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Photocured Films of Hyaluronic Acid Functionalized with Cyclodextrin

Photocured Films of Hyaluronic Acid Functionalized with Cyclodextrin. Scott A. Zawko 1 , Shalu Suri 2 , Prinon Hossain 2 , Quan Truong 2 , Christine E. Schmidt 1,2. 1 Department of Chemical Engineering 2 Department of Biomedical Engineering The University of Texas at Austin, Austin, TX. Drug.

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Photocured Films of Hyaluronic Acid Functionalized with Cyclodextrin

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  1. Photocured Films of Hyaluronic Acid Functionalized with Cyclodextrin Scott A. Zawko1, Shalu Suri2, Prinon Hossain2, Quan Truong2, Christine E. Schmidt1,2 1Department of Chemical Engineering 2Department of Biomedical Engineering The University of Texas at Austin, Austin, TX

  2. Drug Gel Uptake Release Goal: Hydrogel material that binds drug molecules Matrix: Hyaluronic Acid Functionalities: Cyclodextrin

  3. n O H Cyclodextrin O O • Host-Guest Inclusion Complexes • Increase solubilization • Decrease crystallization • Increase stability H O O H Composite Hydrogel Material Hyaluronic Acid High molecular weight High water content High porosity Biocompatible Biodegradable 7 MW = 5x105 – 2x106

  4. Ka ~ 105 M-1 b-cyclodextrin (n=7) a-cyclodextrin (n=6) HO + HO OH Adamantane I.D. ~ 6Å Cyclodextrin’s Structure Hydrophobic Interior Hydrophilic Exterior

  5. Ka ~ 103 M-1 + Hydrocortisone Cyclodextrin’s Structure Hydrocortisone Solubility (mM) b-Cyclodextrin (mM)

  6. + GMHA + Triethylamine Photoinitiator UV Light Leach, J.B. et al. (2003) Biotechnol Bioeng Methacryloyl Hyaluronic Acid Methacryloyl Cyclodextrin Photocrosslinked Hydrogels

  7. + GMHA Triethylamine Leach, J.B. et al. (2003) Biotechnol Bioeng Methacryloyl Hyaluronic Acid (GMHA)

  8. + GMHA Triethylamine Leach, J.B. et al. (2003) Biotechnol Bioeng Methacryloyl Hyaluronic Acid (GMHA)

  9. Possible steric hindrance Methacryloyl Cyclodextrin

  10. 3 MAbCD DS = 3.2 2 4 5 1 No unpolymerizable CD Low average DS Comparable DS 6 3 4 2 MAaCD DS = 3.6 5 1 Methacryloyl Cyclodextrin

  11. Hydrocortisone CD (mM): 0 1 3 5 Quantitation of MAbCD-Hydrocortisone Binding MAbCD: 1400 M-1 bCD: 5380 M-1

  12. Hyaluronic Acid Gels Hyaluronic Acid Films

  13. + I2959, UV Light bCD / HA aCD / HA 20% CD / 80% HA 0.5% w/v 33% CD / 67% HA 1.0% w/v 43% CD / 57% HA 1.5% w/v Swelling Ratio (PBS) 20 HA 33 43 Cyclodextrin (%w/w) Swelling of Hyaluronic Acid – Cyclodextrin Hydrogels Cyclodextrin Hyaluronic Acid CD / HA Hydrogel 2% w/v

  14. 43% bCD Hydrocortisone Gel Uptake Release 33% bCD Hydrocortisone Release (mg) 20% bCD 43% aCD 20% aCD HA Time (h) Hyaluronic Acid-Cyclodextrin Hydrogels: Hydrocortisone Uptake and Release

  15. Hydrocortisone Gel Uptake Release 1 HC : 8 MAbCD Hydrocortisone Release (mmol) 1 HC : 21 MAaCD Cyclodextrin (mmol) Hyaluronic Acid-Cyclodextrin Hydrogels: Hydrocortisone Uptake and Release

  16. HA 43% bCD 43% bCD Adamantane Hyaluronic Acid-Cyclodextrin Hydrogels: Hydrocortisone Uptake and Release Pre-incubation with Adamantane Carboxylic Acid Hydrocortisone Release (mmol)

  17. Hyaluronic Acid Gels Hyaluronic Acid Films

  18. Methacryloyl Hyaluronic Acid Films UV Air Dry GMHA + Photoinitiator

  19. Optimization of Photoinitiator 1 min UV Swelling Ratio (PBS) % Linear Expansion % Photoinitiator (w/w)

  20. Optimization of UV Exposure 5% PI Swelling Ratio (PBS) % Linear Expansion UV Exposure (min)

  21. Autoclave Sterilization of HA Films 30 minutes at 121 C and 15 psi Swelling Ratio (PBS) % Linear Expansion None Fast Slow Sterilization

  22. 500 mm Resistance to Cell Adhesion Human Dermal Fibroblasts HA Film TCPS

  23. 300 nm 100 mm Methacryloyl Hyaluronic Acid Films Properties Transparent Free Standing Highly Dense Low Swelling Biodegradable Non-cell adhesive Patternable Applications Post-surgical adhesion barriers Coatings

  24. Drug Gel Uptake Release Matrix: Hyaluronic Acid Functionalities: Cyclodextrin Goal: Hydrogel material that binds drug molecules

  25. Acknowledgements Funding Agencies NSF BES – 021744 NSF BES – 0500969 http://www.bme.utexas.edu/faculty/schmidt

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