A new class of ratiometric small molecule intracellular pH sensors for Raman microscopy

The Analyst
Liam T WilsonNicholas C O Tomkinson

Abstract

Intracellular pH (pHi) homeostasis is intertwined with a myriad of normal cellular behaviors as well as pathological processes. As such, small molecule probes for the measurement of pHi are invaluable tools for chemical biology, facilitating the study of the role of pH in cellular function and disease. The field of small molecule pHi sensors has traditionally been dominated with probes based on fluorescent scaffolds. In this study, a series of low molecular weight (<260) oligoyne compounds have been developed which exhibit pH sensitive alkyne stretching frequencies (νalkyne) in Raman spectroscopy. The modular design of the compounds enabled tuneability of their pKa(H) through simple structural modification, such that continuous pH sensitivity is achieved over the range 2-10. Alkyne stretching bands reside in the 'cell-silent' region of the Raman spectrum (1800-2600 cm-1) and are readily detectable in a cellular environment with subcellular spatial resolution. This enabled the application of a pH sensitive oligoyne compound to the ratiometric sensing of pHi in prostate cancer (PC3) cells in response to drug treatment. We propose that probes based on Alkyne Tag Raman Imaging offer an entirely new platform for the sensing of pHi, ...Continue Reading

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Citations

Oct 30, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jonathan HiraChristian S Lentz
Nov 5, 2020·Chemical Communications : Chem Comm·William J TippingDuncan Graham
Apr 7, 2021·Journal of Medicinal Chemistry·Adriana AdamczykMalgorzata Baranska
Sep 11, 2021·Analytical Chemistry·Liam T WilsonNicholas C O Tomkinson
Nov 5, 2021·Chemical Communications : Chem Comm·Sian Sloan-DennisonKaren Faulds

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Methods Mentioned

BETA
acetylation
Surface Enhanced Raman Scattering
Raman
Stimulated Raman Scattering
Raman microscopy
imaging techniques

Software Mentioned

ImageJ
Gaussian09
MATLAB® script
Excel
OriginPro
OriginPro2018
MATLAB®

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