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Fluorogenic, two-photon-triggered photoclick chemistry in live mammalian cells.

ABSTRACT: The tetrazole-based photoclick chemistry has provided a powerful tool to image proteins in live cells. To extend photoclick chemistry to living organisms with improved spatiotemporal control, here we report the design of naphthalene-based tetrazoles that can be efficiently activated by two-photon excitation with a 700 nm femtosecond pulsed laser. A water-soluble, cell-permeable naphthalene-based tetrazole was identified that reacts with acrylamide with the effective two-photon cross-section for the cycloaddition reaction determined to be 3.8 GM. Furthermore, the use of this naphthalene-tetrazole for real-time, spatially controlled imaging of microtubules in live mammalian cells via the fluorogenic, two-photon-triggered photoclick chemistry was demonstrated.

SUBMITTER: Yu Z

PROVIDER: S-EPMC3866799 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

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Fluorogenic, two-photon-triggered photoclick chemistry in live mammalian cells.

Yu Zhipeng Z Ohulchanskyy Tymish Y TY An Peng P Prasad Paras N PN Lin Qing Q

Journal of the American Chemical Society 20131031 45

The tetrazole-based photoclick chemistry has provided a powerful tool to image proteins in live cells. To extend photoclick chemistry to living organisms with improved spatiotemporal control, here we report the design of naphthalene-based tetrazoles that can be efficiently activated by two-photon excitation with a 700 nm femtosecond pulsed laser. A water-soluble, cell-permeable naphthalene-based tetrazole was identified that reacts with acrylamide with the effective two-photon cross-section for ...[more]

PMID: 24168622

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