Long-Wavelength, Photostable, Two-Photon Excitable BODIPY Fluorophores Readily Modifiable for Molecular Probes

    Authors

    X. F. Zhang; Y. Xiao; J. Qi; J. L. Qu; B. Kim; X. L. Yue;K. D. Belfield

    Comments

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    Abbreviated Journal Title

    J. Org. Chem.

    Keywords

    FLUORESCENT-PROBE; LIVING CELLS; AZA-BODIPY; METAL-IONS; DYES; BORONDIPYRROMETHENE; DERIVATIVES; ABSORPTION; BORON; MITOCHONDRIA; Chemistry, Organic

    Abstract

    Near-infrared (NIR) fluorescent probes are increasingly popular in biological imaging and sensing, as long-wavelength (650-900 nm) excitation and emission have the advantages of minimum photodamage, deep tissue penetration, and minimum interference from autofluorescence in living systems. Here, a series of long-wavelength BODIPY dyes SPC, DC-SPC, DPC, and DC-DPC are synthesized conveniently and efficiently. They exhibit excellent photo-physical properties in far red to near-infrared region, including large extinction coefficients, high fluorescence quantum yields, good photostability, and reasonable two-photon absorption cross section. Comparison of single-molecular imaging confirms that DPC is a much more efficient and more photostable NIR fluorophore than the commonly used Cy5. Also importantly, two kinds of convenient functionalization sites have been reserved: the aryl iodide for organometallic couplings and the terminal alkyne groups for click reactions. Further derivatives DC-SPC-PPh3 exhibit specificity to localize in mitochondria. The introduction of triphenylphosphonium (TPP) moieties mediates its hydrophilic lipophilic balance and makes DC-SPC-PPh3 appropriate for cell labeling. Their long-wavelength emission at similar to 650 nm can efficiently avoid the spectral crosstalk with other probes emitting in the visible light region. Superior photostability, low cytotoxicity, and two-photon excitable properties demonstrate its utility as a standard colocalizing agent to estimate the other probes' local distribution.

    Journal Title

    Journal of Organic Chemistry

    Volume

    78

    Issue/Number

    18

    Publication Date

    1-1-2013

    Document Type

    Article

    Language

    English

    First Page

    9153

    Last Page

    9160

    WOS Identifier

    WOS:000330159500023

    ISSN

    0022-3263

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