Scalable and Concise Synthesis of Dichlorofluorescein Derivatives Displaying Tissue Permeation in Live Zebrafish Embryos

Koide, Kazunori; Song, Fengling; Groh, Eric D. de; Garner, Amanda L.; Mitchell, Valerie D.; Davidson, Lance A.; Hukriede, Neil A.

doi:10.1002/cbic.200700565

Cited by 25 publications

(24 citation statements)

References 62 publications

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“…2) is as fluorescent as 2′,7′-dichlorofluorescein (DCF)21, when the phenolic hydroxy group is alkylated such compounds are nearly non-fluorescent22–27. Our hypothesis was that compound 4 , which was also predicted to be nearly non-fluorescent, would react with ozone, and the resulting aldehyde 6 would undergo β-elimination to yield the fluorescent compound 7 and acrolein (Fig.…”

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confidence: 99%

Specific fluorogenic probes for ozone in biological and atmospheric samples

et al. 2009

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Ozone exposure is a growing global health problem, especially in urban areas. While ozone in the stratosphere protects the earth from harmful ultraviolet light, tropospheric or ground-level ozone is toxic and can damage the respiratory tract. It has recently been shown that ozone may be produced endogenously in inflammation and antibacterial responses of the immune system; however, these results have sparked controversy owing to the use of a non-specific colorimetric probe. Here we report the synthesis of fluorescent molecular probes able to unambiguously detect ozone in both biological and atmospheric samples. Unlike other ozone-detection methods, in which interference from different reactive oxygen species is often a problem, these probes are ozone specific. Such probes will prove useful for the study of ozone in environmental science and biology, and so possibly provide some insight into the role of ozone in cells.

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confidence: 99%

Specific fluorogenic probes for ozone in biological and atmospheric samples

et al. 2009

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“…This high polarity confers substantial aqueous solubility, which is beneficial for some applications, such as protein labeling, but also results in low cellular permeability in assays involving living cells. Hydrophobic analogues of fluorescein such as Tokyo Green ( 2 ) [2], Pennsylvania Green ( 3 ) [3–4], and others [5] have been synthesized that replace a carboxylate with a methyl group or other less polar functionality. These hydrophobic analogues are generally more effective at penetrating cellular membranes [2,4].…”

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confidence: 99%

Hydrophobic analogues of rhodamine B and rhodamine 101: potent fluorescent probes of mitochondria in living C. elegans

Mottram¹,

Forbes²,

Ackley³

et al. 2012

Beilstein J. Org. Chem.

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SummaryMitochondria undergo dynamic fusion and fission events that affect the structure and function of these critical energy-producing cellular organelles. Defects in these dynamic processes have been implicated in a wide range of human diseases including ischemia, neurodegeneration, metabolic disease, and cancer. To provide new tools for imaging of mitochondria in vivo, we synthesized novel hydrophobic analogues of the red fluorescent dyes rhodamine B and rhodamine 101 that replace the carboxylate with a methyl group. Compared to the parent compounds, methyl analogues termed HRB and HR101 exhibit slightly red-shifted absorbance and emission spectra (5–9 nm), modest reductions in molar extinction coefficent and quantum yield, and enhanced partitioning into octanol compared with aqueous buffer of 10-fold or more. Comparison of living C. elegans (nematode roundworm) animals treated with the classic fluorescent mitochondrial stains rhodamine 123, rhodamine 6G, and rhodamine B, as well as the structurally related fluorophores rhodamine 101, and basic violet 11, revealed that HRB and HR101 are the most potent mitochondrial probes, enabling imaging of mitochondrial motility, fusion, and fission in the germline and other tissues by confocal laser scanning microscopy after treatment for 2 h at concentrations as low as 100 picomolar. Because transgenes are poorly expressed in the germline of these animals, these small molecules represent superior tools for labeling dynamic mitochondria in this tissue compared with the expression of mitochondria-targeted fluorescent proteins. The high bioavailabilty of these novel fluorescent probes may facilitate the identification of agents and factors that affect diverse aspects of mitochondrial biology in vivo.

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“…Next, we optimized conditions for a Hg(II)-promoted hydrolysis of vinyl ether 3 to form 1 33 in various buffers (for details, see Table S1, Supporting Information) at 25 °C. The ratio of Hg(II)-promoted and Hg(II)-free hydrolysis — the latter was negligible — was optimal at pH 3 (Figure 1a).…”

Section: Resultsmentioning

confidence: 99%

Development and Applications of Fluorogenic Probes for Mercury(II) Based on Vinyl Ether Oxymercuration

2011

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Mercury is a major threat to the environment and to human health. It is highly desirable to develop a user-friendly kit for on-site mercury detection. Such a method must be able to detect mercury below the threshold levels for drinking water, 1-2 ppb. We developed a fluorescence method based on the oxymercuration of vinyl ethers to detect mercury in dental and environmental samples. Chloride ions interfered with the oxymercuration reaction, but the addition of AgNO 3 solved this problem. Fine electronic and structural tuning led to the development of a more responsive probe that was less sensitive to chloride ion interference. This second generation probe could detect 1 ppb mercury ions in water.

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Scalable and Concise Synthesis of Dichlorofluorescein Derivatives Displaying Tissue Permeation in Live Zebrafish Embryos

Cited by 25 publications

References 62 publications

Specific fluorogenic probes for ozone in biological and atmospheric samples

Specific fluorogenic probes for ozone in biological and atmospheric samples

Hydrophobic analogues of rhodamine B and rhodamine 101: potent fluorescent probes of mitochondria in living C. elegans

Development and Applications of Fluorogenic Probes for Mercury(II) Based on Vinyl Ether Oxymercuration

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