Global to push GA events into
skip to main content

Title: Acid-degradable and bioerodible modified polyhydroxylated materials

Compositions and methods of making a modified polyhydroxylated polymer comprising a polyhydroxylated polymer having reversibly modified hydroxyl groups, whereby the hydroxyl groups are modified by an acid-catalyzed reaction between a polydroxylated polymer and a reagent such as acetals, aldehydes, vinyl ethers and ketones such that the modified polyhydroxylated polymers become insoluble in water but freely soluble in common organic solvents allowing for the facile preparation of acid-sensitive materials. Materials made from these polymers can be made to degrade in a pH-dependent manner. Both hydrophobic and hydrophilic cargoes were successfully loaded into particles made from the present polymers using single and double emulsion techniques, respectively. Due to its ease of preparation, processability, pH-sensitivity, and biocompatibility, of the present modified polyhydroxylated polymers should find use in numerous drug delivery applications.
Inventors:
; ; ;
Issue Date:
OSTI Identifier:
1356292
Assignee:
The Regents of the University of California LBNL
Patent Number(s):
9,644,039
Application Number:
12/987,679
Contract Number:
AC02-05CH11231
Resource Relation:
Patent File Date: 2011 Jan 10
Research Org:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org:
USDOE
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 59 BASIC BIOLOGICAL SCIENCES

Other works cited in this record:

Polymers and polymer-peptide conjugates
patent, March 1993

Nanogel networks and biological agent compositions thereof
patent, December 2001

Microgel particles for the delivery of bioactive materials
patent, June 2006

2'-Fluoronucleosides
patent, December 2007

Microgel particles for the delivery of bioactive materials
patent, March 2010

Main chain acid-degradable polymers for the delivery of bioactive materials
patent, March 2012

Candida albicans mannan–protein conjugate as vaccine candidate
journal, February 2003

In Vitro Evaluation of Microparticles and Polymer Gels for Use as Nasal Platforms for Protein Delivery
journal, March 1999
  • Witschi, Claudia; Mrsny, Randall J.
  • Pharmaceutical Research, Vol. 16, Issue 3, p. 382-390
  • DOI: 10.1023/A:1018869601502

Acetals as pH-Sensitive Linkages for Drug Delivery
journal, November 2004
  • Gillies, Elizabeth R.; Goodwin, Andrew P.; Fréchet, Jean M. J.
  • Bioconjugate Chemistry, Vol. 15, Issue 6, p. 1254-1263
  • DOI: 10.1021/bc049853x

Acetalated dextran is a chemically and biologically tunable material for particulate immunotherapy
journal, March 2009
  • Broaders, K. E.; Cohen, J. A.; Beaudette, T. T.
  • Proceedings of the National Academy of Sciences, Vol. 106, Issue 14, p. 5497-5502
  • DOI: 10.1073/pnas.0901592106

Acetal-Derivatized Dextran: An Acid-Responsive Biodegradable Material for Therapeutic Applications
journal, August 2008
  • Bachelder, Eric M.; Beaudette, Tristan T.; Broaders, Kyle E.
  • Journal of the American Chemical Society, Vol. 130, Issue 32, p. 10494-10495
  • DOI: 10.1021/ja803947s

Fully Acid-Degradable Biocompatible Polyacetal Microparticles for Drug Delivery
journal, April 2008
  • Paramonov, Sergey E.; Bachelder, Eric M.; Beaudette, Tristan T.
  • Bioconjugate Chemistry, Vol. 19, Issue 4, p. 911-919
  • DOI: 10.1021/bc7004472

Conjugation of yeast mannans with protein employing cyanopyridinium agent (CDAP) – an effective route of antifungal vaccine preparation
journal, January 2000
  • Bystrický, Slavomír; Machova´, Eva; Bartek, Peter
  • Glycoconjugate Journal, Vol. 17, Issue 10, p. 677-680
  • DOI: 10.1023/A:1011002118819

Degradation and Release Behavior of Dextran-Based Hydrogels
journal, August 1997
  • van Dijk-Wolthuis, W. N. E.; Hoogeboom, J. A. M.; van Steenbergen, M. J.
  • Macromolecules, Vol. 30, Issue 16, p. 4639-4645
  • DOI: 10.1021/ma9704018

Similar records in DOepatents and OSTI.GOV collections: