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Thymine Polymers

Thymine Polymers. Amy S. Cannon, Ph.D. Center for Green Chemistry University of Massachusetts Lowell. NonCovalent Derivatization. Educational Research. Bioinspired Polymers. Medicinal Chemistry. Reaction Design. Ambient Metal Oxide Semiconductors. Bioinspiration. Green Chemistry and

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Thymine Polymers

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  1. Thymine Polymers Amy S. Cannon, Ph.D. Center for Green Chemistry University of Massachusetts Lowell

  2. NonCovalent Derivatization Educational Research Bioinspired Polymers Medicinal Chemistry Reaction Design Ambient Metal Oxide Semiconductors Bioinspiration Green Chemistry and Sustainable Materials Molecular Recognition and Self-Assembly

  3. Bioinspired Photopolymers Chemistry au Naturel Chemists aim to mimic natural systems with the hope of developing more-efficient chemical processes that are also less harmful to the environment. February 12 2005

  4. Pustular Psoriasis

  5. PUVA Phototherapy

  6. Psoriasis – What’s Happening? Normal Psoriatic

  7. Thymine in DNA

  8. Photodimerization of Thymine in DNA *Diagram taken from Principles of Biochemistry, 2nd Edition, Horton, et al.

  9. Physiological repair mechanisms

  10. Polymerization Site p-Stacking Site Photodimerization Site Triple H-Bonding Site Derivatization Site pKa ~ 9 Vinylbenzyl Thymine

  11. Organic Soluble Polymers Styrene Methacrylate

  12. Water Soluble Polymers Cationic Anionic

  13. Electrostatic Affinity Kiarie, C.; Bianchini, J.; Trakhtenberg, S.; Warner, J.C. Methylene Blue Adsorption on Thymine Based Polyvinylphenylsulfonate FilmsJ. Macromol. Sci. A, 2005, 42(11), 1489-1496

  14. Food Color Dyes FD&C Yellow No. 5 FD&C Green No. 3 FD&C Red No. 40 FD&C Blue No. 1 FD&C Yellow No. 6 FD&C Red No. 3

  15. Polymer Crosslinking PCT Int. Appl. WO 9,729,405. August 14, 1997. US Patent 5,705,312. January 6, 1998. US Patent 5,708,106. January 13, 1998. US Patent 5,741,630. April 21, 1998. US Patent 5,750,463. May 12, 1998. US Patent 5,750,464. May 12, 1998.

  16. APPLICATION: Enzymatic Reversal “Enzymatic Reversal of Polymeric Thymine Photocrosslinking with E. coli DNA Photolyase” Whitfield, Justin; Morelli, Alessandra and Warner, John C., J. Macr. Sci.2005A42 1541-1546. "Methods of solubilizing and recycling biodegradable polymers containing photoreactive moieties using irradiation", Warner, John C.; Morelli, Alessandra; Ku, Man-Ching U.S. Pat. Appl. Publ. 2003, 4 pp. US 2003224497.

  17. (a) (b) SEM of photoresist film showing region of removal at (a) 1000X and (b) 40X

  18. Applications • Photoresist polymers • Controlled release • Hair and fabric toning and shaping • Templated Conductive polymers • Antimicrobial surfaces

  19. Conventional Photoresists Acrylates and Acrylamides… Trapped Residues

  20. Environmentally Benign Photoresists Nontoxic, Water Soluble… No “Trapped” Reactants

  21. APPLICATION: Photoresists Kindstrand, L.L. Warner, J.C. Thymine-containing styrene polymers as environmentally benign photoresists in Biopolymers, Volume 9, Eds.: S. Matsumura and A. Steinbuechel Wiley-VCH Verlag GmbH, Weinheim, Germany 2003, pp 165-174 Warner, J. C. Environmentally Benign Photopolymers Based on DNA MimicsARCHIPOL 2005: III Argentine-Chilean Polymer Symposium, Cordoba, Argentina, December 4-7, 2005, 13. Trakhtenberg, S.; Warner, J. C.; Nagarajana, Ramaswamy; Bruno, Ferdinando F.; Samuelson, Lynne A.; Kumar, Jayant Spectroscopic and Microscopic Analysis of Photocrosslinked Vinylbenzylthymine (VBT) Copolymers for Photoresist ApplicationsChem. Mater. 2006In Press..

