Donor-Acceptor-Donor Fluorene Derivatives for Two-Photon Fluorescence Lysosomal Imaging

    Authors

    S. Yao; H. Y. Ahn; X. H. Wang; J. Fu; E. W. Van Stryland; D. J. Hagan;K. D. Belfield

    Comments

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    Abbreviated Journal Title

    J. Org. Chem.

    Keywords

    ONE-PHOTON; FEMTOSECOND CONTINUUM; CROSS-SECTIONS; ABSORPTION; MICROSCOPY; EXCITATION; PHOTOSTABILITY; MOLECULES; DELIVERY; CANCER; Chemistry, Organic

    Abstract

    As part of a strategy to achieve large two-photon absorptivity in fluorene-based probes, a series of donor- acceptor-donor (D-A-D) type derivatives were synthesized and their two-photon absorption (2PA) properties investigated. The synthesis of D-A-D fluorophores was achieved by efficient preparation of key intermediates for the introduction of central electron acceptor groups. To accomplish the synthesis of two of the new derivatives, a high-yield method for a one-step direct dibromomethylation of phenyl sulfide was developed. The linear and nonlinear optical properties, including UV-vis absorption, fluorescence emission, fluorescence anisotropy, and two-photon absorption (2PA), of the new D-A-D compounds were measured and compared to their D-A or D-D counterparts. Fully conjugated acceptor moieties in the center of the D-A-D fluorophore led to the greatest increase in the 2PA cross section, while weakly conjugated central acceptors exhibited only a modest increase in the 2PA cross section relative to D-A diploar analogs. Encapsulation of the new probes in Pluronic F 108N F micelles, and subsequent incubation in HCT 116 cells, resulted in very high lysosomal colocalization ( > 0.98 colocalization coefficient) relative to commercial Lysotracker Red, making the micelle-encapsulated dyes particularly attractive as fluorescent probes for two-photon fluorescence microscopy lysosomal imaging.

    Journal Title

    Journal of Organic Chemistry

    Volume

    75

    Issue/Number

    12

    Publication Date

    1-1-2010

    Document Type

    Article

    Language

    English

    First Page

    3965

    Last Page

    3974

    WOS Identifier

    WOS:000278560700004

    ISSN

    0022-3263

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