Expanding the Scopes of Synthetics Organic and Polymer Chemistries. Utilization of the inherent stereochemcial and functional diversities of natural products
Event details
| Date | 10.10.2016 |
| Hour | 13:15 › 14:15 |
| Speaker | Prof. Karen Wooley, Texas A&M University - USA |
| Location | |
| Category | Conferences - Seminars |
A primary interest in the Wooley laboratory is the production of functional polymers from renewable sources that are capable of reverting to those natural products once their purpose has been served. The inherent stereochemical and functional diversities of natural products provide opportunities to expand the scopes and complexities of polymer materials, by utilizing fundamental synthetic organic chemistry approaches. This presentation will highlight synthetic strategies for the development of polymer materials, which can be produced by relatively simple approaches from complex polyhydroxyl natural products and can be made to exhibit a range of properties, based upon the monomeric building blocks and, typically, carbonate or phosphoester linkages. In one direction, polyhydroxyl natural products as the monomeric building blocks are combined with carbonates, found in common engineering materials, as the linkages, for which hydrolytic degradation is expected to produce the polyhydroxyl compound plus carbon dioxide. Five classes of natural monomers, D-glucose,1 quinic acid,2 ferulic acid,3 isosorbide4 and quercetin, are being evaluated for the construction of polycarbonates. The polyhydroxyl natural product monomers provide reactive hydroxyl groups for establishment of the polycarbonate backbones and their rigid cyclic core units together with the polar, hydrogen-bonding hydroxyl groups in the resulting polycarbonates are expected to lead to strong and tough materials for engineering, biomedical and other applications, where the combined properties and degradation potential can be utilized. In a second direction, phosphoester linkages are utilized, again borrowing from Nature, in the use of phosphoesters commonly found in biological macromolecules, such as DNA or RNA. Polyphosphoester-based block copolymers5 that can be produced rapidly and then undergo multiple chemical transformations and direct assembly in water into functional nanomaterials are serving as a platform for several directions toward their development as biomedical devices for the treatment of lung infections6 and osteosarcoma lung metastases.7 If time allows, recent developments toward the preparation of functional polypeptides and their assemblies8 will also be described. As this work is in progress, it is expected that the physical, mechanical, supramolecular assembly and stability properties will be tuned by the chemical compositions and structures, controlled by the advancement of synthetic methodologies by which to prepare such materials.
1 Mikami, K.; Lonnecker, A. T.; Gustafson, T. P.; Zinnel, N. F.; Pai, P.-J.; Russell, D. H.; Wooley, K. L. “Polycarbonates Derived from Glucose via an Organocatalytic Approach”, J. Am. Chem. Soc., 2013, 135(18), 6826-6829.
2 Besset, C. J.; Lonnecker, A. T.; Streff, J. M.; Wooley, K. L. “Polycarbonates from the Polyhydroxy Natural Product Quinic Acid”, Biomacromolecules, 2011, 12(7), 2512-2517.
3 (a) Noel, A.; Borguet, Y. P.; Raymond, J. E.; Wooley, K. L. “Poly(carbonate-amide)s derived from bio-based resources: Poly(ferulic acid-co-tyrosine)”, Macromolecules, 2014, 47, 2974-2983. (b) Noel, A.; Borguet, Y. P.; Raymond, J. E.; Wooley, K. L. “Poly(ferulic acid-co-tyrosine): Effect of the regiochemistry on the photophysical and physical properties, en route to biomedical applications”, Macromolecules, 2014, 47(20), 7109-7117
4 Kristufek, T. S.; Kristufek, S. L.; Link, L. A.; Weems, A. C.; Lonnecker, A. T.; Raymond, J. E.; Maitland, D. J.; Wooley, K. L. “Rapidly-cured Isosorbide Natural Product-based Cross-linked Polycarbonate Elastomers”, Polym. Chem., 2016, 7, 2639-2644.
