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Biodegradable polymer coating for controlled release of hydrophobic functional molecules from cotton fabrics

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Abstract

Despite major advances in polymer chemistry, cotton still remains the principal textile component in the global pharmaceutical industry owing to its intrinsic strength, thermal stability, biocompatibility, and pleasant texture. Nevertheless, the hydrophilic nature of cotton requires the development of strategies for the incorporation of hydrophobic functional molecules into the fabric for controlled-release applications. To address this issue, we designed biodegradable crosslinked poly(β-amino ester) (PBAE) coatings as reservoirs for the incorporation of small hydrophobic molecules and studied their release profiles under physiological conditions. Two PBAEs with different hydrophobic and degradation properties were prepared and crosslinked to cotton fabrics in the presence of azulene, which served as a model hydrophobic, active material. Optimization of the crosslinking process in terms of UV curing time and the amount of solvent revealed that curing time of 15 min using 0.5 mL of chloroform was the optimal crosslinking condition. The coatings were characterized by FTIR, XPS, and SEM as well as TGA and DSC analyses. Sustained release of azulene was observed, and there was a correlation between azulene delivery rates and the hydrophobicity of the coating. These results provide a potentially useful platform for the rational design of cotton-based controlled-release systems for bioactive molecule delivery applications.

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References

  1. Nechifor, CD, Dorohoi, DO, Ciobanu, C, “The Influence of Gamma Radiations on Physico-chemical Properties of Some Polymer Membranes.” Rom. Rep. Phys., 54 (3–4) 349–359 (2009)

    CAS  Google Scholar 

  2. Anastas, PT, Kirchhoff, MM, “Origins, Current Status, and Future Challenges of Green Chemistry.” Acc. Chem. Res., 35 (9) 686–694 (2002)

    CAS  Google Scholar 

  3. Tahara, T, Shibata, T, Nakamura, M, Yamashita, H, Yoshioka, D, Okubo, M, Maruyama, N, Kamano, T, Kamiya, Y, Nakagawa, Y, Fujita, H, Nagasaka, M, Iwata, M, Takahama, K, Watanabe, M, Hirata, I, Arisawa, T, “Effect of MDR1 Gene Promoter Methylation in Patients with Ulcerative Colitis.” Int. J. Mol. Med., 23 (4) 521–527 (2009)

    CAS  Google Scholar 

  4. Cerempei, A, Guguianu, E, Muresan, I, Horhogea, C, Rîmbu, C, Borhan, O, “Antimicrobial Controlled Release Systems for the Knitted Cotton Fabrics Based on Natural Substances.” Fibers Polym., 16 (8) 1688–1695 (2015)

    CAS  Google Scholar 

  5. Abdel-Mohsen, AM, Aly, AS, Hrdina, R, Montaser, AS, Hebeish, A, “Biomedical Textiles Through Multifunctioalization of Cotton Fabrics Using Innovative Methoxypolyethylene Glycol-N-Chitosan Graft Copolymer.” J. Polym. Environ., 20 (1) 104–116 (2012)

    CAS  Google Scholar 

  6. Ye, W, Xin, JH, Li, P, Lee, KLD, Kwong, TL, “Durable Antibacterial Finish on Cotton Fabric by Using Chitosan-Based Polymeric Core–Shell Particles.” J. Appl. Polym. Sci., 102 (2) 1787–1793 (2006)

    CAS  Google Scholar 

  7. Wang, X, Du, Y, Fan, L, Liu, H, Hu, Y, “Chitosan–Metal Complexes as Antimicrobial Agent: Synthesis, Characterization and Structure-Activity Study.” Polym. Bull., 55 (1–2) 105–113 (2005)

    CAS  Google Scholar 

  8. Liu, Y, Ma, K, Li, R, Ren, X, Huang, TS, “Antibacterial Cotton Treated with N-Halamine and Quaternary Ammonium Salt.” Cellulose, 20 (6) 3123–3130 (2013)

    CAS  Google Scholar 

  9. Su, CH, Kumar, GV, Adhikary, S, Velusamy, P, Pandian, K, Anbu, P, “Preparation of Cotton Fabric Using Sodium Alginate-Coated Nanoparticles to Protect Against Nosocomial Pathogens.” Biochem. Eng. J., 117 28–35 (2017)

    CAS  Google Scholar 

  10. Rehan, M, Zaghloul, S, Mahmoud, FA, Montaser, AS, Hebeish, A, “Design of Multi-functional Cotton Gauze with Antimicrobial and Drug Delivery Properties.” Mater. Sci. Eng. C, 80 29–37 (2017)

