Evolution of Fluorescein as a Platform for Finely Tunable Fluorescence Probes

Urano, Yasuteru; Kamiya, Mako; Kanda, Kojiro; Ueno, Takahiro; Hirose, Keikichi; Nagano, Tetsuo

doi:10.1021/ja043919h

Cited by 647 publications

(650 citation statements)

References 28 publications

(42 reference statements)

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“…Increased steric hindrance at the central carbon will inhibit the formation of the solvent adduct. Furthermore, rotation of the phenyl ring, leading to the relaxation of excited states, will be greatly suppressed (10).…”

Section: Resultsmentioning

confidence: 99%

Seminaphthofluorones are a family of water-soluble, low molecular weight, NIR-emitting fluorophores

Yang

Lowry

et al. 2008

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

115

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A readily accessible new class of near infrared (NIR) molecular probes has been synthesized and evaluated. Specific fluorophores in this unique xanthene based regioisomeric seminaphthofluorone dye series exhibit a combination of desirable characteristics including (i) low molecular weight (339 amu), (ii) aqueous solubility, and (iii) dual excitation and emission from their fluorescent neutral and anionic forms. Importantly, systematic changes in the regiochemistry of benzannulation and the ionizable moieties afford (iv) tunable deep-red to NIR emission from anionic species and (v) enhanced Stokes shifts. Anionic SNAFR-6, exhibiting an unusually large Stokes shift of Ϸ200 nm (5,014 cm ؊1 ) in aqueous buffer, embodies an unprecedented fluorophore that emits NIR fluorescence when excited in the blue/green wavelength region. The successful use of SNAFR-6 in cellular imaging studies demonstrates proof-of-concept that this class of dyes possesses photophysical characteristics that allow their use in practical applications. Notably, each of the new fluorophores described is a minimal template structure for evaluation of their basic spectral properties, which may be further functionalized and optimized yielding concomitant improvements in their photophysical properties.NIR dyes ͉ xanthenes D yes active in the near infrared (NIR) region (Ͼ700 nm) have been under development since the first discovery of dyes with such spectral properties in the early twentieth century. NIR dyes have found wide applicability in optical recording, thermal writing displays, laser printers, laser filters, infrared photography, photodynamic therapy, and numerous other applications (1). More recently, NIR dyes have attracted considerable attention for biological and biomedical applications (2) because of inherent advantages, such as minimal interfering absorption and fluorescence from biological samples, inexpensive laser diode excitation, reduced scattering, and enhanced tissue penetration depth. Surprisingly, only a relatively few classes of NIR dyes, such as the phthalocyanines, cyanines, and squaraines, are available for use in these fields. Each of these classes of dyes has its own distinct advantages and disadvantages; moreover, common limitations include relatively small Stokes shifts and incompatibility with common f luorophores for multiplexing applications. Clearly, there is a strong need and interest in enriching the available pool of NIR fluorophores.Annulation has proven to be quite successful for effecting bathochromic shifts through extension of the conjugated system of various dye architectures (3-4). Lee et al. (3) first synthesized the red-shifted type [c] naphthofluorescein framework nearly two decades ago. In addition, seminaphthofluorescein (SNAFL) and seminaphthorhodafluor (SNARF) with type [c] annulations, as developed by Haugland and coworkers (4), are in wide use today. These dyes primarily display red-shifted emissions that have maxima in the red spectral region. Importantly, although the use of type [c] annulation ha...

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Section: Resultsmentioning

confidence: 99%

Seminaphthofluorones are a family of water-soluble, low molecular weight, NIR-emitting fluorophores

Yang

Lowry

et al. 2008

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

115

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“…26 All the values including that of 1 Me , 2 Me , 3 Me can be fitted with the Marcus equation. It can be seen that 3 Me lies between the fluorescence off/on thresholds of the anionic and neutral forms, indicating that it is the most suitable scaffold fluorophore for developing a highly sensitive fluorescence probe with enhanced cellular retention.…”

Section: Relationship Between Oxidation Potential and Fluorescence Qumentioning

confidence: 99%

“…[23][24][25] In our previous work, we focused on simple, rapid, and sensitive detection of β-galactosidase activity, and developed a highly sensitive fluorescence probe for β-galactosidase, TG-βGal (Scheme 1a). 26 This probe was rationally designed to show a dramatic fluorescence activation (up to 440-fold) upon reaction with β-galactosidase, and was successfully used to visualize β-galactosidase activity in living cells. We considered that such probes might be suitable to visualize tumors in vivo.…”

Section: Introductionmentioning

confidence: 99%

An Enzymatically Activated Fluorescence Probe for Targeted Tumor Imaging

et al. 2007

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Abstractβ-Galactosidase is a widely used reporter enzyme, but although several substrates are available for in vitro detection, its application for in vivo optical imaging remains a challenge. To obtain a probe suitable for in vivo use, we modified our previously developed activatable fluorescence probe, TGβGal (J. Am. Chem. Soc., 2005, 127, 4888-4894), on the basis of photochemical and photophysical experiments. The new probe, AM-TG-βGal, provides a dramatic fluorescence enhancement upon reaction with β-galactosidase, and further hydrolysis of the ester moiety by ubiquitous intracellular esterases affords a hydrophilic product that is well retained within the cells without loss of fluorescence. We used a mouse tumor model to assess the practical utility of AM-TG-βGal, after confirming that tumors in the model could be labeled with avidin-β-galactosidase conjugate. This conjugate was administered to the mice in vivo, followed by AM-TG-βGal, and subsequent ex vivo fluorescence imaging clearly visualized intraperitoneal tumors as small as 200 μm. This strategy has potential clinical application, for example in video-assisted laparoscopic tumor resection.

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“…PET19 can be used to modulated the generation of 1 O 2 when compete with others mechanisms, especially ISC. It is well known that 1 O 2 quantum yield is directly related to the efficiency of ISC (generally, high ISC efficiency results in high 1 O 2 quantum yield).…”

Section: Pet Regulation Mechanismmentioning

confidence: 99%

Controllable Photodynamic Therapy Implemented by Regulating Singlet Oxygen Efficiency

et al. 2017

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With singlet oxygen (1O2) as the active agent, photodynamic therapy (PDT) is a promising technique for the treatment of various tumors and cancers. But it is hampered by the poor selectivity of most traditional photosensitizers (PS). In this review, we present a summary of controllable PDT implemented by regulating singlet oxygen efficiency. Herein, various controllable PDT strategies based on different initiating conditions (such as pH, light, H2O2 and so on) have been summarized and introduced. More importantly, the action mechanisms of controllable PDT strategies, such as photoinduced electron transfer (PET), fluorescence resonance energy transfer (FRET), intramolecular charge transfer (ICT) and some physical/chemical means (e.g. captivity and release), are described as a key point in the article. This review provide a general overview of designing novel PS or strategies for effective and controllable PDT.

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Evolution of Fluorescein as a Platform for Finely Tunable Fluorescence Probes

Cited by 647 publications

References 28 publications

Seminaphthofluorones are a family of water-soluble, low molecular weight, NIR-emitting fluorophores

Seminaphthofluorones are a family of water-soluble, low molecular weight, NIR-emitting fluorophores

An Enzymatically Activated Fluorescence Probe for Targeted Tumor Imaging

Controllable Photodynamic Therapy Implemented by Regulating Singlet Oxygen Efficiency

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