Deep-red fluorogenic cyanine dyes carrying an amino group-terminated side chain for improved RNA detection and nucleolar RNA imaging

Sato, Yusuke; Igarashi, Yugo; Suzuki, Motoo; Higuchi, Kei; Nishizawa, Seiichi

doi:10.1039/d1ra05872j

Cited by 10 publications

(18 citation statements)

References 22 publications

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“…The emission in the nucleolus is clearly observed and can be distinguishable from that in the nucleus. Several fluorescent probes have been so far shown to possess an imaging performance for nucleolar RNA in living cells better than that with SYTO RNA select; 7 − 11 , 21 however, to the best of our knowledge, nucleolar RNA imaging has never been accomplished at a 50 nM probe concentration. Thus, BIOP can work as the most sensitive imaging probe for nucleolar RNA in living cells.…”

Section: Resultsmentioning

confidence: 97%

“…This value is 1 order of magnitude larger compared to that of BIQ derivatives that were previously developed by us. 11 The brightness, defined as the product of the fluorescence quantum yield and molecular extinction coefficient, reaches 1.1 × 10 4 for BIOP bound to RNA ( Table 1 ). Apparently, the integration of the oxazolopyridine unit into the monomethine cyanine scaffold leads to large Φ bound value for RNA binding.…”

Section: Resultsmentioning

confidence: 99%

“…In addition, the response for RNA is larger than that for DNA ( Figure 1 ), which indicates the selective response of BIOP toward RNA like BIQ derivatives. 11 …”

Section: Resultsmentioning

confidence: 99%

“…For the synthesis of BIOP (Scheme ), 5-methyl-2-(methylthio)oxazolo[5,4- c ]pyridin-5-ium tosylate ( 2 ) was first prepared in three steps from the commercially available 4-aminopyridin-3-ol ( 1 ) (Scheme S1). , Compound 2 was then combined with the benzo[ c , d ]indole unit ( 3 ) , by a condensation reaction, which affords BIOP (purity >95%) as characterized by 1 H NMR and ESI-MS (Figures S1 and S2). Further details of the synthesis are shown in the Supporting Information.…”

Section: Resultsmentioning

confidence: 99%

“…It was reported that the viability of 3T3 cells was decreased to 70–75% with an incubation concentration of 5–20 μM P12 for 24 h. 10 Our group designed unsymmetrical monomethine cyanine-based probes with a distinct light-up switch for RNA. 11 Benzo[ c , d ]indole-quinoline (BIQ) showed a significant enhancement of the emission by more than 100-fold upon binding to RNA, 11a whose fluorogenic “off–on” ability in deep-red region (λ em > 650 nm) is outstanding among small probes for live-cell RNA imaging. We also demonstrated nucleolar RNA staining in living MCF7 cells even with 500 nM of the BIQ derivative with improved binding affinity.…”

Section: Introductionmentioning

confidence: 99%

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Bright and Light-Up Sensing of Benzo[c,d]indole-oxazolopyridine Cyanine Dye for RNA and Its Application to Highly Sensitive Imaging of Nucleolar RNA in Living Cells

et al. 2022

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Small molecular weight probes that can show a fluorescence signaling response upon binding to RNAs are promising for RNA imaging in living cells. Live-cell RNA imaging probes that can achieve a large light-up ability (>100-fold) and high Φ bound value for RNA (>0.50) have been rarely reported to date. Here, benzo[ c , d ]indole-oxazolopyridine (BIOP), an unsymmetrical monomethine cyanine analogue, was newly developed as a bright and large light-up probe for imaging of nucleolar RNA in living cells. BIOP served as a yellow-emissive probe (λ em = 570 nm) and exhibited a significant light-up response upon RNA binding (770-fold) with a high Φ bound value (0.52). We demonstrated the advantages of BIOP over a commercially available RNA-staining probe, SYTO RNA select, for robust and sensitive RNA sensing by a systematic comparison of fluorescent properties for RNA. In addition, BIOP was found to possess high membrane permeability and low cytotoxicity in living cells. The examination of live-cell imaging revealed that BIOP exhibited emission in the nucleolus upon binding to nucleolar RNA much stronger than that of SYTO RNA select. Furthermore, BIOP facilitated the highly sensitive imaging of nucleolar RNA, in which 50 nM BIOP can stain nucleolar RNA in living cells with a 20 min incubation.

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Section: Resultsmentioning

confidence: 97%

Section: Resultsmentioning

confidence: 99%

“…In addition, the response for RNA is larger than that for DNA ( Figure 1 ), which indicates the selective response of BIOP toward RNA like BIQ derivatives. 11 …”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Bright and Light-Up Sensing of Benzo[c,d]indole-oxazolopyridine Cyanine Dye for RNA and Its Application to Highly Sensitive Imaging of Nucleolar RNA in Living Cells

et al. 2022

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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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Benzo[c,d]Indole-Quinoline-Based Deep-Red Emissive Probes for Live-Cell Imaging of Nucleolar RNA

Suzuki,

Sato,

Nishizawa

2024

Methods in Molecular Biology

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Deep-red fluorogenic cyanine dyes carrying an amino group-terminated side chain for improved RNA detection and nucleolar RNA imaging

Abstract: The introduction of an amino-group-terminated side chain into deep-red emissive benzo[c,d]indole–quinoline monomethine cyanine dye has led to the improved detection of RNAs as well as the imaging of nucleolar RNAs in cells.

Cited by 10 publications

References 22 publications

Bright and Light-Up Sensing of Benzo[c,d]indole-oxazolopyridine Cyanine Dye for RNA and Its Application to Highly Sensitive Imaging of Nucleolar RNA in Living Cells

Bright and Light-Up Sensing of Benzo[c,d]indole-oxazolopyridine Cyanine Dye for RNA and Its Application to Highly Sensitive Imaging of Nucleolar RNA in Living Cells

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

Benzo[c,d]Indole-Quinoline-Based Deep-Red Emissive Probes for Live-Cell Imaging of Nucleolar RNA

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