5 (a) Zhang, S.; Zou, J.; Zhang, F.; Elsabahy, M.; Felder, S.; Zhu, J.; Pochan, D. J.; Wooley, K. L. “Rapid and versatile construction of diverse and functional nanostructures derived from a polyphosphoester-based biomimetic block copolymer system”, J. Am. Chem. Soc., 2012, 134(44), 18467-18474. (b) Elsabahy, M.; Zhang, S.; Zhang, F.; Deng, Z. J.; Lim, Y. H.; Wang, H.; Parsamian, P.; Hammond, P. T.; Wooley, K. L. “Surface Charges and Shell Crosslinks Each Play Significant Roles in Mediating Degradation, Biofouling, Cytotoxicity and Immunotoxicity for Polyphosphoester-based Nanoparticles”, Scientific Reports, 2013, 3 : 3313, 1-10. (c) Zou, J.; Zhang, F.; Zhang, S.; Pollack, S. F.; Elsabahy, M.; Fan, J.; Wooley, K. L. “Poly(ethylene oxide)-block-polyphosphoester-graft-paclitaxel Conjugates with Acid-labile Linkages as a pH-Sensitive and Functional Nanoscopic Platform for Paclitaxel Delivery”, Adv. Healthcare Mater., 2013, early view, DOI: 10.1002/adhm.201300235.
6 (a) Lim, Y. H.; Tiemann, K. M.; Heo, G. S.; Wagers, P. O.; Rezenom, Y. H.; Zhang, S.; Zhang, F.; Youngs, W. J.; Hunstad, D. A.; Wooley, K. L. “Preparation and in vitro Antimicrobial Activity of Silver-bearing Degradable Polymeric Nanoparticles of Polyphosphoester-block-Poly(L-lactide)”, ACS Nano, 2015, 9(2), 1995-2008. (b) Zhang, F.; Smolen, J. A.; Zhang, S.; Li, R.; Shah, P. N.; Cho, S.; Wang, H.; Raymond, J. E.; Cannon, C. L.; Wooley, K. L. “Degradable polyphosphoester-based silver-loaded nanoparticles as therapeutics for bacterial lung infections”, Nanoscale, 2015, 7, 2265-2270.
7 Zhang, F.; Zhang, S.; Pollack, S. F.; Li, R.; Gonzalez, A. M.; Fan, J.; Zou, J.; Leininger, S. E.; Pavia-Sanders, A.; Johnson, R.; Nelson, L. D.; Raymond, J. E.; Elsabahy, M.; Hughes, D. M. P.; Lenox, M. W.; Gustafson, T. P.; Wooley, K. L. “Improving Paclitaxel Delivery: In vitro and in vivo characterization of PEGylated polyphosphoester-based nanocarriers”, J. Am. Chem. Soc., 2015, 137, 2056-2066.
8 (a) Fan, J.; Zou, J.; He, X.; Zhang, F.; Zhang, S.; Raymond, J. E.; Wooley, K. L. “Tunable mechano-responsive organogels by ring-opening copolymerizations of N-carboxyanhydrides”, Chem. Sci., 2014, 5, 141-150. (b) He, X.; Fan, J.; Zhang, F.; Li, R.; Pollack, K. A.; Raymond, J. E.; Zou, J.; Wooley, K. L. “Multi-responsive Hydrogels Derived from the Self-assembly of Tethered Allyl-functionalized Racemic Oligopeptides”, J. Mater. Chem. B, 2014, 2(46), 8123-8130. (c) He, X.; Fan, J.; Zou, J.; Wooley, K. L. “Reversible Photo-patterning of Soft Conductive Materials via Spatially-defined Supramolecular Assembly”, Chem. Commun., 2016, 52, 8455-8458. Bio: Karen L. Wooley is the W. T. Doherty-Welch Chair in Chemistry and a University Distinguished Professor at Texas A&M University, where she holds appointments in the Departments of Chemistry, Chemical Engineering and Materials Science & Engineering. She also serves as Director of the Laboratory for Synthetic-Biologic Interactions. Research interests include the synthesis and characterization of degradable polymers derived from natural products, unique macromolecular architectures and complex polymer assemblies, and the design and development of well-defined nanostructured materials. The development of novel synthetic strategies, fundamental study of physicochemical and mechanical properties, and investigation of the functional performance of her materials in the diagnosis and treatment of disease, as non-toxic anti-biofouling or anti-icing coatings, as materials for microelectronics device applications, and as pollutant remediation systems are particular foci of her research activities. Her academic training included undergraduate study at Oregon State University (B.S., 1988) and graduate study under the direction of Professor Jean M. J. Fréchet at Cornell University (Ph.D., 1993). She began an academic career as an Assistant Professor of Chemistry at Washington University in St. Louis, Missouri, was promoted in 1999 to Full Professor with tenure, was installed as a James S. McDonnell Distinguished University Professor in Arts & Sciences in 2006, and in 2009, Karen relocated to Texas A&M University. Recent awards include the American Chemical Society Award in Polymer Chemistry (2014), Royal Society of Chemistry Centenary Prize (2014), Fellow of the Royal Society of Chemistry (2014), Honorary Fellow of the Chinese Chemical Society (2014), Oesper Award (2015), Fellow of the American Academy of Arts and Sciences (2015), and both Distinguished Research and Teaching Achievement Awards from the Texas A&M University Association of Former Students (2016). Karen currently serves as an Associate Editor for the Journal of the American Chemical Society, among many other advisory roles within the broader scientific community.
