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103 Publications

Showing 101-103 of 103 results
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    11/18/11 | Facile and general synthesis of photoactivatable xanthene dyes.
    Wysocki LM, Grimm JB, Tkachuk AN, Brown TA, Betzig E, Lavis LD
    Angewandte Chemie. 2011 Nov 18;50:11206-9. doi: 10.1002/anie.201104571

    Despite the apparent simplicity of the xanthene fluorophores, the preparation of caged derivatives with free carboxy groups remains a synthetic challenge. A straightforward and flexible strategy for preparing rhodamine and fluorescein derivatives was developed using reduced, “leuco” intermediates.

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    02/01/11 | Histochemistry: live and in color.
    Lavis LD
    The Journal of Histochemistry and Cytochemistry: Official Journal of the Histochemistry Society. 2011 Feb;59:139-45. doi: 10.1369/0022155410395760

    Histochemistry (chemistry in the context of biological tissue) is an invaluable set of techniques used to visualize biological structures. This field lies at the interface of organic chemistry, biochemistry, and biology. Integration of these disciplines over the past century has permitted the imaging of cells and tissues using microscopy. Today, by exploiting the unique chemical environments within cells, heterologous expression techniques, and enzymatic activity, histochemical methods can be used to visualize structures in living matter. This review focuses on the labeling techniques and organic fluorophores used in live cells.

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    01/01/11 | Synthesis and utility of fluorogenic acetoxymethyl ethers.
    Lavis LD, Chao T, Raines RT
    Chemical Science. 2011 Jan 1;2(3):521-30. doi: 10.1039/C0SC00466A

    Phenolic fluorophores such as fluorescein, Tokyo Green, resorufin, and their derivatives are workhorses of biological science. Acylating the phenolic hydroxyl group(s) in these fluorophores masks their fluorescence. The ensuing ester is a substrate for cellular esterases, which can restore fluorescence. These esters are, however, notoriously unstable to hydrolysis, severely compromising their utility. The acetoxymethyl (AM) group is an esterase-sensitive motif that can mask polar functionalities in small molecules. Here, we report on the use of AM ether groups to mask phenolic fluorophores. The resulting profluorophores have a desirable combination of low background fluorescence, high chemical stability, and high enzymatic reactivity, both in vitro and in cellulo. These simple phenyl ether-based profluorophores could supplement or supplant the use of phenyl esters for imaging biochemical and biological systems.

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