Synthesis, characterisation, and evaluation of a cross-linked disulphide amide-anhydride-containing polymer based on cysteine for colonic drug delivery

Vuanghao Lim, Kok Khiang Peh, Shariza Sahudin

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The use of disulphide polymers, a low redox potential responsive delivery, is one strategy for targeting drugs to the colon so that they are specifically released there. The objective of this study was to synthesise a new cross-linked disulphide-containing polymer based on the amino acid cysteine as a colon drug delivery system and to evaluate the efficiency of the polymers for colon targeted drug delivery under the condition of a low redox potential. The disulphide cross-linked polymers were synthesised via air oxidation of 1,2-ethanedithiol and 3-mercapto-N-2-(3-mercaptopropionamide)-3-mercapto propionic anhydride (trithiol monomers) using different ratio combinations. Four types of polymers were synthesised: P10, P11, P151, and P15. All compounds synthesised were characterised by NMR, IR, LC-MS, CHNS analysis, Raman spectrometry, SEM-EDX, and elemental mapping. The synthesised polymers were evaluated in chemical reduction studies that were performed in zinc/acetic acid solution. The suitability of each polymer for use in colon-targeted drug delivery was investigated in vitro using simulated conditions. Chemical reduction studies showed that all polymers were reduced after 0.5-1.0 h, but different polymers had different thiol concentrations. The bacterial degradation studies showed that the polymers were biodegraded in the anaerobic colonic bacterial medium. Degradation was most pronounced for polymer P15. This result complements the general consensus that biodegradability depends on the swellability of polymers in an aqueous environment. Overall, these results suggest that the cross-linked disulphide-containing polymers described herein could be used as coatings for drugs delivered to the colon.

Original languageEnglish
Pages (from-to)24670-24691
Number of pages22
JournalInternational Journal of Molecular Sciences
Volume14
Issue number12
DOIs
Publication statusPublished - 18 Dec 2013
Externally publishedYes

Fingerprint

Anhydrides
cysteine
disulfides
anhydrides
Drug delivery
Amides
Disulfides
amides
Cysteine
delivery
Polymers
drugs
evaluation
polymers
synthesis
Pharmaceutical Preparations
Colon
Drug Delivery Systems
Oxidation-Reduction
degradation

Keywords

  • Amide-anhydride
  • Colon drug delivery
  • Cysteine
  • Disulphide cross-linked polymer
  • Synthesis

ASJC Scopus subject areas

  • Computer Science Applications
  • Molecular Biology
  • Catalysis
  • Inorganic Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Synthesis, characterisation, and evaluation of a cross-linked disulphide amide-anhydride-containing polymer based on cysteine for colonic drug delivery. / Lim, Vuanghao; Khiang Peh, Kok; Sahudin, Shariza.

In: International Journal of Molecular Sciences, Vol. 14, No. 12, 18.12.2013, p. 24670-24691.

Research output: Contribution to journalArticle

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