1. Field of the Invention
The present subject matter relates to polymers that depolymerize autonomously in response to specific signals. Methods of use of the polymers and articles made from or including those articles are also included herein.
2. Background of the Related Art
Cells exhibit diverse responses to trace levels of external chemical and physical signals. Their response characteristics are sophisticated, sensitive, and selective, and the ability to mimic such properties with synthetic materials has been a long sought after goal in materials chemistry.1 Materials with “life-like” qualities should be useful as smart coatings, textiles, adhesives, bandages, packaging, plastics, as well as in many other applications.
Recent advances in materials chemistry have provided macroscopic materials that begin to emulate some of these basic behaviors. For example, some macroscopic materials move in response to applied chemical and physical signals, repair themselves when subjected to mechanical stresses, or change wetting properties as a function of temperature. Other macroscopic materials have shape memory, and will adopt their original shapes after being perturbed by external forces. In other cases, the physical state of a material changes (i.e., solution⇄gel) upon exposure to pH gradients (e.g., pH-responsive hydrogels), variations in temperature, small molecules (e.g., NO-responsive hydrogels), or light.
In these examples, the materials typically exhibit a single response to a single type of signal. Living systems, in contrast, are capable of responding selectively to many signals (both chemical and physical), and providing unique responses to each signal. Living systems also exhibit remarkably amplified responses to an applied signal. Most responsive materials that are currently available cannot behave with such sensitivity and specificity.
One or more of the following documents may be useful in understanding one or more embodiments of the invention. Inclusion of a document herein is not an admission that it is prior art or that it adversely affects the patentability of any claim of this application. The documents are incorporated by reference as if rewritten herein. Where this specification differs from one or more of the cited documents, this specification controls. Documents of interest include Polaske, et al., Org. Let. 2010, 12 (21), 4944-47; McGrath, D. V., Molec. Pharm. 2005, 2(4), 253-63; Li, et al., J. Am. Chem. Soc. 2003, 125, 10516-17; Szalai, et al., J. Am. Chem. Soc. 2003, 125, 15688-89; Knoll, et al., Adv. Mater. 2010, 22, 3361-65; Coulembier, et al., Macromol., 2010, 43, 572-74; Ortiz, et al., J. Org. Chem. 2010, 75, 6154-62; Lin, et al., Chem. Commun. 2009, 803-05; de Montigny, et al., Anal. Chem. 1987, 59, 1096-1101; Benson, et al., Proc. Nat. Acad. Sci. USA, 1975, 72(2), 619-22; Zhang, et al., Macromol., 2007, 40, 4154-58; Szali, et al., Tetrahedron, 2004, 60, 7261-7266; U.S. Pat. Nos. 4,734,481 and 4,820,829, to Steinmann; U.S. Pat. No. 7,625,764, to Stayton, et al.; International Patent Application Publication No. WO2008/053479, to Shabat, et al.; Tsuda, et al., J. Polymer Sci., 1997, 35, 77-89; Shabat, et al., Chem. Eur. J., 2004, 10, 2626-34; DeWit, et al., J. Am. Chem. Soc., 2009, 131, 18327-34; Esser-Kahn, et al., J. Am. Chem. Soc. 2010, 132, 10266-68; Knoll, et al., Adv. Mater. 