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

    Authors: contact us about adding a copy of your work at [email protected]

    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

    Share

    COinS
     

    Accessibility Statement

    This item was created or digitized prior to April 24, 2027, or is a reproduction of legacy media created before that date. It is preserved in its original, unmodified state specifically for research, reference, or historical recordkeeping. In accordance with the ADA Title II Final Rule, the University Libraries provides accessible versions of archival materials upon request. To request an accommodation for this item, please submit an accessibility request form.