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Modifying Polydiacetylene Vesicle Compositions to Reduce Non-Specific Interactions

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Abstract

Polydiacetylene (PDA) vesicles provide useful stimuli-responsive behavior as well as by the modular structure afford a means for the design of sensing and delivery systems with tunable target specificity. To reduce inherent non-specific interaction with either anionic or cationic formulations of polydiacetylene vesicles, we explored the use of various lengths of poly(ethylene glycol) (PEG) amphiphiles for integration and polymerization within PDA vesicles. Our results established that as little as 1% of polyethylene glycol amphiphile integration into anionic vesicles was sufficient to significantly reduce non-specific association with mammalian cells. Similarly integrating a low percent of PEG amphiphile content within cationic vesicles could also significantly reduce non-specific cell association, and moreover reduced cytotoxicity. These results may be prove useful in augmenting PDA vesicles formulations for reduced non-specific interaction which is of particularly interest to enhancing selectivity in vesicles designed with integrated targeting moieties for sensing and drug delivery applications.

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References

  1. R. Jelinek, S. Okada, S. Norvez, and D. Charych, Chem. Biology, 5, 619 (1998).

    Article  CAS  Google Scholar 

  2. Y.-L. Su, J.-R. Li, and L. Jiang, Colloids Surf. B: Biointerfaces, 38, 29 (2004).

    Article  CAS  PubMed  Google Scholar 

  3. F. Fang, F. Meng, and L. Luo, Mater. Chem. Frontiers, 4, 1089 (2020).

    Article  CAS  Google Scholar 

  4. D. J. Ahn, E.-H. Chae, G. S. Lee, H.-Y. Shim, T.-E. Chang, K.-D. Ahn, and J.-M. Kim, J. Am. Chem. Soc., 125, 8976 (2003).

    Article  CAS  PubMed  Google Scholar 

  5. K. W. Kim, J. M. Lee, Y. M. Kwon, T.-Y. Choi, J. Y. H. Kim, S. Bae, and J.-A. Song, Macromol. Res., 26, 284 (2018).

    Article  CAS  Google Scholar 

  6. Q. Cheng and R. C. Stevens, Langmuir, 14, 1974 (1998).

    Article  CAS  Google Scholar 

  7. C. Cui, H. Choi, G. S. Lee, and D. J. Ahn, J. Nanosci. Nanotechnol., 11, 5754 (2011).

    Article  CAS  PubMed  Google Scholar 

  8. S. Okada, S. Peng, W. Spevak, and D. Charych, Acc. Chem. Res., 31, 229 (1998).

    Article  CAS  Google Scholar 

  9. F. Jannah, J.-H. Kim, J.-W. Lee, J.-M. Kim, J.-M. Kim, and H. Lee, Front. Mater., 5, 57 (2018).

    Article  Google Scholar 

  10. D. Yun, D. Jeong, E. Cho, and S. Jung, Plos One, 10, e0143454 (2015).

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  11. S. Zhang, B. Shi, and G. Yang, Macromol. Res., 28, 51 (2020).

    Article  CAS  Google Scholar 

  12. G. Yang, Z. Nie, S. Zhang, Z. Ge, J. Zhao, J. Zhang, and B. Li, Macromol. Res., 28, 1192 (2020).

    Article  CAS  Google Scholar 

  13. M. J. Shin, Macromol. Res., 28, 703 (2020).

    Article  CAS  Google Scholar 

  14. C. Guo, S. Liu, Z. Dai, C. Jiang, and W. Li, Colloids Surf. B: Biointerfaces, 76, 362 (2010).

    Article  CAS  PubMed  Google Scholar 

  15. J. Jaworski, K. Yokoyama, C. Zueger, W.-J. Chung, S.-W. Lee, and A. Majumdar, Langmuir, 27, 3180 (2011).

    Article  CAS  PubMed  Google Scholar 

  16. B. Yoon, J. Jaworski, and J.-M. Kim, Supramol. Chem., 25, 54 (2013).

    Article  CAS  Google Scholar 

  17. S. Guo, L. Lv, Y. Shen, Z. Hu, Q. He, and X. Chen, Sci. Rep., 6, 21459 (2016).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. C. Guo, L. Zeng, S. Liu, Q. Chen, Z. Dai, and X. Wu, J. Nanosci. Nanotechnol., 12, 245 (2012).

