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Related Experiment Video

Updated: Jan 22, 2026

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A styryl based fluorogenic probe with high affinity for a cyclodextrin derivative.

Goutam Chakraborty1, Alok K Ray1, Prabhat K Singh2

  • 1Laser and Plasma Technology Division, Bhabha Atomic Research Centre, Mumbai 400085, India and Homi Bhabha National Institute, Anushaktinagar, Mumbai 400094, India. prabhatk@barc.gov.in hpal@barc.gov.in.

Organic & Biomolecular Chemistry
|July 5, 2019
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Summary

A novel fluorogenic probe exhibits significantly enhanced binding affinity with modified cyclodextrins, enabling advanced supramolecular materials. This high affinity is driven by electrostatic and hydrophobic interactions, improving molecular recognition capabilities.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Chemical Sensing

Background:

  • Supramolecular host-guest chemistry utilizes molecular recognition for functional materials.
  • Cyclodextrins (CDs) are common hosts but often exhibit low guest affinity.
  • High-affinity host-guest systems are crucial for advanced applications.

Purpose of the Study:

  • To develop a fluorogenic probe with high affinity for modified cyclodextrins.
  • To investigate the binding interactions and photophysical changes in the host-guest system.
  • To explore the potential of this system in indicator displacement assays.

Main Methods:

  • Synthesis of a styryl-based fluorogenic probe.
  • Binding studies with unmodified and sulfobutylether-substituted β-cyclodextrin (β-CD).
  • Photophysical characterization using absorption, fluorescence, and time-resolved emission spectroscopy.
  • Investigation of temperature and ionic strength effects.
  • Demonstration of indicator displacement assay.

Main Results:

  • The probe showed a 7.84 × 10^5 M^-1 association constant with modified β-CD, versus 1.89 × 10^2 M^-1 with unmodified β-CD.
  • High affinity is attributed to strong electrostatic and enhanced hydrophobic interactions.
  • Significant changes in probe's photophysical properties upon binding were observed.
  • Binding interactions were confirmed to be sensitive to temperature and ionic strength.

Conclusions:

  • Sulfobutylether-substituted β-CD forms a high-affinity host-guest complex with the styryl-based fluorogenic probe.
  • The enhanced binding is driven by specific electrostatic and hydrophobic interactions.
  • This system demonstrates potential for sensitive molecular recognition and sensing applications.