1 Mikami, K.; Lonnecker, A. T.; Gustafson, T. P.; Zinnel, N. F.; Pai, P.-J.; Russell, D. H.; Wooley, K. L. “Polycarbonates Derived from Glucose via an Organocatalytic Approach”, J. Am. Chem. Soc., 2013, 135(18), 6826-6829.
2 Besset, C. J.; Lonnecker, A. T.; Streff, J. M.; Wooley, K. L. “Polycarbonates from the Polyhydroxy Natural Product Quinic Acid”, Biomacromolecules, 2011, 12(7), 2512-2517.
3 (a) Noel, A.; Borguet, Y. P.; Raymond, J. E.; Wooley, K. L. “Poly(carbonate-amide)s derived from bio-based resources: Poly(ferulic acid-co-tyrosine)”, Macromolecules, 2014, 47, 2974-2983. (b) Noel, A.; Borguet, Y. P.; Raymond, J. E.; Wooley, K. L. “Poly(ferulic acid-co-tyrosine): Effect of the regiochemistry on the photophysical and physical properties, en route to biomedical applications”, Macromolecules, 2014, 47(20), 7109-7117
4 Kristufek, T. S.; Kristufek, S. L.; Link, L. A.; Weems, A. C.; Lonnecker, A. T.; Raymond, J. E.; Maitland, D. J.; Wooley, K. L. “Rapidly-cured Isosorbide Natural Product-based Cross-linked Polycarbonate Elastomers”, Polym. Chem., 2016, 7, 2639-2644.
5 (a) Zhang, S.; Zou, J.; Zhang, F.; Elsabahy, M.; Felder, S.; Zhu, J.; Pochan, D. J.; Wooley, K. L. “Rapid and versatile construction of diverse and functional nanostructures derived from a polyphosphoester-based biomimetic block copolymer system”, J. Am. Chem. Soc., 2012, 134(44), 18467-18474. (b) Elsabahy, M.; Zhang, S.; Zhang, F.; Deng, Z. J.; Lim, Y. H.; Wang, H.; Parsamian, P.; Hammond, P. T.; Wooley, K. L. “Surface Charges and Shell Crosslinks Each Play Significant Roles in Mediating Degradation, Biofouling, Cytotoxicity and Immunotoxicity for Polyphosphoester-based Nanoparticles”, Scientific Reports, 2013, 3 : 3313, 1-10. (c) Zou, J.; Zhang, F.; Zhang, S.; Pollack, S. F.; Elsabahy, M.; Fan, J.; Wooley, K. L. “Poly(ethylene oxide)-block-polyphosphoester-graft-paclitaxel Conjugates with Acid-labile Linkages as a pH-Sensitive and Functional Nanoscopic Platform for Paclitaxel Delivery”, Adv. Healthcare Mater., 2013, early view, DOI: 10.1002/adhm.201300235.
