Issue 12, 2015

A novel rhodamine-3,4-dihydro-2H-1,3-benzoxazine conjugate as a highly sensitive and selective chemosensor for Fe3+ ions with cytoplasmic cell imaging possibilities

Abstract

A novel, highly sensitive and selective fluorescent chemosensor ‘rhodamine-3,4-dihydro-2H-1,3-benzoxazine’ [RH-BZN (1)] has been synthesized and characterized by single crystal X-ray diffraction and other physicochemical techniques. In 3 : 7 water : MeCN (v/v) at pH 7.2 (10 mM HEPES buffer, μ = 0.05 M LiCl) it selectively recognizes Fe3+ through 1 : 1 complex formation resulting in a 240-fold fluorescence enhancement and a binding constant (Kf) of 1.50 × 104 M−1. The otherwise non-fluorescent spirolactam form of the probe results in dual changes in absorbance and fluorescence arising out of opening of the spirolactam ring through coordination to Fe3+ ions. This probe could suitably be employed for cytoplasmic intracellular imaging of Fe3+ without notable cytotoxicity. The reversible binding of RH-BZN to Fe3+ was confirmed by reacting with tetra-n-butylammonium fluoride both in extra- and intra-cellular conditions.

Graphical abstract: A novel rhodamine-3,4-dihydro-2H-1,3-benzoxazine conjugate as a highly sensitive and selective chemosensor for Fe3+ ions with cytoplasmic cell imaging possibilities

Supplementary files

Article information

Article type
Paper
Submitted
21 Mar 2015
Accepted
08 May 2015
First published
11 May 2015

Anal. Methods, 2015,7, 5149-5156

Author version available

A novel rhodamine-3,4-dihydro-2H-1,3-benzoxazine conjugate as a highly sensitive and selective chemosensor for Fe3+ ions with cytoplasmic cell imaging possibilities

H. A. Molla, R. Bhowmick, A. Katarkar, K. Chaudhuri, S. Gangopadhyay and M. Ali, Anal. Methods, 2015, 7, 5149 DOI: 10.1039/C5AY00754B

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