Protein-induced fluorescence enhancement of two-photon excitable water-soluble diketopyrrolopyrroles

Document Type

Article

Publication Date

1-1-2017

Abstract

Fluorescent contrast agents are important tools in cell biology and medical imaging due to their high sensitivity and relative availability. Diketopyrrolopyrrole (DPP) derivatives have been recently studied for applications in bioimaging, but certain drawbacks due to their inherent structure have stifled progress towards their widespread implementation. Aggregation caused quenching (ACQ) associated with π-π stacking in relatively rigid extended conjugation systems as well as hydrophobicity of previously reported DPPs make most unsuitable for biological imaging applications. Addressing these deficiencies, we report the synthesis and photophysical characterization of two new water-soluble diketopyrrolopyrole (DPP) probes that exhibit pronounced protein-induced fluorescence enhancement (PIFE) upon binding serum albumin protein. In vitro studies were also performed showing low cytotoxicity for the new DPP probes. Two-photon fluorescence microscopy (2PFM) images were obtained via excitation at 810 nm and emission in the NIR window of biological transparency, illustrating the potential of these compounds as nonlinear optical bioimaging probes.

Identifier

85027224745 (Scopus)

Publication Title

Organic and Biomolecular Chemistry

External Full Text Location

https://doi.org/10.1039/c7ob01397c

ISSN

14770520

PubMed ID

28745371

First Page

6511

Last Page

6519

Issue

31

Volume

15

Grant

CBET-1517273

Fund Ref

National Science Foundation

This document is currently not available here.

Share

COinS