  22. Irradiation Response Yu, C.; Trakhtenberg, S.; Cain, T. E.; Warner, J. C. Effect of Dye Additives on Photodimerization of Thymine Pendant Groups in Water-Soluble Photoresist PolymersJournal of Polymers and the Environment. 2006In Press.

  23. Applications • Photoresist polymers • Controlled release • Hair and fabric toning and shaping • Templated Conductive polymers • Antimicrobial surfaces

  24. 3 2 1 25% PVA, 75% VBT, 2 micron 10% PVA, 90% VBT, 2 micron 48% PVA, 48% VBT, 4% Dye 2 micron PET Film APPLICATION: Controlled Release

  25. Seconds of immersion in water. 30 Time time time 25 20 15 10 5

  26. Diffusion Rate as a function of UV Exposure Absorbance UV Exposure (Min)

  27. Applications • Photoresist polymers • Controlled release • Hair and fabric toning and shaping • Templated Conductive polymers • Antimicrobial surfaces

  28. APPLICATION: Hair and Fabric Curling and Toning “Photoreactive Polymers and Devices for use in Hair Treatments”, Cannon, Amy S.; Raudys, Jennifer; Undurti, Arundhati; Warner, John C. PCT Int. Appl. 2004, 23pp WO 2004058187.

  29. Applications • Photoresist polymers • Controlled release • Hair and fabric toning and shaping • Templated Conductive polymers • Antimicrobial surfaces

  30. Enzyme Horseradish Peroxidase + Aniline APPLICATION: Templated Conductive Polymers “Photocrosslinked Immobilization of Polyelectrolytes for Enzymatic Construction of Conductive Nanocomposites” Trakhtenberg, Sofia; Hangun-Balkir, Yelda; Warner, John C.; Bruno, Ferdinando; Kumar, Jayant; Nagarajan, Ramaswamy; Samuelson, Lynne A. J. Am. Chem. Soc.2005127, 9100-9104

  31. 1 cm “Photocrosslinked Immobilization of Polyelectrolytes for Enzymatic Construction of Conductive Nanocomposites” Trakhtenberg, Sofia; Hangun-Balkir, Yelda; Warner, John C.; Bruno, Ferdinando; Kumar, Jayant; Nagarajan, Ramaswamy; Samuelson, Lynne A. J. Am. Chem. Soc.2005127, 9100-9104

  32. Applications • Photoresist polymers • Controlled release • Hair and fabric toning and shaping • Templated Conductive polymers • Antimicrobial surfaces

  33. APPLICATION: Antimicrobial surfacesE- Coli Bacterial growth Control plate : no polymer Coated plate : no bacterial growth El-Hayek, R.; Warner, J. C. Bacteriostatic Polymer Film ImmobilizationJ. Bio. Mat. Res. 2006 In Press.. “Immobilized Antimicrobial Films”, El-Hayek, Rami; Mullin, Steve; Warner, John C. Patent Disclosure Filed with UML CVIP 2005.

  34. Current and Future Directions • Structural integrity of polymers • Biodegradable/renewable polymers • Enzymatic reversal – extremophiles • Textiles

  35. Acknowledgements Jason Bianchini Kevin Dye Rami El Hayek Laura Ingalls Cecilia Kiarie Justin Whitfield Funding: SAPPI Toxics Use Reduction Institute Dr. Roger Boggs Dr. Yelda Hangun-Balkir Dr. Jayant Kumar Dr. Ramaswamy Nagarajan Dr. Kei Saito Dr. Lynne Samuelson Dr. Sofia Trakhtenberg Dr. John Warner

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