    CAS  Google Scholar 

  11. Lee, HY, Park, HK, Lee, YM, Kim, K, Park, SB, “A Practical Procedure for Producing Silver Nanocoated Fabric and Its Antibacterial Evaluation for Biomedical Applications.” Chem. Commun., 28 2959–2961 (2007)

    Google Scholar 

  12. Abramiuc, D, Ciobanu, L, Muresan, R, Chiosac, M, Muresan, A, “Antibacterial Finishing of Cotton Fabrics Using Biologically Active Natural Compounds.” Fibers Polym., 14 (11) 1826–1833 (2013)

    CAS  Google Scholar 

  13. Cerkez, I, “Rapid Disinfection by N-Halamine Polyelectrolytes.” J. Bioact. Compat. Polym., 28 (1) 86–96 (2013)

    CAS  Google Scholar 

  14. Cerkez, I, Kocer, HB, Worley, SD, Broughton, RM, Huang, TS, “N-Halamine Biocidal Coatings Via a Layer-by-Layer Assembly Technique.” Langmuir, 27 (7) 4091–4097 (2011)

    CAS  Google Scholar 

  15. Zhao, Y, Xu, Z, Wang, X, Lin, T, “Superhydrophobic and UV-Blocking Cotton Fabrics Prepared by Layer-by-Layer Assembly of Organic UV Absorber Intercalated Layered Double Hydroxides.” Appl. Surf. Sci., 286 364–370 (2013)

    CAS  Google Scholar 

  16. Wang, Q, Hauser, PJ, “Developing a Novel UV Protection Process for Cotton Based on Layer-by-Layer Self-Assembly.” Carbohydr. Polym., 81 (2) 491–496 (2010)

    CAS  Google Scholar 

  17. Langer, R, Tirrell, DA, “Designing Materials for Biology and Medicine.” Nature, 428 (6982) 487–492 (2004)

    CAS  Google Scholar 

  18. Granick, S, Kumar, SK, Amis, EJ, Antonietti, M, Balazs, AC, Chakraborty, AK, Grest, GS, Hawker, C, Janmey, P, Kramer, EJ, Nuzzo, R, Russell, TP, Safinya, CR, “Macromolecules at Surfaces: Research Challenges and Opportunities from Tribology to Biology.” J. Polym. Sci. Part B Polym. Phys., 41 (22) 2755–2793 (2003)

    CAS  Google Scholar 

  19. Hu, J, “Controlled Release of Hydrogel Modified Textile Products.” J. Control. Release, 152 e31–e33 (2011)

    CAS  Google Scholar 

  20. Hashemikia, S, Hemmatinejad, N, Ahmadi, E, Montazer, M, “A Novel Cotton Fabric with Anti-bacterial and Drug Delivery Properties Using SBA-15-NH2/Polysiloxane Hybrid Containing Tetracycline.” Mater. Sci. Eng. C, 59 429–437 (2016)

    CAS  Google Scholar 

  21. Wu, Y, Yang, Y, Liu, H, Yao, X, Leng, F, Chen, Y, Tian, W, “Long-Term Antibacterial Protected Cotton Fabric Coating by Controlled Release of Chlorhexidine Gluconate from Halloysite Nanotubes.” RSC Adv., 7 (31) 18917–18925 (2017)

    CAS  Google Scholar 

  22. Lynn, DM, Langer, R, “Degradable Poly(β-amino esters): Synthesis, Characterization, and Self-Assembly with Plasmid DNA.” J. Am. Chem. Soc., 122 (44) 10761–10768 (2000)

    CAS  Google Scholar 

  23. Lakes, AL, Peyyala, R, Ebersole, JL, Puleo, DA, Hilt, JZ, Dziubla, TD, “Synthesis and Characterization of an Antibacterial Hydrogel Containing Covalently Bound Vancomycin.” Biomacromolecules, 15 (8) 3009–3018 (2014)

    CAS  Google Scholar 

  24. Huang, S, Fu, X, “Naturally Derived Materials-Based Cell and Drug Delivery Systems in Skin Regeneration.” J. Control. Release, 142 (2) 149–159 (2010)

    CAS  Google Scholar 

  25. Zhang, Y, Wang, R, Hua, Y, Baumgartner, R, Cheng, J, “Trigger-Responsive Poly(β-amino ester) Hydrogels.” ACS Macro Lett., 3 (7) 693–697 (2014)

    CAS  Google Scholar 

  26. Chen, D, Wu, M, Chen, J, Zhang, C, Pan, T, Zhang, B, Tian, H, Chen, X, Sun, J, “Robust, Flexible, and Bioadhesive Free-Standing Films for the Co-delivery of Antibiotics and Growth Factors.” Langmuir, 30 (46) 13898–13906 (2014)

