Homobifunctional Photocaged 2-Butene-1,4-dials (bis-PBDAs) as Amino-Reactive Photo-Crosslinkers for Biomaterial Fabrication and Cell Fixation

Chembiochem. 2025 Apr 14;26(8):e202500033. doi: 10.1002/cbic.202500033. Epub 2025 Feb 12.

Abstract

Crosslinking amine-rich biomolecules with aldehydes, such as paraformaldehyde (PFA) and glutaraldehyde (GA), is a widely used method for biomaterial fabrication and cell fixation. In this study, we introduce homobifunctional photocaged 2-butene-1,4-dials (bis-PBDAs) as novel amine-reactive photo-crosslinkers. Compared to PFA and GA, bis-PBDAs are inherently less toxic. Upon photo-deprotection, bis-PBDAs efficiently react with the amino groups of biomolecules, such as carboxymethyl chitosan and histone H3, forming stable, well-defined crosslinks. Even at low concentrations (~100 μM), bis-PBDAs facilitate effective cell fixation without significantly altering cellular morphology or interfering with biochemical analyses, including protein/mRNA extraction and immunofluorescence imaging. Therefore, bis-PBDAs are promising reagents for crosslinking amine-rich biopolymers and hold great potential in biomaterial fabrication and the fixation of living cells and tissues.

Keywords: Amine-rich biomolecules; Cell fixation; Hydrogel; Photo-crosslinker.

MeSH terms

  • Amines / chemistry
  • Animals
  • Biocompatible Materials* / chemistry
  • Chitosan / analogs & derivatives
  • Chitosan / chemistry
  • Cross-Linking Reagents* / chemistry
  • Glutaral / chemistry
  • Humans
  • Molecular Structure
  • Photochemical Processes

Substances

  • Cross-Linking Reagents
  • Biocompatible Materials
  • Amines
  • Glutaral
  • Chitosan