    Article  CAS  PubMed  Google Scholar 

  19. O. Yarimaga, J. Jaworski, B. Yoon, and J.-M. Kim, Chem. Commun., 48, 2469 (2012).

    Article  CAS  Google Scholar 

  20. J. Lee, B. Yoon, D. Y. Ham, O. Yarimaga, C. W. Lee, J. Jaworski, and J. M. Kim, Macromol. Chem. Phys., 213, 893 (2012).

    Article  CAS  Google Scholar 

  21. O. Yarimaga, M. Im, Y.-K. Choi, T. W. Kim, Y. K. Jung, H. G. Park, S. Lee, and J.-M. Kim, Macromol. Res., 18, 404 (2010).

    Article  CAS  Google Scholar 

  22. D.-H. Park, B. J. Park, and J.-M. Kim, Macromol. Res., 24, 943 (2016).

    Article  CAS  Google Scholar 

  23. A. D. White, A. K. Nowinski, W. Huang, A. J. Keefe, F. Sun, and S. Jiang, Chem. Sci., 3, 3488 (2012).

    Article  CAS  Google Scholar 

  24. P. Bongrand, J. Disper. Sci. Technol., 19, 963 (1998).

    Article  Google Scholar 

  25. A. David Nelson, P. Shiveshwarkar, B. Lim, G. Rojas, I. Abure, A. Shrestha, and J. Jaworski, Biosensors, 10, 132 (2020).

    Article  PubMed Central  CAS  Google Scholar 

  26. J. E. Contreras-Naranjo and O. Aguilar, Biosensors, 9, 15 (2019).

    Article  CAS  PubMed Central  Google Scholar 

  27. T. Waterboer, P. Sehr, and M. Pawlita, J. Immunol. Meth., 309, 200 (2006).

    Article  CAS  Google Scholar 

  28. Y. Zhang, J. Northcutt, T. Hanks, I. Miller, B. Pennington, R. Jelinek, I. Han, and P. Dawson, Food Chem., 221, 515 (2017).

    Article  CAS  PubMed  Google Scholar 

  29. C. S. Schneider, A. G. Bhargav, J. G. Perez, A. S. Wadajkar, J. A. Winkles, G. F. Woodworth, and A. J. Kim, J. Control. Release, 219, 331 (2015).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. J. G. Dancy, A. S. Wadajkar, C. S. Schneider, J. R. Mauban, O. G. Goloubeva, G. F. Woodworth, J. A. Winkles, and A. J. Kim, J. Control. Release, 238, 139 (2016).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  31. H. Chen, L. Wang, J. Yeh, X. Wu, Z. Cao, Y. A. Wang, M. Zhang, L. Yang, and H. Mao, Biomaterials, 31, 5397 (2010).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  32. J. M. Harris, in Poly(ethylene glycol) Chemistry, Springer, 1992, pp 1–14.

  33. D. E. Discher, V. Ortiz, G. Srinivas, M. L. Klein, Y. Kim, D. Christian, S. Cai, P. Photos, and F. Ahmed, Prog. Polym. Sci., 32, 838 (2007).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. M. Dzieciuch, S. Rissanen, N. Szydłowska, A. Bunker, M. Kumorek, D. Jamroz, I. Vattulainen, M. Nowakowska, T. Rog, and M. Kepczynski, J. Phys. Chem. B, 119, 6646 (2015).

