Issue 1, 2014

A novel strategy to design latent ratiometric fluorescent pH probes based on self-assembled SNARF derivatives

Abstract

In this study, we describe a rational design strategy to develop a latent ratiometric fluorescent pH probe from self-assembled seminaphthorhodafluor (SNARF) derivatives in aqueous conditions. Analysis of the characteristics of SNARF derivatives with protected phenolic groups allowed classification of the threshold between the assembled and monomeric states according to the Hansch–Fujita hydrophobic parameters for a substituent inserted as a SNARF-OH phenolic-protecting group. The esterase-activated latent ratiometric fluorescent pH probe SNARF-OBn(OAc) was characterized in the application of tuneable small-molecule aggregation and disaggregation. Before esterase treatment, SNARF-OBn(OAc) formed self-assembled clusters, emitting no fluorescence. The significant fluorescence was observed after esterase treatment because the self-assembled clusters of SNARF-OBn(OAc) diffuse as SNARF-OH monomers, demonstrating the intracellular application of SNARF-OBn(OAc) as a latent ratiometric fluorescent pH probe for floating cells. Furthermore, to directly visualize the state of self-assembled SNARF derivatives for investigating the mechanism of their cellular uptake, SNARF-Dan was rationally designed and applied for cellular imaging. Through the cellular application of SNARF-Dan, it was suggested that the self-assembled SNARF derivatives were introduced into the cell via macropinocytosis.

Graphical abstract: A novel strategy to design latent ratiometric fluorescent pH probes based on self-assembled SNARF derivatives

Supplementary files

Article information

Article type
Paper
Submitted
26 7 2013
Accepted
24 10 2013
First published
28 10 2013

RSC Adv., 2014,4, 348-357

A novel strategy to design latent ratiometric fluorescent pH probes based on self-assembled SNARF derivatives

E. Nakata, Y. Yukimachi, Y. Nazumi, M. Uwate, H. Maseda, Y. Uto, T. Hashimoto, Y. Okamoto, H. Hori and T. Morii, RSC Adv., 2014, 4, 348 DOI: 10.1039/C3RA43928C

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