Nonlinear fatty acid terminated polyanhydrides

D. Teomim, A. J. Domb

Research output: Contribution to journalArticlepeer-review

49 Scopus citations

Abstract

A systemic study on the synthesis, characterization, degradation, drug release, and stability of nonlinear fatty acid terminated poly(sebacic anhydride) (PSA) is reported. Ricinoleic acid was transformed into a nonlinear fatty acid by esterification with fatty acid chlorides of C8-C18 chain length in the presence of pyridine. Pure nonlinear fatty acids were obtained by purification of the reaction product using column chromatography. Poly(sebacic acid)s terminated with 30 wt % of various nonlinear fatty acids were synthesized by melt condensation to yield waxy off-white materials with molecular weights in the range of 5000-9000. The terminated polymers are soluble in common organic solvents and melt at temperatures between 70 and 79 °C, which allow their fabrication into microspheres and implants. These polymers degrade into their counterparts during a period of a few weeks while constantly releasing an incorporated drug. The incorporation of nonlinear fatty acid terminals to poly(sebacic anhydride) increased the polymer hydrophobicity and decreased polymer crystallinity when compared to PSA or to linear fatty acid terminated PSA. The hydrophobic nonlinear side chains retard water from penetrating into the polymer mass, which resulted in higher stability and surface erosion front mechanism of polymer degradation and drug release.

Original languageEnglish
Pages (from-to)37-44
Number of pages8
JournalBiomacromolecules
Volume2
Issue number1
DOIs
StatePublished - 2001
Externally publishedYes

Funding

FundersFunder number
National Cancer InstituteU01CA052857

    Fingerprint

    Dive into the research topics of 'Nonlinear fatty acid terminated polyanhydrides'. Together they form a unique fingerprint.

    Cite this