A Series of Fluorene-Based Two-Photon Absorbing Molecules: Synthesis, Linear and Nonlinear Characterization, and Bioimaging

Andrade, Carlos Fernando Salgueirosa de; Yanez, Ciceron O.; Rodríguez, Luis G.; Belfield, Kevin D.

doi:10.1021/jo1005075

Cited by 69 publications

(49 citation statements)

References 30 publications

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“…To explore the utility of 1a as biolabel, an amine reactive derivative 1b was synthesized and conjugated to bovine serum albumin (BSA) 26. Featuring a further extended conjugation length, the 2PA cross section of fluorophores 2a and 2b improved to 248 GM (λ = 730 nm) and 563 GM (λ = 730 nm), respectively 27. Incubation of COS-7 and HCT 116 cells with 2a revealed a punctate staining pattern with a predominantly endosomal localization (Figure 3).…”

Section: Design Strategies For Cation-responsive Fluorescent Indicmentioning

confidence: 99%

Metal-Ion-Responsive Fluorescent Probes for Two-Photon Excitation Microscopy

2010

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Metal ion-responsive fluorescent probes are powerful tools for visualizing labile metal ion pools in live cells. To take full advantage of the benefits offered by two-photon excitation microscopy, including increased depth penetration, reduced phototoxicity, and intrinsic 3D capabilities, the photophysical properties of the probes must be optimized for nonlinear excitation. This review summarizes the challenges associated with the design of two-photon excitable fluorescent probes and labels and offers an overview on recent efforts in developing selective and sensitive reagents for the detection of metal ions in biological systems.

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Section: Design Strategies For Cation-responsive Fluorescent Indicmentioning

confidence: 99%

Metal-Ion-Responsive Fluorescent Probes for Two-Photon Excitation Microscopy

2010

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“…Processes related to two-photon absorption (2PA) have attracted attention in recent years owing to diverse applications in various fields, such as photodynamic therapy [1,2], optical-limiting [3][4][5], optical data storage [6,7], upconversion lasing [8,9], 3D microfabrication [10,11] and two-photon excited fluorescence microscopy [12,13]. 2PA occurs when molecules are exposed to intense laser pulses.…”

Section: Introductionmentioning

confidence: 99%

Two-photon absorption properties of a novel class of triarylamine compounds

Piovesan

Boni

Ishow

et al. 2010

Chemical Physics Letters

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a b s t r a c tTwo-photon absorption spectra of a triarylamine compounds dissolved in toluene were measured using the well-known Z-scan technique, employing 120-fs laser pulse-width. According to the results, an extra band located at around 900 nm was observed only for triarylamine with azoaromatic units. On the other hand, a shift in the two-photon absorption band for triarylamine, with and without azoaromatic units, is observed when different electron donor/acceptors groups are changed. The fitting of the spectra, using sum-over-states model, allowed us to obtain the spectroscopic parameters of each molecule, which appears to be in reasonable agreement with molecules presenting similar structural moieties.

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“…25 Herein, the focus has been to optimize the two-photon action cross section of fluorophores 6 and 11 in order to maximize the 2PFM imaging penetration within tumor tissue. 16 The optimal dye ( 10 ) was conjugated to the DC-101 antibody to facilitate observation of the formation of new vessels that overexpress VEGFR-2 receptor deep within the tumor.…”

Section: Resultsmentioning

confidence: 99%

“…The fluorophore design was based on a small series of efficient 2PA dyes that were recently reported. 16 The architecture of the fluorophores involved a fluorenyl core flanked by a triple bond- thiophene bridge (π) that led to an electron withdrawing group on one side (A). On the other, the fluorenyl core was tethered to the anti-VEGFR-2 that served as a donor (D).…”

Section: Introductionmentioning

confidence: 99%

Two-Photon Fluorescence Vascular Bioimaging with New Bioconjugate Probes Selective toward the Vascular Endothelial Growth Factor Receptor 2

Andrade¹,

Yanez²,

Ahn³

et al. 2011

Bioconjugate Chem.

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We report the synthesis and characterization of two amine reactive fluorescent dyes with efficient two-photon absorption (2PA) properties and high fluorescence quantum yields. Bioconjugation of these dyes with the DC-101 antibody proved to be useful for selectively imaging the vascular endothelial growth factor receptor 2 (VEGFR-2) in cells expressing this receptor in vitro and in “whole” mounted excised tumors (ex vivo) by two-photon fluorescence microscopy (2PFM). The penetration depths reached within the tumors by 2PFM was over 800 μm. In addition, the concentration of dye required for incubation of these bioconjugates was in the picomolar domain, the probes possessed very good photostability, and the 2PFM setup did not require any additional means of increasing the collection efficiencies of fluorescent photons to achieve the relatively deep tissue imaging that was realized, due, in large part, to the favorable photophysical properties of the new probes.

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A Series of Fluorene-Based Two-Photon Absorbing Molecules: Synthesis, Linear and Nonlinear Characterization, and Bioimaging

Cited by 69 publications

References 30 publications

Metal-Ion-Responsive Fluorescent Probes for Two-Photon Excitation Microscopy

Metal-Ion-Responsive Fluorescent Probes for Two-Photon Excitation Microscopy

Two-photon absorption properties of a novel class of triarylamine compounds

Two-Photon Fluorescence Vascular Bioimaging with New Bioconjugate Probes Selective toward the Vascular Endothelial Growth Factor Receptor 2

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