Nitrocinnamate-functionalized gelatin: synthesis and "smart"hydrogel formation via photo-cross-linking

Biomacromolecules. 2005 May-Jun;6(3):1503-9. doi: 10.1021/bm049238w.

Abstract

Gelatin having p-nitrocinnamate pendant groups (Gel-NC) was prepared via an efficient one-pot synthesis, yield >87%. (1)H NMR data indicated that 1 mol of gelatin was modified with 18 +/- 6 mol of the photosensitive group. Upon exposure to low-intensity 365 nm UV light and in the absence of photoinitiators or catalysts, Gel-NC cross-linked within minutes into a gelatin-based hydrogel as monitored by UV-vis spectroscopy. The degree of swelling of this biodegradable hydrogel in aqueous solutions responded to changes in Gel-NC concentration levels, the ionic strength of the aqueous solutions, and photo-cross-linking time. Topography changes associated with phase transition resulting from "photocleavage" of the hydrogel network with 254 nm UV light were studied with AFM. Both Gel-NC and its hydrogel expressed low toxicity to human neonatal fibroblast cells. In addition, gelatin-based microgels were prepared via the photo-cross-linking of Gel-NC within inverse micelles.

Publication types

  • Comparative Study
  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Cinnamates / chemical synthesis*
  • Cinnamates / radiation effects
  • Cross-Linking Reagents / chemical synthesis*
  • Cross-Linking Reagents / radiation effects
  • Gelatin / chemical synthesis*
  • Gelatin / radiation effects
  • Hydrogels / chemical synthesis*
  • Hydrogels / radiation effects
  • Photic Stimulation / methods
  • Ultraviolet Rays*

Substances

  • Cinnamates
  • Cross-Linking Reagents
  • Hydrogels
  • Gelatin