Issue 28, 2019

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

Abstract

Supramolecular host–guest pairs, with a very high association constant, represent excellent molecular recognition motifs, and serve as useful building blocks for numerous exciting supramolecular functional materials. Cyclodextrins, an important class of glucopyranose-based hosts, generally, suffer from low affinity for most guest molecules (102–104 M−1). Herein, we report a styryl-based fluorogenic probe which registers a very high association constant of 7.84 × 105 M−1 with sulfobutylether substituted β-cyclodextrin in contrast to a low association constant of 1.89 × 102 M−1 with unmodified β-cyclodextrin (β-CD). This exceptionally high binding affinity of the fluorogenic probe with the sulfobutylether substituted β-CD has been attributed to the strong electrostatic interactions between the cationic guest and the polyanionic host along with improved hydrophobic interactions due to the extended butylether groups present on the rims of the cyclodextrin cavity. The significant modulations in the photophysical properties of guest molecule, upon interaction with host molecule, have been investigated, in detail, using ground-state absorption, steady-state fluorescence and time-resolved emission measurements. The effect of temperature and ionic strength of the medium have been employed to investigate the nature of the underlying interactions in the present host–guest system. The possibility of indicator displacement assay involving the present host–guest system has also been demonstrated using a competitive binder.

Graphical abstract: A styryl based fluorogenic probe with high affinity for a cyclodextrin derivative

Supplementary files

Article information

Article type
Paper
Submitted
14 Jun 2019
Accepted
25 Jun 2019
First published
26 Jun 2019

Org. Biomol. Chem., 2019,17, 6895-6904

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

G. Chakraborty, A. K. Ray, P. K. Singh and H. Pal, Org. Biomol. Chem., 2019, 17, 6895 DOI: 10.1039/C9OB01349K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements