Synthesis and Characterization of Poly(antioxidant β-amino esters) for the Modulation of Cellular Oxidative Stress

Monday, November 8, 2010: 10:00 AM
Grand Ballroom F (Salt Palace Convention Center)
Paritosh Wattamwar, Dipti Biswal, J. Zach Hilt and Thomas D. Dziubla, Chemical and Materials Engineering, University of Kentucky, Lexington, KY

Oxidative stress is a cellular state characterized by an excess production of reactive oxygen species (e.g., superoxide, hydrogen peroxide) in comparison to natural antioxidant systems. By controlling the oxidative stress levels, it is possible to tune cell differentiation and expression[1, 2]. If there is a mean to control sustained delivery of these antioxidants at desired concentrations, it may be possible to use oxidative stress status to tune cell response for tissue engineering applications. In a previous study, we had demonstrated that poly(trolox), polymer of trolox (a water soluble analogue of Vitamin E), can attenuate oxidative stress injury in vitro[3]. However, the poly(phenol ester) chemistry of poly(trolox) resulted in a slowly degrading polymer limiting its application. In this work, we polymerized antioxidants using β-amino ester chemistry. Previous studies have shown that poly(β-amino esters) are hydrolytically degradable, their degradation is pH sensitive, and they can be further polymerized into hydrogel form[4]. Starting with several antioxidant monomers, poly(antioxidant β-amino esters) were synthesized and characterized for their degradation rate and antioxidant activity. Effect of the degradation of poly(antioxidant β-amino esters) on cytotoxicity and oxidative stress levels in the cells was also studied.

References: [1] K. M. Choi, Y. K. Seo, H. H. Yoon, K. Y. Song, S. Y. Kwon, H. S. Lee, J. K. Park, J Biosci Bioeng 2008, 105, 586. [2] K. J. Lampe, R. M. Namba, T. R. Silverman, K. B. Bjugstad, M. J. Mahoney, Biotechnol Bioeng 2009, 103, 1214. [3] P. P. Wattamwar, Y. Q. Mo, R. Wan, R. Palli, Q. W. Zhang, T. D. Dziubla, Advanced Functional Materials 2010, 20, 147. [4] D. G. Anderson, C. A. Tweedie, N. Hossain, S. M. Navarro, D. M. Brey, K. J. Van Vliet, R. Langer, J. A. Burdick, Advanced Materials 2006, 18, 2614.


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