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Inhibition of Cell Adhesion to Fibronectin by Oligopeptide-Substituted Polynorbornenes

Maynard, Heather D. and Okada, Sheldon Y. and Grubbs, Robert H. (2001) Inhibition of Cell Adhesion to Fibronectin by Oligopeptide-Substituted Polynorbornenes. Journal of the American Chemical Society, 123 (7). pp. 1275-1279. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170404-101354154

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Abstract

Polynorbornenes substituted with two different peptide sequences from the RGD-containing integrin cell-binding domain of fibronectin are potent inhibitors of human foreskin fibroblast cell adhesion to fibronectin-coated surfaces. Ring-opening metathesis polymerization (ROMP) using Ru═CHPh(Cl)_2(PCy_3)(DHIMes) (1) as an initiator produced polymers substituted with GRGDS and PHSRN peptide sequences. The inhibitory activity was quantified for these polymers and compared to the free peptides and GRGES-containing controls. A homopolymer substituted with GRGDS peptides was significantly more active than the free GRGDS peptide (IC_(50) of 0.18 ± 0.03 and 1.33 ± 0.20 mM respectively), and the copolymer containing both GRGDS and PHSRN is the most potent inhibitor (IC_(50) of 0.04 ± 0.01 mM). These results demonstrate that significant enhancements of observed biological activity can be obtained from polymeric materials containing more than one type of multivalent ligand and that ROMP is a useful method to synthesize such well-defined copolymers.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja003305mDOIArticle
http://pubs.acs.org/doi/full/10.1021/ja003305mPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja003305mRelated ItemSupporting Information
ORCID:
AuthorORCID
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2001 American Chemical Society. Received 7 September 2000. Published online 26 January 2001. Published in print 1 February 2001. We thank Bayer Corporation and the Air Force Office of Sponsored Research (Grant F49620-97-1-0014) for funding this research. Professor David Tirrell is gratefully acknowledged for allowing us to use his cell culture room and aqueous GPC. Sarah Heilshorn, Dr. Natalie Winblade, and Dr. Jason Schense are appreciated for their many helpful discussions.
Funders:
Funding AgencyGrant Number
Bayer CorporationUNSPECIFIED
Air Force Office of Scientific Research (AFOSR)F49620-97-1-0014
Issue or Number:7
Record Number:CaltechAUTHORS:20170404-101354154
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170404-101354154
Official Citation:Inhibition of Cell Adhesion to Fibronectin by Oligopeptide-Substituted Polynorbornenes Heather D. Maynard, Sheldon Y. Okada, and Robert H. Grubbs Journal of the American Chemical Society 2001 123 (7), 1275-1279 DOI: 10.1021/ja003305m
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:75684
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:04 Apr 2017 18:53
Last Modified:03 Oct 2019 16:52

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