Tetramethylrhodamine is an essential scaffold of azide probe in detecting cellular acrolein

Ambara R Pradipta; Motoko Fujii; Tomonori Tanei; Koji Morimoto; Kenzo Shimazu; Shinzaburo Noguchi; Katsunori Tanaka

doi:10.1016/j.bmc.2019.04.026

Tetramethylrhodamine is an essential scaffold of azide probe in detecting cellular acrolein

Bioorg Med Chem. 2019 Jun 1;27(11):2228-2234. doi: 10.1016/j.bmc.2019.04.026. Epub 2019 Apr 20.

Authors

Ambara R Pradipta¹, Motoko Fujii¹, Tomonori Tanei², Koji Morimoto¹, Kenzo Shimazu², Shinzaburo Noguchi², Katsunori Tanaka³

Affiliations

¹ Biofunctional Synthetic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
² Department of Breast and Endocrine Surgery, Graduate School of Medicine, Osaka University, 2-2-E10 Yamadaoka, Suita, Osaka 565-0871, Japan.
³ Biofunctional Synthetic Chemistry Laboratory, RIKEN Cluster for Pioneering Research, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan; Biofunctional Chemistry Laboratory, A. Butlerov Institute of Chemistry, Kazan Federal University, 18 Kremlyovskaya Street, Kazan 420008, Russian Federation; GlycoTargeting Research Laboratory, RIKEN Baton Zone Program, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan. Electronic address: kotzenori@riken.jp.

PMID: 31023557
DOI: 10.1016/j.bmc.2019.04.026

Abstract

Tetramethylrhodamine (TAMRA)-phenyl azide is a chemical probe used to detect intracellular acrolein directly in live cells. Herein, we demonstrated that TAMRA is the optimum fluorophore for the probe. TAMRA-phenyl azide was used to reveal that high levels of acrolein are generated in a variety of breast cancer cells, regardless of the tumor subtype. These findings corroborate the analysis presented in our previous report, in which TAMRA-phenyl azide was used to label breast cancer tissues resected from breast cancer patients. Because high levels of acrolein were generated in all cancer cell types, we believe that acrolein detection may be useful as a general method for labeling cancerous tissues.

Keywords: 1,3-Dipolar cycloaddition; Acrolein; Breast cancer cell lines; Phenyl azide; TAMRA.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acrolein / analysis*
Acrolein / chemistry
Azides / chemistry*
Biomarkers / analysis
Biomarkers / chemistry
Breast Neoplasms / diagnostic imaging
Cell Line, Tumor
Cycloaddition Reaction
Fluorescent Dyes / chemistry*
Humans
Microscopy, Fluorescence / methods
Oxidative Stress
Rhodamines / chemistry*

Substances

Azides
Biomarkers
Fluorescent Dyes
Rhodamines
tetramethylrhodamine
Acrolein