    CAS  Google Scholar 

  27. Wood, KC, Boedicker, JQ, Lynn, DM, Hammond, PT, “Tunable Drug Release from Hydrolytically Degradable Layer-by-Layer thin Films.” Langmuir, 21 (4) 1603–1609 (2005)

    CAS  Google Scholar 

  28. Feng, L, Wang, Y, Luo, Z, Huang, Z, Zhang, Y, Guo, K, Ye, D, “Dual Stimuli-Responsive Nanoparticles for Controlled Release of Anticancer and Anti-inflammatory Drugs Combination.” Chem. A Eur. J., 23 (39) 9397–9406 (2017)

    CAS  Google Scholar 

  29. Hofmann, D, Entrialgo-Castaño, M, Kratz, K, Lendlein, A, “Knowledge-Based Approach Towards Hydrolytic Degradation of Polymer-Based Biomaterials.” Adv. Mater., 21 (32–33) 3237–3245 (2009)

    CAS  Google Scholar 

  30. Das, D, Das, R, Ghosh, P, Dhara, S, Panda, AB, Pal, S, “Dextrin Cross Linked with Poly(HEMA): A Novel Hydrogel for Colon Specific Delivery of Ornidazole.” RSC Adv., 3 (47) 25340–25350 (2013)

    CAS  Google Scholar 

  31. Mi, FL, Wu, YB, Shyu, SS, Schoung, JY, Huang, YB, Tsai, YH, Hao, JY, “Control of Wound Infections Using a Bilayer Chitosan Wound Dressing with Sustainable Antibiotic Delivery.” J. Biomed. Mater. Res., 59 (3) 438–449 (2002)

    CAS  Google Scholar 

  32. Gomes, AP, Mano, JF, Queiroz, JA, Gouveia, IC, “Incorporation of Antimicrobial Peptides on Functionalized Cotton Gauzes for Medical Applications.” Carbohydr. Polym., 127 451–461 (2015)

    CAS  Google Scholar 

  33. Pollini, M, Paladini, F, Sannino, A, Maffezzoli, A, “Development of Hybrid Cotton/Hydrogel Yarns with Improved Absorption Properties for Biomedical Applications.” Mater. Sci. Eng. C, 63 563–569 (2016)

    CAS  Google Scholar 

  34. Chen, X, Prow, TW, Crichton, ML, Jenkins, DW, Roberts, MS, Frazer, IH, Fernando, GJ, Kendall, MA, “Dry-Coated Microprojection Array Patches for Targeted Delivery of Immunotherapeutics to the Skin.” J. Control. Release, 139 (3) 212–220 (2009)

    CAS  Google Scholar 

  35. Matsumura, S, Hlil, AR, Lepiller, C, Gaudet, J, Guay, D, Shi, Z, Holdcroft, S, Hay, AS, “Ionomers for Proton Exchange Membrane Fuel Cells with Sulfonic Acid Groups on the End-Groups: Novel Branched Poly(Ether-Ketone)s.” Am. Chem. Soc. Polym. Prepr. Div. Polym. Chem., 49 (1) 511–512 (2008)

    CAS  Google Scholar 

  36. Hagberg, EC, Malkoch, M, Ling, Y, Hawker, CJ, Carter, KR, “Effects of Modulus and Surface Chemistry of Thiol-Ene Photopolymers in Nanoimprinting.” Nano Lett., 7 (2) 233–237 (2007)

    CAS  Google Scholar 

  37. Melnick, JL, “Advantages and Disadvantages of Killed and Live Poliomyelitis Vaccines.” Bull. World Health Organ., 56 (1) 21–38 (1978)

    CAS  Google Scholar 

  38. Shoji, T, Ito, S, “Azulene-Based Donor-Acceptor Systems: Synthesis, Optical, and Electrochemical Properties.” Chem. A Eur. J., 23 (66) 16696–16709 (2017)

    CAS  Google Scholar 

  39. Murai, M, Iba, S, Ota, H, Takai, K, “Azulene-Fused Linear Polycyclic Aromatic Hydrocarbons with Small Bandgap, High Stability, and Reversible Stimuli Responsiveness.” Org. Lett., 19 (20) 5585–5588 (2017)

    CAS  Google Scholar 

  40. Bui, QN, Li, Y, Jang, MS, Huynh, DP, Lee, JH, Lee, DS, “Redox- and pH-Sensitive Polymeric Micelles Based on Poly(β-amino ester)-Grafted Disulfide Methylene Oxide Poly(ethylene glycol) for Anticancer Drug Delivery.” Macromolecules, 48 (12) 4046–4054 (2015)