2010, 22, 3361-3365; Ortiz, et al., J. Org. Chem., 2010, 75, 6154-62; Lahann, J.; Langer, R. MRS Bulletin 2005, 30, 185-188; Mendes, P. M. Chem. Soc. Rev. 2008, 37, 2512-2529; Tokarev, I.; Minko, S. Soft Matter. 2009, 5, 511-524; Yerushalmi, R.; Scherz, A.; van der Boom, M. E.; Kraatz, H.-B. J. Mater. Chem. 2005, 15, 4480-1487. Stuart, M. A. C.; et al. Nat. Mater. 2010, 9, 101-113. Yoshida, M.; Lahann, J. ACS Nano 2008, 2, 1101-1107; Grzybowski, B. A.; Whitesides, G. M. Science 2002, 296, 718-721. Zhang, et al., Nano Lett, 2009, 9, 3663-3667; Mallouk, T. E.; Sen, A. Sci. Am. 2009, 300, 72-77. (d) Ismagilov, R. F.; Schwartz, A.; Bowden, N.; Whitesides, G. M. Angew. Chem. Int. Ed. 2001, 41, 652-654. (e) Mano, N.; Heller, A. J. Am. Chem. Soc., 2005, 127, 11574-11575. (f) Pantarotto, D.; Browne, W. R.; Feringa, B. L. Chem. Commun., 2008, 1533-1535; Whites, S. R., et al., Nature 2001, 409, 794-797; Urban, M. W. Prog. Polym. Sci. 2009, 34, 679-687. (c) Murphy, E. B.; Wudl, F. Prog. Polym. Sci. 2010, 35, 223-251; Wool, R. P. Soft Matter. 2008, 4, 400-418; Kim, J.; Yoon, J.; Hayward, R. C. Nature Mat. 2009, 9, 159-164; Motornov, M., et al., Langmuir 2003, 19, 8077-8085; Rogers, C. Sci. Am. 1995, 154-157; Hu, J., Shape Memory Polymers and Textiles, CRC Press, 2007; Bellin, I.; Kelch, S.; Langer, R.; Lendlein, A. Proc. Natl. Acad. Sci., U.S.A. 2006, 103, 18043-18047; Lendlein, A.; Langer, R. Science 2002, 296, 1673-1676; Lendlein, A.; Jiang, H.; Jünger, O.; Langer, R. Nature 2005, 434, 879-882; Jaguar-Grodzinski, J. Polym. Adv. Technol. 2010, 21, 27-47; Schild, H. G. Prog. Polym. Sci. 1992, 17, 163-249; Chen, J.; McNeil, A. J. J. Am. Chem. Soc. 2008, 130, 16496-16497; Yu, Y.; Nakano, M.; Ikeda, T. Nature 2003, 425, 145; Li, M.-H.; Keller, P.; Li, B.; Wang, X.; Brunet, M. Adv. Mater. 2003, 15, 569-572; Liu, J., et al., Adv. Mater. 2008, 20, 2508-2511; Qiu, Z.; Yu, H.; Li, J.; Wang, Y.; Zhang, Y. Chem. Commun. 2009, 3342-3344; Krieg, E.; Shirman, E.; Weissman, H.; Shimoni, E.; Wolf, S. G.; Pinkas, I.; Rybtchinski, B. J. Am. Chem. Soc. 2009, 131, 14365-14373; Komatsu, H., et al., J. Am. Chem. Soc. 2009, 131, 5580-5585; Ito, H.; Willson, C. G. Polym. Eng. Sci. 1983, 23, 1012-1018; Aso, C.; Tagami, S.; Kunitake, T. J. Polym. Sci., Part A: Polym. Chem. 1969, 7, 497-511; Ito, H. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 3863-3870; Köstler, S.; Zechner, B.; Trathnigg, B.; Fasl, H.; Kern, W.; Ribitsch, V. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 1499-1509; Tsuda, M.; Hata, M.; Nishida, R.; Oikawa, S. J. Photopolym. Sci. Technol. 1993, 6, 491-494; MacDonald, S. A.; Willson, C. G.; Fréchet, J. M. J. Acc. Chem. Res. 1994, 27, 151-158; Amir, R. J., et al., Angew. Chem. Int. Ed. 2003, 42, 4494-4499; de Groot, F. M. H.; Albrecht, C.; Koekkoek, R.; Beusker, P. H.; Scheeren, H. W. Angew. Chem. Int. Ed. 2003, 42, 4490-4494; Sagi, A.; Weinstain, R.; Karton, N.; Shabat, D. J. Am. Chem. Soc. 2008, 130, 5434-5435; Weinstain, R.; Baran, P. S.; Shabat, D. Bioconjugate. Chem. 2009, 20, 1783-1791; DeWitt, M. A.; Gillies, E. R. J. Am. Chem. Soc. 2009, 131, 18327-18334; Sella, E.; Lubelski, A.; Klafter, J.; Shabat, D. J. Am. Chem. Soc. 2010, 132, 3945-3952; Nakayama, K.; Uoto, K.; Higashi, K.; Soga, T.; Kusama, T. Chem. Pharm. Bull. 1992, 40, 1718-1720; Hayakawa, Y.; Kato, H.; Uchiyama, M.; Kajino, H.; Noyori, R. J. Org. Chem. 1986, 51, 2400-2402; and Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
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USPTO Backgrounds