Improved Photostability and Fluorescence Properties through Polyfluorination of a Cyanine Dye

Renikuntla, Babu Rao; Rose, Heather; Eldo, Joby; Waggoner, Alan S.; Armitage, Bruce A.

doi:10.1021/ol036081w

Cited by 139 publications

(131 citation statements)

References 16 publications

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“…Traditional cyanine dyes display poor photostability, self-aggregation, and low quantum-yield solution. 37 Previous studies showed that both the excitation and emission wavelengths of these compounds were increased by the extension of the polymethyl chain. Most cyanine dyes are prone to self-aggregation, which is affected by the length of the carbon chain.…”

Section: Physical and Chemical Characteristics Of Near-infrared Fluormentioning

confidence: 99%

Review on near-infrared heptamethine cyanine dyes as theranostic agents for tumor imaging, targeting, and photodynamic therapy

2016

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Review on near-infrared heptamethine cyanine dyes as theranostic agents for tumor imaging, targeting, and photodynamic therapy," J. Biomed. Opt. 21(5), 050901 (2016), doi: 10.1117/1.JBO.21.5.050901. Abstract. A class of near-infrared fluorescence (NIRF) heptamethine cyanine dyes that are taken up and accumulated specifically in cancer cells without chemical conjugation have recently emerged as promising tools for tumor imaging and targeting. In addition to their fluorescence and nuclear imagingbased tumor-imaging properties, these dyes can be developed as drug carriers to safely deliver chemotherapy drugs to tumors. They can also be used as effective agents for photodynamic therapy with remarkable tumoricidal activity via photodependent cytotoxic activity. The preferential uptake of dyes into cancer but not normal cells is co-operatively mediated by the prevailing activation of a group of organic aniontransporting polypeptides on cancer cell membranes, as well as tumor hypoxia and increased mitochondrial membrane potential in cancer cells. Such mechanistic explorations have greatly advanced the current application and future development of NIRF dyes and their derivatives as anticancer theranostic agents. This review summarizes current knowledge and emerging advances in NIRF dyes, including molecular characterization, photophysical properties, multimodal development and uptake mechanisms, and their growing potential for preclinical and clinical use.

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Section: Physical and Chemical Characteristics Of Near-infrared Fluormentioning

confidence: 99%

Review on near-infrared heptamethine cyanine dyes as theranostic agents for tumor imaging, targeting, and photodynamic therapy

2016

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“…This tuning permits one to choose dyes for optimal sensitivity in relation to the linear or nonlinear excitation sources appropriate to the experimental system as well as minimization of spectral overlap with other fluorescent sensors or optical manipulations. Furthermore, fluorination is known to enhance the photostability of dye chromophores (32,33). For measurements that may be limited by low-dye copy numbers in small volumes and/or the need to record rapid transients, better photostability permits the collection of more photons per VSD molecule, thus improving the signal to noise ratio (S:N) of the optically recorded voltage activity.…”

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confidence: 99%

Palette of fluorinated voltage-sensitive hemicyanine dyes

Yan

Acker²,

Zhou

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

157

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Optical recording of membrane potential permits spatially resolved measurement of electrical activity in subcellular regions of single cells, which would be inaccessible to electrodes, and imaging of spatiotemporal patterns of action potential propagation in excitable tissues, such as the brain or heart. However, the available voltage-sensitive dyes (VSDs) are not always spectrally compatible with newly available optical technologies for sensing or manipulating the physiological state of a system. Here, we describe a series of 19 fluorinated VSDs based on the hemicyanine class of chromophores. Strategic placement of the fluorine atoms on the chromophores can result in either blue or red shifts in the absorbance and emission spectra. The range of one-photon excitation wavelengths afforded by these new VSDs spans 440-670 nm; the twophoton excitation range is 900-1,340 nm. The emission of each VSD is shifted by at least 100 nm to the red of its one-photon excitation spectrum. The set of VSDs, thus, affords an extended toolkit for optical recording to match a broad range of experimental requirements. We show the sensitivity to voltage and the photostability of the new VSDs in a series of experimental preparations ranging in scale from single dendritic spines to whole heart. Among the advances shown in these applications are simultaneous recording of voltage and calcium in single dendritic spines and optical electrophysiology recordings using two-photon excitation above 1,100 nm.fluorescence | microscopy O ptical recording techniques provide powerful tools for neurobiologists (1) and cardiac physiologists (2) to study detailed patterns of electrical activity over time and space in cells, tissues, and organs. Rational design methods, based on molecular orbital calculations of the dye chromophores and characterization of their binding and orientations in membranes (3-5), were used to engineer dye structures. The general class of dye chromophores called hemicyanine (also referred to as styryl dyes) has emerged from this effort as a good foundation for voltage-sensitive dyes (VSDs), because they exhibit electrochromism. This mechanism, also referred to as the molecular Stark effect, involves the differential interaction of the electric field in the membrane with the ground and excited states of the dye chromophore. Several important hemicyanine dyes were produced over the years, including di-4-ANEPPS (6, 7), di-8-ANEPPS (8), di-2-ANEPEQ (also known as JPW-1114) (9, 10), RH-421 and RH-795 (11), ANNINE-6 and ANNINE-6+ (12, 13), di-3-ANEPPDHQ (14, 15), di-4-ANBDQBS, and di-4-ANBDQPQ (16,17). Because the electrochromic mechanism is a direct interaction of the electric field with the chromophore and does not require any movement of the dye molecule, all of these dyes provide rapid absorbance and fluorescence responses to membrane potential (V m ); they are, therefore, capable of recording action potentials (APs). Other mechanisms can give more sensitive voltage responses in specialized applications (18)(19)(20)(21)(22). Addit...

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“…According to previous reports, 22 although the intersystem crossing yields for cyanine dyes are quite low, the cyanine dyes react rapidly with singlet oxygen. A myriad of factors such as lifetime at excited state, substituents, aggregation, air, water, solvent, and substrate have an effect on photofading by oxidative routes.…”

mentioning

confidence: 73%

Synthesis of Novel Hemicyanine Dyes for Color Compensating Film in Plasma Display Panels

Kim¹,

Park²,

Lee³

et al. 2014

Bulletin of the Korean Chemical Society

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Five novel cyanine dyes containing julolidine and indole moieties were synthesized. Several color compensating films for plasma display panels (PDP) were prepared using these dyes. The spectroscopic and physicochemical properties of the synthesized dyes in both solution and film state were evaluated. For each color compensating film, the optimum ratio of dye to binder was determined on the basis of transmittance, half band width, and photo-stability of the color compensating film. The five synthesized dyes showed sharp absorption peaks near 590 nm (orange light) and had molar extinction coefficients above 1 × 10. The melting point of the dyes was above 200 o C and photo-stability of the color compensating films was improved by introducing substituents at the 5th position on the indole derivatives.

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Improved Photostability and Fluorescence Properties through Polyfluorination of a Cyanine Dye

Cited by 139 publications

References 16 publications

Review on near-infrared heptamethine cyanine dyes as theranostic agents for tumor imaging, targeting, and photodynamic therapy

Review on near-infrared heptamethine cyanine dyes as theranostic agents for tumor imaging, targeting, and photodynamic therapy

Palette of fluorinated voltage-sensitive hemicyanine dyes

Synthesis of Novel Hemicyanine Dyes for Color Compensating Film in Plasma Display Panels

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