    CAS  Google Scholar 

  41. Amir, E, Amir, RJ, Campos, LM, Hawker, CJ, “Stimuli-Responsive Azulene-Based Conjugated Oligomers with Polyaniline-Like Properties.” J. Am. Chem. Soc., 133 (26) 10046–10049 (2011)

    CAS  Google Scholar 

  42. Amir, E, Murai, M, Amir, RJ, Cowart, JS, Jr, Chabinyc, ML, Hawker, CJ, “Conjugated Oligomers Incorporating Azulene Building Blocks: Seven- vs. Five-Membered Ring Connectivity.” Chem. Sci., 5 (11) 4483–4489 (2014)

    CAS  Google Scholar 

  43. Uchida, R, Sato, T, Tanigawa, H, Uno, K, “Azulene Incorporation and Release by Hydrogel Containing Methacrylamide Propyltrimenthylammonium Chloride, and Its Application to Soft Contact Lens.” J. Control. Release, 92 (3) 259–264 (2003)

    CAS  Google Scholar 

  44. Peet, J, Selyutina, A, Bredihhin, A, “Antiretroviral (HIV-1) Activity of Azulene Derivatives.” Bioorg. Med. Chem., 24 (8) 1653–1657 (2016)

    CAS  Google Scholar 

  45. Chen, D, Yu, S, Van Ofwegen, L, Proksch, P, Lin, W, “Anthogorgienes A-O, New Guaiazulene-Derived Terpenoids from a Chinese Gorgonian Anthogorgia Species, and Their Antifouling and Antibiotic Activities.” J. Agric. Food Chem., 60 (1) 112–123 (2012)

    CAS  Google Scholar 

  46. Nakamura, H, Sekido, M, Yamamoto, Y, “Synthesis of Carboranes Containing an Azulene Framework and In Vitro Evaluation as Boron Carriers.” J. Med. Chem., 40 (18) 2825–2830 (1997)

    CAS  Google Scholar 

  47. Gosavi, PM, Moroz, YS, Korendovych, IV, “β-(1-Azulenyl)-l-alanine: A Functional Probe for Determination of pKa of Histidine Residues.” Chem. Commun., 51 (25) 5347–5350 (2015)

    CAS  Google Scholar 

  48. Pham, W, Weissleder, R, Tung, CH, “An Azulene Dimer as a Near-Infrared Quencher.” Angew. Chem. Int. Ed., 41 (19) 3659–3662 (2002)

    CAS  Google Scholar 

  49. Yamane, C, Aoyagi, T, Ago, M, Sato, K, Okajima, K, Takahashi, T, “Two Different Surface Properties of Regenerated Cellulose due to Structural Anisotropy.” Polym. J., 38 (8) 819–826 (2006)

    CAS  Google Scholar 

  50. Pascault, JP, Williams, RJJ, “Overview of Thermosets: Structure, Properties and Processing for Advanced Applications.” In: Guo, Q (ed.) Thermosets. Structure, Properties and Applications, pp. 3–27 (2012)

  51. Kelnar, I, Kratochvíl, J, Kaprálková, L, Zhigunov, A, Padovec, Z, Růžička, M, Nevoralová, M, “Antagonistic Effects on Mechanical Properties of Microfibrillar Composites with Dual Reinforcement: Explanation by FEA Model of Soft Interface.” J. Appl. Polym. Sci., 134 (20) 1–9 (2017)

    Google Scholar 

  52. Zhang, J, Fredin, NJ, Janz, JF, Sun, B, Lynn, DM, “Structure/Property Relationships in Erodible Multilayered Films: Influence of Polycation Structure on Erosion Profiles and the Release Of Anionic Polyelectrolytes.” Langmuir, 22 (1) 239–245 (2006)

    Google Scholar 

  53. Tang, S, Yin, Q, Zhang, Z, Gu, W, Chen, L, Yu, H, Huang, Y, Chen, X, Xu, M, Li, Y, “Co-delivery of Doxorubicin and RNA Using pH-Sensitive Poly(β-amino ester) Nanoparticles for Reversal of Multidrug Resistance of Breast Cancer.” Biomaterials, 35 (23) 6047–6059 (2014)

    CAS  Google Scholar 

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This work was sponsored by the Israeli Ministry of Economy Innovation Authority Grant #57727.

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Correspondence to Elizabeth Amir.

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Hartman, C., Popowski, Y., Raichman, D. et al. Biodegradable polymer coating for controlled release of hydrophobic functional molecules from cotton fabrics. J Coat Technol Res 17, 669–679 (2020). https://doi.org/10.1007/s11998-019-00278-3

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