Rhodamine-based fluorescent and colorimetric sensor for zinc and its application in bioimaging

Wechakorn, Kanokorn; Suksen, Kanoknetr; Piyachaturawat, Pawinee; Kongsaeree, Palangpon

doi:10.1016/j.snb.2016.01.045

Cited by 88 publications

(15 citation statements)

References 39 publications

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“…Rhodamine hydrazide‐propargyl conjugate was synthesized using a previously reported procedure . Rhodamine hydrazide (182.6 mg, 0.40 mmol) and anhydrous K 2 CO 3 (110.6 mg, 0.80 mmol) and KI (6.6 mg, 0.04 mmol) was dissolved in MeCN (30 ml) with vigorous stirring.…”

Section: Methodsmentioning

confidence: 99%

“…The designed chemical probe RHT was prepared using a previously reported procedure . To a solution of propargyl‐rhodamine conjugate (99.3 mg, 0.2 mmol) in acetone was added CuBr(PPh 3 ) 3 (9.7 mg, 0.01 mmol) and benzyl azide (29.3 mg, 0.22 mmol) at room temperature with stirring for 6 h. The product was purified by column chromatography to obtain 107.2 mg of the desired RHT as a brown solid (85.4% yield).…”

Section: Methodsmentioning

confidence: 99%

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A rhodamine‐triazole fluorescent chemodosimeter for Cu²⁺ detection and its application in bioimaging

et al. 2017

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A rhodamine-based fluorescent chemodosimeter rhodamine hydrazide-triazole (RHT) tethered with a triazole moiety was developed for Cu 2+ detection. In aqueous medium, the RHT probe exhibited high selectivity and sensitivity toward Cu 2+ among other metal ions. The addition of Cu 2+ triggered a fluorescence emission of RHT by 384-fold (Φ = 0.33) based on a ring-opening process and a subsequent hydrolysis reaction. Moreover, RHT also showed a selective colorimetric response toward Cu 2+ from colorless solution to pink, readily observed with the naked eye.The limit of detection of RHT for Cu 2+ was calculated to be 1 nM (0.06 ppb). RHT was successfully demonstrated to detect Cu 2+ in Chang liver cells by confocal fluorescence microscopy.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

A rhodamine‐triazole fluorescent chemodosimeter for Cu²⁺ detection and its application in bioimaging

et al. 2017

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“…So there is redshift of 49 nm in the absorption spectrum, while for the emission spectrum, it is 17 nm. With other metal ions, such as Na + , K + , Mn 2+ , Fe 3+ , Co 2+ , Ni 2+ , Cu 2+ , Ag + , Cd 2+ , and Hg 2+ , there is no significant enhancement in the emission intensity (Figure ), and so, the observed enhancement in fluorescence could be due to photoinduced‐electron‐transfer (PET) quenching between the chelating unit and the fluorophore , , . As the concentration of zinc ions is increased, there is enhancement in the fluorescence of HL1 , as can be seen in Figures and S8; this could be due to an equilibrium between the free and bound zinc ions with the ligand.…”

Section: Resultsmentioning

confidence: 93%

Purine‐Based Fluorescent Sensors for Imaging Zinc Ions in HeLa Cells

et al. 2017

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We synthesized three chelate‐tethered purine ligands, having a Schiff base linkage at the N9 position, which resulted in the dipolar imine‐methoxyphenol adenine Schiff base HL1, the 2‐aminopurine Schiff base HL2, and the 2,6‐diaminopurine Schiff base HL3. These ligands selectively showed enhancement of the fluorescence of the zinc ions. The imine‐based compound HL1 chelated with zinc ions to give the discrete dimeric structure 1, a green fluorescent complex, which was again stabilized by purine–purine interactions to give a 1D polymeric structure. The ligands having a 6‐amino group, HL1 and HL3, have high quantum yield, which gives higher fluorescence enhancement of the free zinc ions in the HeLa cells. HL1 was localized in the cytoplasm and the nucleoli of the HeLa cells, which was confirmed by an RNase digestion test.

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“…In recent years, several fluorescent probes for Zn 2+ ion have been developed, some of which, for example, were turn‐on rhodamine‐based fluorescent sensors containing bis‐triazolyl moieties for Zn 2+ detection among various other metal ions and that had a detection limit of 1 M for application in in vitro HeLa cell imaging . A fluorescent, colorimetric sensor based on 8‐aminoquinoline for Zn 2+ detection in living cells through internal charge transfer (ICT) and chelation‐enhanced fluorescence mechanisms has been described previously .…”

Section: Introductionmentioning

confidence: 99%

Phenothiazine–rhodamine‐based colorimetric and fluorogenic ‘turn‐on' sensor for Zn²⁺ and bioimaging studies in live cells

et al. 2019

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A phenothiazine-rhodamine (PTRH) fluorescent dyad was synthesized and its ability to selectively sense Zn 2+ ions in solution and in in vitro cell lines was tested using various techniques. When compared with other competing metal ions, the PTRH probe showed the high selectivity for Zn 2+ ions that was supported by electronic and emission spectral analyses. The emission band at 528 nm for the PTRH probe indicated the ring closed form of PTRH, as for Zn 2+ ion binding to PTRH, the λ em get shift to 608 nm was accompanied by a pale yellow to pink colour (under visible light) and green to pinkish red fluorescence emission (under UV light) due to ring opening of the spirolactam moiety in the PTRH ligand. Spectral overlap of the donor emission band and the absorption band of the ring opened form of the acceptor moiety contributed towards the fluorescence resonance energy transfer ON mechanism for Zn 2+ ion detection. The PTRH sensor had the lowest detection limit for Zn 2+ , found to be 2.89 × 10 −8 M. The sensor also demonstrated good sensing application with minimum toxicity for in vitro analyses using HeLa cells.

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Rhodamine-based fluorescent and colorimetric sensor for zinc and its application in bioimaging

Cited by 88 publications

References 39 publications

A rhodamine‐triazole fluorescent chemodosimeter for Cu²⁺ detection and its application in bioimaging

A rhodamine‐triazole fluorescent chemodosimeter for Cu²⁺ detection and its application in bioimaging

Purine‐Based Fluorescent Sensors for Imaging Zinc Ions in HeLa Cells

Phenothiazine–rhodamine‐based colorimetric and fluorogenic ‘turn‐on' sensor for Zn²⁺ and bioimaging studies in live cells

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Rhodamine-based fluorescent and colorimetric sensor for zinc and its application in bioimaging

Cited by 88 publications

References 39 publications

A rhodamine‐triazole fluorescent chemodosimeter for Cu2+ detection and its application in bioimaging

A rhodamine‐triazole fluorescent chemodosimeter for Cu2+ detection and its application in bioimaging

Purine‐Based Fluorescent Sensors for Imaging Zinc Ions in HeLa Cells

Phenothiazine–rhodamine‐based colorimetric and fluorogenic ‘turn‐on' sensor for Zn2+ and bioimaging studies in live cells

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A rhodamine‐triazole fluorescent chemodosimeter for Cu²⁺ detection and its application in bioimaging

A rhodamine‐triazole fluorescent chemodosimeter for Cu²⁺ detection and its application in bioimaging

Phenothiazine–rhodamine‐based colorimetric and fluorogenic ‘turn‐on' sensor for Zn²⁺ and bioimaging studies in live cells