A Palette of Minimally Tagged Sucrose Analogues for Real‐Time Raman Imaging of Intracellular Plant Metabolism

Abstract

Sucrose is the main saccharide used for longdistance transport in plants and plays an essential role in energy metabolism; however, there are no analogues for real-time imaging in live cells. We have optimised a synthetic approach to prepare sucrose analogues including very small (% 50 Da or less) Raman tags in the fructose moiety. Spectroscopic analysis identified the alkyne-tagged compound 6 as a sucrose analogue recognised by endogenous transporters in live cells and with higher Raman intensity than other sucrose derivatives. Herein, we demonstrate the application of compound 6 as the first optical probe to visualise real-time uptake and intracellular localisation of sucrose in live plant cells using Raman microscopy.

Miniaturized Chemical Tags for Optical Imaging

“…Reproduced with permission. [75] Copyright 2021 Wiley-VCH. E) Three-color multiplex imaging of EU- 13 C 2 (RNA), EdU-13 C (DNA) and 17-ODYA (fatty acids) using an alkyne isotopic editing strategy.…”

“… [74] Our group synthesized a collection of sucrose analogues, from which aminopropargyl sucrose was used for trafficking studies in live plant cells for the first time (Figure 5). [75] Furthermore, SRS microscopy of sialylated glycans using a similar tagging strategy has been reported [76] . In addition to alkynes, nitrile and isonitrile groups have also been employed as small Raman tags for metabolite detection, such as rhabduscin in bacteria [77] and the small molecule drug, neratinib [78] .…”

A decade of alkyne-tag Raman imaging (ATRI): applications in biological systems

“…For example, de Moliner et al reported real-time visualization of sucrose uptake in plant cells using an alkyne-tagged sucrose. 108 Coronatine, a bacterial virulence factor, resembles a plant hormone and can thus hijack the plant system. 109 Unfortunately, fluorescence-labelled coronatine loses its activity, but alkyne modification does not affect the activity.…”

“…For example, de Moliner et al reported real-time visualization of sucrose uptake in plant cells using an alkyne-tagged sucrose. 108 …”

Elucidating Gold–MnO2 Core–Shell Nanoenvelope for Real Time SERS-Guided Photothermal Therapy on Pancreatic Cancer Cells

“…It is worth mentioning that AuNPs are excellent substrates for surface-enhanced Raman spectroscopy (SERS), which is widely utilized for the precise monitoring of therapeutic progression through Raman fingerprints at the molecular level. − SERS attributes clear-cut molecular evidence that improves the selectivity, accuracy, and specificity of multiplex detection by avoiding spectral overlap, making it a reliable tool for molecular diagnostics . The high intensity signature Raman peaks from the SERS tags can provide in depth information regarding intercellular distribution. − Even though a number of Raman reporter molecules are well-known with excellent Raman cross-section, the problem associated with photobleaching remains as a bottleneck .…”