6 (a) Lim, Y. H.; Tiemann, K. M.; Heo, G. S.; Wagers, P. O.; Rezenom, Y. H.; Zhang, S.; Zhang, F.; Youngs, W. J.; Hunstad, D. A.; Wooley, K. L. “Preparation and in vitro Antimicrobial Activity of Silver-bearing Degradable Polymeric Nanoparticles of Polyphosphoester-block-Poly(L-lactide)”, ACS Nano, 2015, 9(2), 1995-2008. (b) Zhang, F.; Smolen, J. A.; Zhang, S.; Li, R.; Shah, P. N.; Cho, S.; Wang, H.; Raymond, J. E.; Cannon, C. L.; Wooley, K. L. “Degradable polyphosphoester-based silver-loaded nanoparticles as therapeutics for bacterial lung infections”, Nanoscale, 2015, 7, 2265-2270.
7 Zhang, F.; Zhang, S.; Pollack, S. F.; Li, R.; Gonzalez, A. M.; Fan, J.; Zou, J.; Leininger, S. E.; Pavia-Sanders, A.; Johnson, R.; Nelson, L. D.; Raymond, J. E.; Elsabahy, M.; Hughes, D. M. P.; Lenox, M. W.; Gustafson, T. P.; Wooley, K. L. “Improving Paclitaxel Delivery: In vitro and in vivo characterization of PEGylated polyphosphoester-based nanocarriers”, J. Am. Chem. Soc., 2015, 137, 2056-2066.
8 (a) Fan, J.; Zou, J.; He, X.; Zhang, F.; Zhang, S.; Raymond, J. E.; Wooley, K. L. “Tunable mechano-responsive organogels by ring-opening copolymerizations of N-carboxyanhydrides”, Chem. Sci., 2014, 5, 141-150. (b) He, X.; Fan, J.; Zhang, F.; Li, R.; Pollack, K. A.; Raymond, J. E.; Zou, J.; Wooley, K. L. “Multi-responsive Hydrogels Derived from the Self-assembly of Tethered Allyl-functionalized Racemic Oligopeptides”, J. Mater. Chem. B, 2014, 2(46), 8123-8130. (c) He, X.; Fan, J.; Zou, J.; Wooley, K. L. “Reversible Photo-patterning of Soft Conductive Materials via Spatially-defined Supramolecular Assembly”, Chem. Commun., 2016, 52, 8455-8458. Bio: Karen L. Wooley is the W. T. Doherty-Welch Chair in Chemistry and a University Distinguished Professor at Texas A&M University, where she holds appointments in the Departments of Chemistry, Chemical Engineering and Materials Science & Engineering. She also serves as Director of the Laboratory for Synthetic-Biologic Interactions. Research interests include the synthesis and characterization of degradable polymers derived from natural products, unique macromolecular architectures and complex polymer assemblies, and the design and development of well-defined nanostructured materials. The development of novel synthetic strategies, fundamental study of physicochemical and mechanical properties, and investigation of the functional performance of her materials in the diagnosis and treatment of disease, as non-toxic anti-biofouling or anti-icing coatings, as materials for microelectronics device applications, and as pollutant remediation systems are particular foci of her research activities. Her academic training included undergraduate study at Oregon State University (B.S., 1988) and graduate study under the direction of Professor Jean M. J. Fréchet at Cornell University (Ph.D., 1993). She began an academic career as an Assistant Professor of Chemistry at Washington University in St. Louis, Missouri, was promoted in 1999 to Full Professor with tenure, was installed as a James S. McDonnell Distinguished University Professor in Arts & Sciences in 2006, and in 2009, Karen relocated to Texas A&M University. Recent awards include the American Chemical Society Award in Polymer Chemistry (2014), Royal Society of Chemistry Centenary Prize (2014), Fellow of the Royal Society of Chemistry (2014), Honorary Fellow of the Chinese Chemical Society (2014), Oesper Award (2015), Fellow of the American Academy of Arts and Sciences (2015), and both Distinguished Research and Teaching Achievement Awards from the Texas A&M University Association of Former Students (2016). Karen currently serves as an Associate Editor for the Journal of the American Chemical Society, among many other advisory roles within the broader scientific community.
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