Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Original Article
  • Published:

One-pot amphiphilic engineering of bioresorbable polymers for constructing colloidal vesicles and prolonging protein delivery

Abstract

In this study, we sought to develop methods for amphiphilic engineering of bioresorbable polymers, sorbitan–poly(lactic acid) (sorbitan–PLA) and poly(ethylene glycol)–polylactic acid (PEG–PLA), by melt polycondensation of lactic acid in the presence of the binary initiators sorbitan and methoxy PEG in a single reactor. Briefly, oligo(lactic acid) (OLA) was first prepared by distilling water out of lactic acid under vacuum; then, sorbitan and methoxy PEG were introduced in the reactor, followed by the simultaneous polycondensation of OLA onto sorbitan and methoxy PEG, resulting in a mixture containing sorbitan–PLA/PEG–PLA copolymers. Without further purification, the recovered products were dissolved in saline buffer, mixed with squalane oil, and then homogenized to construct a stable colloidal vesicle. Then, we conducted a mechanistic study to progressively elucidate the relationship between the dispersion structure and the sustained release of a model protein bovine serum albumin. This one-pot approach has potential for applications and commercial use in the field of biodegradable controlled-release delivery systems.

This is a preview of subscription content, access via your institution

Access options

Buy this article

Prices may be subject to local taxes which are calculated during checkout

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Kalasz H, Antal I. Drug excipients. Curr Med Chem 2006;13:2535–63.

    Article  CAS  Google Scholar 

  2. Wakelin SH, Cooper S, Marren P, Shaw S. Sorbitan mono-oleate: a potential allergen in paste bandages. Contact Dermat 1996;35:377.

    Article  CAS  Google Scholar 

  3. Sun H, Yang R, Wang J, Yang X, Tu J, Xie L, Li C, Lao Q, Sun C. Component-based biocompatibility and safety evaluation of polysorbate 80. RSC Adv 2017;7:15127–38.

    Article  CAS  Google Scholar 

  4. Huang CY, Huang CH, Liu SJ, Chen HW, Leng CH, Chong P, Huang MH. Polysorbasome: a colloidal vesicle contoured by polymeric bioresorbable amphiphiles as an immunogenic depot for vaccine delivery. ACS Appl Mater Interfaces 2018;10:12553–61.

    Article  CAS  Google Scholar 

  5. Ishikawa H, Suzuki T, Hayashi Y. High-yielding synthesis of the anti-influenza neuramidase inhibitor (-)-oseltamivir by three “one-pot” preparations. Angew Chem Int Ed. 2009;48:1304–7.

    Article  CAS  Google Scholar 

  6. Li S, Anjard S, Rashkov I, Vert M. Hydrolytic degradation of PLA/PEO/PLA triblock copolymers prepared in the presence of Zn metal or CaH2. Polymer 1998;39:5421–30.

    Article  CAS  Google Scholar 

  7. Rashkov I, Manolova N, Li SM, Espartero JL, Vert M. Synthesis, characterization, and hydrolytic degradation of PLA/PEO/PLA triblock copolymers with short poly(l-lactic acid) chains. Macromolecules 1996;29:50–6.

    Article  CAS  Google Scholar 

  8. Wu H, Zhu H, Zhuang J, Yang S, Liu C, Cao YC. Water-soluble nanocrystals through dual-interaction ligands. Angew Chem Int Ed 2008;47:3730–4.

    Article  CAS  Google Scholar 

  9. Maharana T, Mohanty B, Negi YS. Melt–solid polycondensation of lactic acid and its biodegradability. Prog Polym Sci 2009;34:99–124.

    Article  CAS  Google Scholar 

  10. Shum HC, Zhao YJ, Kim SH, Weitz DA. Multicompartment polymersomes from double emulsions. Angew Chem Int Ed 2011;50:1648–51.

    Article  CAS  Google Scholar 

  11. Huang MH, Chou AH, Lien SP, Chen HW, Huang CY, Chen WW, Chong P, Liu SJ, Leng CH. Formulation and immunological evaluation of novel vaccine delivery systems based on bioresorbable poly(ethylene glycol)-block-poly(lactide-co-ε-caprolactone). J Biomed Mater Res Part B 2009;90B:832–41.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Health Research Institutes of Taiwan (grant number 108A1-IVPP19-014) and by a grant from the Ministry of Science and Technology of Taiwan (grant number MOST 106-2314-B-400-016-MY3).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ming-Hsi Huang.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Additional information

Publisher’s note Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Huang, CY., Cheng, YJ., Ho, HM. et al. One-pot amphiphilic engineering of bioresorbable polymers for constructing colloidal vesicles and prolonging protein delivery. Polym J 52, 237–244 (2020). https://doi.org/10.1038/s41428-019-0267-3

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41428-019-0267-3

Search

Quick links