Classical thiazole orange and its regioisomer as fluorogenic probes for nucleolar RNA imaging in living cells

Nishizawa, Seiichi; He, Min; Sato, Yusuke

doi:10.1039/d2an01804g

Cited by 7 publications

(2 citation statements)

References 63 publications

(90 reference statements)

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“…Our group also reported that TO worked as a fluorogenic dye for nucleolar RNA imaging in living cells ( Φ bound = 0.16). 23 The examination with synthetic RNA and DNA revealed that TO prefers RNA over DNA, with a significant response to double-stranded RNA (rG/rC and rA/rU) and single-stranded rG. 23 In addition, TO and its derivative (TO-PRO-1) were reported as indicators in the FID assay for targeting various RNA structures including TAR RNA and the bacterial ribosomal RNA A-site, 6,7 a being apparently characterized as non-selective for TAR RNA.…”

Section: Resultsmentioning

confidence: 99%

“…23 The examination with synthetic RNA and DNA revealed that TO prefers RNA over DNA, with a significant response to double-stranded RNA (rG/rC and rA/rU) and single-stranded rG. 23 In addition, TO and its derivative (TO-PRO-1) were reported as indicators in the FID assay for targeting various RNA structures including TAR RNA and the bacterial ribosomal RNA A-site, 6,7 a being apparently characterized as non-selective for TAR RNA. Apparently, our FiLuP probe does function distinctly from the previous Tat peptide-based probes 8,11,12 as well as TO itself, having prominent binding and fluorescence properties toward TAR RNA.…”

Section: Resultsmentioning

confidence: 99%

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Forced intercalation-induced light-up peptides as fluorogenic indicators for the HIV-1 TAR RNA-ligand assay

Lee,

Sato,

Ujuagu

et al. 2024

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Forced intercalation-induced light-up peptides as fluorogenic indicators for the HIV-1 TAR RNA-ligand assay

Lee,

Sato,

Ujuagu

et al. 2024

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RNA‐Selective Small‐Molecule Ligands: Recent Advances in Live‐Cell Imaging and Drug Discovery

Chan,

Wang,

Zheng

et al. 2023

ChemMedChem

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RNA structures, including those formed from coding and noncoding RNAs, alternative to protein‐based drug targets, could be a promising target of small molecules for drug discovery against various human diseases, particularly in anticancer, antibacterial and antivirus development. The normal cellular activity of cells is critically dependent on the function of various RNA molecules generated from DNA transcription. Moreover, many studies support that mRNA‐targeting small molecules may regulate the synthesis of disease‐related proteins via the non‐covalent mRNA‐ligand interactions that do not involve gene modification. RNA‐ligand interaction is thus an attractive approach to address the challenge of “undruggable” proteins in drug discovery because the intracellular activity of these proteins is hard to be suppressed with small molecule ligands. We selectively surveyed a specific area of RNA structure‐selective small molecule ligands in fluorescence live cell imaging and drug discovery because the area was currently underexplored. This state‐of‐the‐art review thus mainly focuses on the research published within the past three years and aims to provide the most recent information on this research area; hopefully, it could be complementary to the previously reported reviews and give new insights into the future development on RNA‐specific small molecule ligands for live cell imaging and drug discovery.

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Nucleic Acid Specificity, Cellular Localization and Reduced Toxicities of Thiazole Orange‐Neomycin Conjugates

McFarland,

Fernando,

Kellish

et al. 2024

ChemistryOpen

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Selective binding of small molecule ligands to nucleic acids with high affinity and limited toxicity remains an important goal in the development of compounds that can probe DNA or RNA in cells. Thiazole orange is a cell semi‐permeant, fluorescent cyanine dye, with low background noise, that binds several forms of nucleic acids. However, thiazole orange can exhibit cytotoxicity when used at high concentration and/or with prolonged exposure. Neomycin is a non‐fluorescent antibiotic with affinity for several forms of nucleic acids, but does not readily enter mammalian cells. Conjugation of neomycin with thiazole orange can exploit the properties of each individual compound, yielding a small molecule that could be used for nontoxic application in cellular analysis by microscopic imaging. We demonstrate that conjugation of neomycin with thiazole orange increases the cell permeability of neomycin, decreases the cytotoxicity of thiazole orange, and exhibits a greater degree of intracellular RNA targeted localization in the nucleolus, when compared to thiazole orange. Relative to thiazole orange, the conjugated compounds showed a much higher degree of stabilization of the nucleic acids as reflected in a greater denaturation temperature. Ultimately, our studies indicate that the conjugated thiazole orange‐neomycin compounds can be used as an RNA targeted, less cytotoxic alternative for cellular labeling.

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Classical thiazole orange and its regioisomer as fluorogenic probes for nucleolar RNA imaging in living cells

Abstract: In contrast to well-established DNA-selective dyes for live cell imaging, RNA-selective dyes have been less developed due to the challenge to make small molecules have the RNA selectivity over DNA....

Cited by 7 publications

References 63 publications

Forced intercalation-induced light-up peptides as fluorogenic indicators for the HIV-1 TAR RNA-ligand assay

Forced intercalation-induced light-up peptides as fluorogenic indicators for the HIV-1 TAR RNA-ligand assay

RNA‐Selective Small‐Molecule Ligands: Recent Advances in Live‐Cell Imaging and Drug Discovery

Nucleic Acid Specificity, Cellular Localization and Reduced Toxicities of Thiazole Orange‐Neomycin Conjugates

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