Jump to main content
Jump to site search

Issue 4, 2014
Previous Article Next Article

Scalable synthesis and derivation of functional polyesters bearing ene and epoxide side chains

Author affiliations

Abstract

Functional polyester chemistry is well suited to improve delivery of biomacromolecular drugs because it enables tuning of degradation profiles and inclusion of key functional groups (e.g. cationic charges for nucleic acid binding). However, current approaches to introduce functionality suffer from inadequate scalability and modularity. We have developed a scalable library of functional polyesters based on the polymerization of trimethylolpropane allyl ether (TPAE) with diacid chlorides (poly(TPAE-co-AC)s). The reactive side chains can be easily modified with various functional thiols (e.g. alkyl-, amino-, and PEG-) and amines to generate a diverse set of materials, thereby tuning the chemistry for potential opportunities in drug delivery. The polymerization occurs readily under mild conditions at room temperature with Mw for poly(TPAE-co-suberoyl chloride) exceeding 42 000 g mol−1. In addition, poly(TPAE-co-adipoyl chloride) was polymerized on a 100+ gram scale in 71% final isolated yield. Due to the structural similarity to established non-functional polyesters such as PLGA, these new materials may find broad application as functional polyesters for gene delivery, tissue engineering, and other nanotechnology applications.

Graphical abstract: Scalable synthesis and derivation of functional polyesters bearing ene and epoxide side chains

Back to tab navigation

Supplementary files

Publication details

The article was received on 22 Oct 2013, accepted on 13 Nov 2013 and first published on 13 Nov 2013


Article type: Paper
DOI: 10.1039/C3PY01474F
Citation: Polym. Chem., 2014,5, 1362-1371
  •   Request permissions

    Scalable synthesis and derivation of functional polyesters bearing ene and epoxide side chains

    Y. Yan and D. J. Siegwart, Polym. Chem., 2014, 5, 1362
    DOI: 10.1039/C3PY01474F

Search articles by author

Spotlight

Advertisements