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Published August 2012 | Accepted Version + Published + Supplemental Material
Journal Article Open

Synthesis and Cell Adhesive Properties of Linear and Cyclic RGD Functionalized Polynorbornene Thin Films


Described herein is the efficient synthesis and evaluation of bioactive arginine-glycine-aspartic acid (RGD) functionalized polynorbornene-based materials for cell adhesion and spreading. Polynorbornenes containing either linear or cyclic RGD peptides were synthesized by ring-opening metathesis polymerization (ROMP) using the well-defined ruthenium initiator [(H_(2)IMes)(pyr)_(2)(Cl)_(2)Ru═CHPh]. The random copolymerization of three separate norbornene monomers allowed for the incorporation of water-soluble polyethylene glycol (PEG) moieties, RGD cell recognition motifs, and primary amines for postpolymerization cross-linking. Following polymer synthesis, thin-film hydrogels were formed by cross-linking with bis(sulfosuccinimidyl) suberate (BS^3), and the ability of these materials to support human umbilical vein endothelial cell (HUVEC) adhesion and spreading was evaluated and quantified. When compared to control polymers containing either no peptide or a scrambled RDG peptide, polymers with linear or cyclic RGD at varying concentrations displayed excellent cell adhesive properties in both serum-supplemented and serum-free media. Polymers with cyclic RGD side chains maintained cell adhesion and exhibited comparable integrin binding at a 100-fold lower concentration than those carrying linear RGD peptides. The precise control of monomer incorporation enabled by ROMP allows for quantification of the impact of RGD structure and concentration on cell adhesion and spreading. The results presented here will serve to guide future efforts for the design of RGD functionalized materials with applications in surgery, tissue engineering, and regenerative medicine.

Additional Information

© 2012 American Chemical Society. Received: May 21, 2012; Revised: July 5, 2012; Published: July 11, 2012. We thank Professor Chin-Lin Guo for use of his inverted epifluorescence microscope, and Mr. Jiun-Yann Yu for assistance with the microscope. Ms. Chithra Krishnamurthy is thanked for helpful discussions. This research was supported by the National Institutes of Health (5R01-GM31332, F32 HL091440), the NSF Materials Research Science and Engineering Center at Caltech (DMR 0520565), the Beckman Institute at Caltech (postdoctoral fellowship to R.C.K.), and grants from the California Institute for Regenerative Medicine. Materia, Inc. is thanked for its donation of metathesis catalysts.

Attached Files

Published - bm300795y.pdf

Accepted Version - nihms397370.pdf

Supplemental Material - bm300795y_si_001.pdf


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August 19, 2023
October 19, 2023