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Maleimide-Functionalized Poly(2-Oxazoline)s and Their Conjugation to Elastin-Like Polypeptides.

Publication ,  Journal Article
Nawroth, JF; McDaniel, JR; Chilkoti, A; Jordan, R; Luxenhofer, R
Published in: Macromolecular bioscience
March 2016

The design of drug delivery systems capable of efficiently delivering poorly soluble drugs to target sites still remains a major challenge. Such materials require several different functionalities; typically, these materials should be biodegradable and nontoxic, nonimmunogenic, responsive to their environment, and soluble in aqueous solution while retaining the ability to solubilize hydrophobic drugs. Here, a polypeptide-polymer hybrid of elastin-like polypeptides (ELPs) and poly(2-oxazoline)s (POx) is reported. This paper describes the chemical synthesis, physical characteristics, and drug loading potential of these novel hybrid macromolecules. A novel method is introduced for terminal functionalization of POx with protected maleimide moieties. Following recovery of the maleimide group via a retro Diels-Alder reaction, the consecutive Michael addition of thiol-functionalized ELPs yields the desired protein-polymer conjugate. These conjugates form nanoparticles in aqueous solution capable of solubilizing the anti-cancer drug paclitaxel with up to 8 wt% loading.

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Published In

Macromolecular bioscience

DOI

EISSN

1616-5195

ISSN

1616-5187

Publication Date

March 2016

Volume

16

Issue

3

Start / End Page

322 / 333

Related Subject Headings

  • Recombinant Proteins
  • Polymers
  • Oxazoles
  • Maleimides
  • Elastin
  • 4003 Biomedical engineering
  • 3403 Macromolecular and materials chemistry
  • 0904 Chemical Engineering
  • 0903 Biomedical Engineering
  • 0303 Macromolecular and Materials Chemistry
 

Citation

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Nawroth, J. F., McDaniel, J. R., Chilkoti, A., Jordan, R., & Luxenhofer, R. (2016). Maleimide-Functionalized Poly(2-Oxazoline)s and Their Conjugation to Elastin-Like Polypeptides. Macromolecular Bioscience, 16(3), 322–333. https://doi.org/10.1002/mabi.201500376
Nawroth, Jonas F., Jonathan R. McDaniel, Ashutosh Chilkoti, Rainer Jordan, and Robert Luxenhofer. “Maleimide-Functionalized Poly(2-Oxazoline)s and Their Conjugation to Elastin-Like Polypeptides.Macromolecular Bioscience 16, no. 3 (March 2016): 322–33. https://doi.org/10.1002/mabi.201500376.
Nawroth JF, McDaniel JR, Chilkoti A, Jordan R, Luxenhofer R. Maleimide-Functionalized Poly(2-Oxazoline)s and Their Conjugation to Elastin-Like Polypeptides. Macromolecular bioscience. 2016 Mar;16(3):322–33.
Nawroth, Jonas F., et al. “Maleimide-Functionalized Poly(2-Oxazoline)s and Their Conjugation to Elastin-Like Polypeptides.Macromolecular Bioscience, vol. 16, no. 3, Mar. 2016, pp. 322–33. Epmc, doi:10.1002/mabi.201500376.
Nawroth JF, McDaniel JR, Chilkoti A, Jordan R, Luxenhofer R. Maleimide-Functionalized Poly(2-Oxazoline)s and Their Conjugation to Elastin-Like Polypeptides. Macromolecular bioscience. 2016 Mar;16(3):322–333.
Journal cover image

Published In

Macromolecular bioscience

DOI

EISSN

1616-5195

ISSN

1616-5187

Publication Date

March 2016

Volume

16

Issue

3

Start / End Page

322 / 333

Related Subject Headings

  • Recombinant Proteins
  • Polymers
  • Oxazoles
  • Maleimides
  • Elastin
  • 4003 Biomedical engineering
  • 3403 Macromolecular and materials chemistry
  • 0904 Chemical Engineering
  • 0903 Biomedical Engineering
  • 0303 Macromolecular and Materials Chemistry