Comparative Photostability Studies of BODIPY and Fluorescein Dyes by Using Fluorescence Correlation Spectroscopy

Hinkeldey, Babette; Schmitt, Alexander; Jung, Gregor

doi:10.1002/cphc.200800299

Cited by 98 publications

(107 citation statements)

References 67 publications

Supporting

Mentioning

103

Contrasting

Unclassified

Order By: Relevance

“…Additionally, these fluorophores are much more photostable in the presence of oxygen than, for example, rhodamine or cyanine derivatives, which is also likely related to their redox properties: Because of their high oxidation potential they are not efficiently oxidized by molecular oxygen, which is considered to be a key step in photobleaching pathways (41). Recalling that living cells themselves provide redox active agents such as the reductants glutathione and ascorbic acid as well as oxidants such as quinone derivatives and oxygen, superresolution under in vivo conditions may become possible on the basis of the switchable molecules presented.…”

Section: [1]mentioning

confidence: 99%

Controlling the fluorescence of ordinary oxazine dyes for single-molecule switching and superresolution microscopy

Vogelsang

Cordes

Forthmann

et al. 2009

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

257

331

View full text Add to dashboard Cite

Fluorescent molecular switches have widespread potential for use as sensors, material applications in electro-optical data storages and displays, and superresolution fluorescence microscopy. We demonstrate that adjustment of fluorophore properties and environmental conditions allows the use of ordinary fluorescent dyes as efficient single-molecule switches that report sensitively on their local redox condition. Adding or removing reductant or oxidant, switches the fluorescence of oxazine dyes between stable fluorescent and nonfluorescent states. At low oxygen concentrations, the off-state that we ascribe to a radical anion is thermally stable with a lifetime in the minutes range. The molecular switches show a remarkable reliability with intriguing fatigue resistance at the single-molecule level: Depending on the switching rate, between 400 and 3,000 switching cycles are observed before irreversible photodestruction occurs. A detailed picture of the underlying photoinduced and redox reactions is elaborated. In the presence of both reductant and oxidant, continuous switching is manifested by ''blinking'' with independently controllable on-and off-state lifetimes in both deoxygenated and oxygenated environments. This ''continuous switching mode'' is advantageously used for imaging actin filament and actin filament bundles in fixed cells with subdiffraction-limited resolution.electron transfer ͉ molecular switch ͉ sensor ͉ single-molecule spectroscopy M olecular switches are single-molecule devices, and hence they are key building-blocks for future, bottom-up nanotechnological devices in computers, data storages, (bio-) sensors, and displays. Furthermore, they are exciting molecules for triggered drug-release or for superresolution imaging (1-3). Molecular switches possess at least 2 stable states and can be converted between these states by external stimuli. These external stimuli can essentially be any kind of physical or chemical trigger, such as light, electricity, or certain chemical reactions. Fluorescence is a preferred transduction mechanism because of its ease of noninvasive detection with ultimate sensitivity (i.e., single-molecule sensitivity). For future devices and for superresolution microscopy, it is also important that the molecular switches can be operated at the level of single molecules. This requirement imposes further demands with respect to reliability, reproducibility, response time, and fatigue resistance. Although the single-molecule approach provides detailed information about the properties and mechanisms, only a few examples of fluorescent switches have been demonstrated (4, 5). Among the fluorescent switches, there are systems that use 2 different wavelengths for switching (photoswitchable molecules) (6-13), those that switch the efficiency of photoinduced electron transfer (14, 15) and those that respond to pH changes (15,16).Here, we show that based on a detailed understanding of their photophysics, ordinary, fluorescent dyes can act as single-molecule switches and sensors. By adapting...

show abstract

Section: [1]mentioning

confidence: 99%

Controlling the fluorescence of ordinary oxazine dyes for single-molecule switching and superresolution microscopy

Vogelsang

Cordes

Forthmann

et al. 2009

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

257

331

View full text Add to dashboard Cite

show abstract

“…Some limitations to fluorescence-based tags include that they are light-sensitive, and special care must be taken to avoid light during preparation and processing [86, 87]. It is also necessary to utilize specialized detection systems such as fluorescence gel-based imagers and fluorescence microscopes [56, 78].…”

Section: An Overview Of Tagsmentioning

confidence: 99%

Detection of electrophile-sensitive proteins

Wall

Smith

Ricart

et al. 2014

Biochimica et Biophysica Acta (BBA) - General Subjects

View full text Add to dashboard Cite

Background Redox signaling is an important emerging mechanism of cellular function. Dysfunctional redox signaling is increasingly implicated in numerous pathologies, including atherosclerosis, diabetes, and cancer. The molecular messengers in this type of signaling are reactive species which can mediate the post-translational modification of specific groups of proteins, thereby effecting functional changes in the modified proteins. Electrophilic compounds comprise one class of reactive species which can participate in redox signaling. Electrophiles modulate cell function via formation of covalent adducts with proteins, particularly cysteine residues. Scope of Review This review will discuss the commonly used methods of detection for electrophile-sensitive proteins, and will highlight the importance of identifying these proteins for studying redox signaling and developing novel therapeutics. Major Conclusions There are several methods which can be used to detect electrophile-sensitive proteins. These include the use of tagged model electrophiles, as well as derivatization of endogenous electrophile-protein adducts. General Significance In order to understand the mechanisms by which electrophiles mediate redox signaling, it is necessary to identify electrophile-sensitive proteins and quantitatively assess adduct formation. Strengths and limitations of these methods will be discussed.

show abstract

“…Although previous fluorescent-Pt compounds have been described elsewhere [15-17] , they use fluorescein derivatives, which are generally not ideal for intravital imaging due to photobleaching and poor fluorescence in intracellular environments [18] . In contrast, BODIPY-FL (BFL) has been shown to exhibit excellent properties for in vivo imaging [19] , including environmentally robust fluorescence; structural stability in vivo; high photostability; high brightness; and favorable cell permeability [20-22] . Therefore, here we developed four new BFL-conjugated Pt compounds and demonstrated their applicability to high-resolution intravital imaging of PK/PD in a xenograft model of cancer.…”

mentioning

confidence: 99%

Platinum Compounds for High‐Resolution In Vivo Cancer Imaging

et al. 2014

View full text Add to dashboard Cite

Platinum(II) compounds, principally cisplatin and carboplatin, are commonly used front-line cancer therapeutics. Despite widespread use and the interest of developing new derivatives, including nanoformulations with improved properties, it has been difficult to visualize Pt compounds in live subjects, in real-time, and with subcellular resolution. Here we present four novel cisplatin- and carboplatin-derived fluorescent imaging compounds for quantitative intravital cancer imaging. We conjugate boron dipyromethene FL (BODIPY-FL) to PtII complexes for robust in vivo fluorescence, and show retained DNA-damaging and cytotoxic properties. We image pharmacokinetics and tumor uptake in a xenograft cancer mouse model. Finally, we present a genetic reporter of single-cell DNA damage for in vivo imaging, and simultaneously monitor Pt drug accumulation and resultant DNA damage in individual tumor cells, at subcellular resolution, and in real-time in a live animal model of cancer.

show abstract

Comparative Photostability Studies of BODIPY and Fluorescein Dyes by Using Fluorescence Correlation Spectroscopy

Cited by 98 publications

References 67 publications

Controlling the fluorescence of ordinary oxazine dyes for single-molecule switching and superresolution microscopy

Controlling the fluorescence of ordinary oxazine dyes for single-molecule switching and superresolution microscopy

Detection of electrophile-sensitive proteins

Platinum Compounds for High‐Resolution In Vivo Cancer Imaging

Contact Info

Product

Resources

About