    Article  CAS  PubMed  Google Scholar 

  35. A. L. Klibanov, K. Maruyama, V. P. Torchilin, and L. Huang, FEBS Lett., 268, 235 (1990).

    Article  CAS  PubMed  Google Scholar 

  36. G. Blume and G. Cevc, Biochim. Biophys. Acta (BBA)-Biomembranes, 1029, 91 (1990).

    Article  CAS  Google Scholar 

  37. K. Knop, R. Hoogenboom, D. Fischer, and U. S. Schubert, Angew. Chem. Int. Ed., 49, 6288 (2010).

    Article  CAS  Google Scholar 

  38. S. Sheth and D. Leckband, Proc. Nat. Acad. Sci., 94, 8399 (1997).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  39. J. Israelachvili, Proc. Nat. Acad. Sci., 94, 8378 (1997).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  40. M. C. Smith, R. M. Crist, J. D. Clogston, and S. E. McNeil, Anal. Bioanal. Chem., 409, 5779 (2017).

    Article  CAS  PubMed  Google Scholar 

  41. A. Bunker, Phys. Procedia, 34, 24 (2012).

    Article  Google Scholar 

  42. N. Mackiewicz, E. Gravel, A. Garofalakis, J. Ogier, J. John, D. M. Dupont, K. Gombert, B. Tavitian, E. Doris, and F. Ducongé, Small, 7, 2786 (2011).

    Article  CAS  PubMed  Google Scholar 

  43. E. Gravel, J. Ogier, T. Arnauld, N. Mackiewicz, F. Ducongé, and E. Doris, Chem. A Eur. J., 18, 400 (2012).

    Article  CAS  Google Scholar 

  44. H. Choi, Y. M. Bae, G. S. Yu, K. M. Huh, and J. S. Choi, J. Nanosci. Nanotechnol., 8, 5104 (2008).

    Article  CAS  PubMed  Google Scholar 

  45. J. Lin and A. Alexander-Katz, ACS Nano, 7, 10799 (2013).

    Article  CAS  PubMed  Google Scholar 

  46. S. De Oliveira and C. Saldanha, Clin. Hemorheol. Microcirc., 44, 63 (2010).

    Article  CAS  PubMed  Google Scholar 

  47. S. Abbina, E. M. Siren, H. Moon, and J. N. Kizhakkedathu, ACS Biomater. Sci. Eng., 4, 3658 (2017).

    Article  PubMed  CAS  Google Scholar 

  48. M. S. de Almeida, E. Susnik, B. Drasler, P. Taladriz-Blanco, A. Petri-Fink, and B. Rothen-Rutishauser, Chem. Soc. Rev., 50, 5397 (2021).

    Article  Google Scholar 

  49. M. Weiss, J. Fan, M. Claudel, T. Sonntag, P. Didier, C. Ronzani, L. Lebeau, and F. Pons, J. Nanobiotechnol., 19, 1 (2021).

    Article  CAS  Google Scholar 

  50. X. Zhou and L. Huang, Biochim. Biophys. Acta (BBA)-Biomembranes, 1189, 195 (1994).

    Article  CAS  Google Scholar 

  51. S. Hama, S. Itakura, M. Nakai, K. Nakayama, S. Morimoto, S. Suzuki, and K. Kogure, J. Control. Release, 206, 67 (2015).

    Article  CAS  PubMed  Google Scholar 

  52. S. Mishra, P. Webster, and M. E. Davis, Europ. J. Cell Biol., 83, 97 (2004).

    Article  CAS  PubMed  Google Scholar 

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Correspondence to Justyn Jaworski.

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Supporting information

Experimental procedure and schematic overviews for the synthesis of PCDA-EDEA, bis-PCDA-PEG (3400 and 8000), absorption spectrum of characteristic blue-phase polydiacetylene vesicles, MTT assay results as well as procedures for FACS, cell culture and MTT assay experiments. The materials are available via the Internet at http://www.springer.com/13233.

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Acknowledgment: This work was supported by the NIGMS of the NIH under Grant Number R15GM135892. The content is the responsibility of the authors and does not represent the official views of the NIH.

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Rojas, G., Shiveshwarkar, P., Lim, B. et al. Modifying Polydiacetylene Vesicle Compositions to Reduce Non-Specific Interactions. Macromol. Res. 29, 449–452 (2021). https://doi.org/10.1007/s13233-021-9059-7

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  • DOI: https://doi.org/10.1007/s13233-021-9059-7

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