Journal article
Long-term release of a thiobenzamide from a backbone functionalized poly(lactic acid)
Polymer chemistry, Vol.6(40), pp.7188-7195
10/01/2015
DOI: 10.1039/c5py01059d
PMCID: PMC4746005
PMID: 26870159
Abstract
Hydrogen sulfide is emerging as a critically important molecule in medicine, yet there are few methods for the long-term delivery of molecules that degrade to release H sub(2)S. In this paper the first long-term release of a thiobenzamide that degrades to release H sub(2)S is described. A series of polymers were synthesized by the copolymerization of l-lactide and a lactide functionalized with 4-hydroxythiobenzamide. A new method to attach functional groups to a derivative of l-lactide is described based on the addition of a thiol to an alpha , beta -unsaturated lactide using catalytic I sub(2). This reaction proceeded under mild conditions and did not ring-open the lactone. The copolymers had molecular weights from 8 to 88 kg mol super(-1) with PDIs below 1.50. Two sets of microparticles were fabricated from a copolymer; the average diameters of the microparticles were 0.53 and 12 mu m. The degradation of the smaller microparticles was investigated in buffered water to demonstrate the slow release of thiobenzamide over 4 weeks. Based on the ability to synthesize polymers with different loadings of thiobenzamide and that thiobenzamide is a known precursor to H sub(2)S, these particles provide a polymer-based method to deliver H sub(2)S over days to weeks.
Details
- Title: Subtitle
- Long-term release of a thiobenzamide from a backbone functionalized poly(lactic acid)
- Creators
- Tyler R LongAmaraporn WongrakpanichAnh-Vu DoAliasger K SalemNed B Bowden
- Resource Type
- Journal article
- Publication Details
- Polymer chemistry, Vol.6(40), pp.7188-7195
- DOI
- 10.1039/c5py01059d
- PMID
- 26870159
- PMCID
- PMC4746005
- NLM abbreviation
- Polym Chem
- ISSN
- 1759-9954
- eISSN
- 1759-9962
- Grant note
- DOI: 10.13039/100000165, name: Division of Chemistry, award: CHE-1213325; DOI: 10.13039/100000054, name: National Cancer Institute, award: 1R21CA13345-01/ 1R21CA128414-01A2/UI Mayo Clinic L; DOI: 10.13039/100000048, name: American Cancer Society, award: RSG-09-015-01-CDD
- Language
- English
- Date published
- 10/01/2015
- Academic Unit
- Roy J. Carver Department of Biomedical Engineering; Pharmaceutical Sciences and Experimental Therapeutics; Craniofacial Anomalies Research Center; Chemistry; Dental Research; Chemical and Biochemical Engineering
- Record Identifier
- 9983985708702771
Metrics
12 Record Views