information
    • Instructions to Authors
    • Submit a Manuscript
    • FAQs
    • For Subscribers
    • Terms & Conditions of Use
    • Permissions
  • Editorial Board
  • Alerts
    • Alerts
    • RSS Feeds
  • Virtual Issues
  • Feedback
  • Visit molpharm on Facebook
  • Follow molpharm on Twitter
  • Follow molpharm on LinkedIn
Research ArticleArticle

Structure/Activity Relationships in Lysophosphatidic Acid: The 2-Hydroxyl Moiety

Kevin R. Lynch, Darrin W. Hopper, Steven J. Carlisle, John G. Catalano, Ming Zhang and Timothy L. Macdonald
Molecular Pharmacology July 1997, 52 (1) 75-81; DOI: https://doi.org/10.1124/mol.52.1.75
Kevin R. Lynch
Departments of 1 2
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Darrin W. Hopper
Departments of 1 2
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Steven J. Carlisle
Departments of 1 2
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
John G. Catalano
Departments of 1 2
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Ming Zhang
Departments of 1 2
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Timothy L. Macdonald
Departments of 1 2
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
  • Article
  • Figures & Data
  • Info & Metrics
  • eLetters
  • PDF
Loading

Abstract

Although lipid phosphoric acid mediators such as lysophosphatidic acid (LPA) are now recognized widely as intercellular signaling molecules, the medicinal chemistry of these mediators is poorly developed. With the goal of achieving a better understanding of the structure activity relationships in LPA, we have synthesized and tested a series of LPA analogs that lack the 2-hydroxyl moiety. Our series consisted of compounds with 2, 3, or 4 carbon diol or amino alcohol backbones and oleoyl or palmitoleoyl acyl groups. These molecules cannot be acylated further to form phosphatidic acids, nor do they have chiral centers. The rank order potency of these compounds in mobilization of calcium in MDA MB-231 cells suggested a maximum optimal chain length of 24–25 atoms. However, high potency for the inhibition of adenylyl cyclase in these cells was achieved only by one compound that also contained a dissociable proton five bond lengths from the phosphorus atom. That compound, N-oleoyl-2-hydroxyethyl-1-phosphate, was nearly equipotent to 1-oleoyl LPA in both assays. The striking mimicry of LPA by the ethanolamine-based compound and the presence of fatty acid amides in tissue prompts us to propose that phosphorylatedN-acyl ethanolamides occur naturally.

Footnotes

    • Received November 25, 1996.
    • Accepted March 28, 1997.
  • Send reprint requests to: Kevin R. Lynch, Ph.D., Department of Pharmacology, Box 448, University of Virginia Health Sciences Center, 1300 Jefferson Park Avenue, Charlottesville, VA 22908. E-mail:krl2z{at}virginia.edu

  • This work was supported by a grant from the National Institute of General Medical Sciences (R01-GM52722).

  • A preliminary report of this work was presented at the XVIth Washington (DC) International Spring Symposium “Frontiers in Bioactive Lipids ’96” in May, 1996.

  • The American Society for Pharmacology and Experimental Therapeutics
View Full Text

MolPharm articles become freely available 12 months after publication, and remain freely available for 5 years. 

Non-open access articles that fall outside this five year window are available only to institutional subscribers and current ASPET members, or through the article purchase feature at the bottom of the page. 

 

  • Click here for information on institutional subscriptions.
  • Click here for information on individual ASPET membership.

 

Log in using your username and password

Forgot your user name or password?

Purchase access

You may purchase access to this article. This will require you to create an account if you don't already have one.
PreviousNext
Back to top

In this issue

Molecular Pharmacology: 52 (1)
Molecular Pharmacology
Vol. 52, Issue 1
1 Jul 1997
  • Table of Contents
  • About the Cover
  • Index by author
Download PDF
Article Alerts
Sign In to Email Alerts with your Email Address
Email Article

Thank you for sharing this Molecular Pharmacology article.

NOTE: We request your email address only to inform the recipient that it was you who recommended this article, and that it is not junk mail. We do not retain these email addresses.

Enter multiple addresses on separate lines or separate them with commas.
Structure/Activity Relationships in Lysophosphatidic Acid: The 2-Hydroxyl Moiety
(Your Name) has forwarded a page to you from Molecular Pharmacology
(Your Name) thought you would be interested in this article in Molecular Pharmacology.
CAPTCHA
This question is for testing whether or not you are a human visitor and to prevent automated spam submissions.
Citation Tools
Research ArticleArticle

Structure/Activity Relationships in Lysophosphatidic Acid: The 2-Hydroxyl Moiety

Kevin R. Lynch, Darrin W. Hopper, Steven J. Carlisle, John G. Catalano, Ming Zhang and Timothy L. Macdonald
Molecular Pharmacology July 1, 1997, 52 (1) 75-81; DOI: https://doi.org/10.1124/mol.52.1.75

Citation Manager Formats

  • BibTeX
  • Bookends
  • EasyBib
  • EndNote (tagged)
  • EndNote 8 (xml)
  • Medlars
  • Mendeley
  • Papers
  • RefWorks Tagged
  • Ref Manager
  • RIS
  • Zotero
Share
Research ArticleArticle

Structure/Activity Relationships in Lysophosphatidic Acid: The 2-Hydroxyl Moiety

Kevin R. Lynch, Darrin W. Hopper, Steven J. Carlisle, John G. Catalano, Ming Zhang and Timothy L. Macdonald
Molecular Pharmacology July 1, 1997, 52 (1) 75-81; DOI: https://doi.org/10.1124/mol.52.1.75
del.icio.us logo Digg logo Reddit logo Twitter logo CiteULike logo Facebook logo Google logo Mendeley logo
  • Tweet Widget
  • Facebook Like
  • Google Plus One

Jump to section

  • Article
    • Abstract
    • Experimental Procedures
    • Results
    • Discussion
    • Acknowledgments
    • Footnotes
    • Abbreviations
    • References
  • Figures & Data
  • Info & Metrics
  • eLetters
  • PDF

Related Articles

Cited By...

More in this TOC Section

  • GABAAR Molecular Identity in Oligodendrocytes
  • Editing TOP2α Intron-19 5′ SS Circumvents Drug Resistance
  • SerpinA3N and drug induced liver injury
Show more Article

Similar Articles

  • Home
  • Alerts
Facebook   Twitter   LinkedIn   RSS

Navigate

  • Current Issue
  • Fast Forward by date
  • Fast Forward by section
  • Latest Articles
  • Archive
  • Search for Articles
  • Feedback
  • ASPET

More Information

  • About Molecular Pharmacology
  • Editorial Board
  • Instructions to Authors
  • Submit a Manuscript
  • Customized Alerts
  • RSS Feeds
  • Subscriptions
  • Permissions
  • Terms & Conditions of Use

ASPET's Other Journals

  • Drug Metabolism and Disposition
  • Journal of Pharmacology and Experimental Therapeutics
  • Pharmacological Reviews
  • Pharmacology Research & Perspectives
ISSN 1521-0111 (Online)

Copyright © 2021 by the American Society for Pharmacology and Experimental Therapeutics