Fabrication of deoxycholic acid tethered α-cyanostilbenes as smart low molecular weight gelators and AIEE probes for bio-imaging

Steroids. 2020 Aug:160:108659. doi: 10.1016/j.steroids.2020.108659. Epub 2020 May 18.

Abstract

Four novel deoxycholic acid tethered α-cyanostilbenes were designed, synthesized and characterized using detailed spectroscopic analysis. The synthesized deoxycholic acid tethered α-cyanostilbene derivatives formed stable gels with a variety of solvents, such as xylene, toluene, mesitylene, decane, dodecane etc. The stable gels showed lamellar sheet type structures stacked over each other, consisting of entangled fibres as evident from SEM, TEM and Fluorescence Microscopy images; The synthesized compounds exhibited AIEE behaviour in H2O/THF mixture, with the maximum emission observed in 70% H2O/THF fraction along with a bathochromic shift. A solvent thickening experiment was perform to establish the mechanism of AIEE and the AIEE property was explored for bacterial bio-imaging. The synthesized derivatized steroids proved their potential as multifunctional organic materials.

Keywords: AIEE; Bile acids; Bio-imaging; Gelation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylonitrile / analogs & derivatives*
  • Acrylonitrile / chemistry
  • Deoxycholic Acid / chemistry*
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Gels / chemical synthesis
  • Gels / chemistry
  • Microscopy, Fluorescence
  • Molecular Conformation
  • Molecular Imaging*
  • Molecular Weight
  • Serratia marcescens / isolation & purification*
  • Staphylococcus aureus / isolation & purification*

Substances

  • (Z)-2,3-diphenylacrylonitrile
  • Fluorescent Dyes
  • Gels
  • Deoxycholic Acid
  • Acrylonitrile