Bodipy-630

Fatty Acid Transporters. Figure 2 Quencher-based real-time fatty acid uptake assay with a fluorescently labeled FFA analogue (C1-Bodipy-C12). Predominantly protein-mediated fatty acid uptake by 3T3-L1 adipocytes (diamonds) was compared with diffusion-driven uptake by fibroblasts (squares) using the QBT Fatty Acid Uptake reagent (Molecular Devices Corp., CA, USA), which contains C1-Bodipy-C12 as substrate in conjunction with a cell impermeable quencher. Uptake kinetics was recorded using a Gemini fluorescence plate reader. Error bars indicate the standard deviations from 12 independent wells. RFU relative fluorescence units. 

Since our backbone 2 aPNA incorporates six Lys residues in its peptide sequence and is cationic at a physiological pH, we were optimistic that this aPNA would be taken up into cells without the need for any external carrier system. To answer the simple question of whether b2 aPNAs are intemahzed, a standard fluorescence microscopy experiment was performed to see if whole cells that were incubated with a fluorescent-labeled aPNA would internahze labeled material [70]. Chinese Hamster Ovary (CHO) cells in culture were incubated with BODIPY-la-beled TCCCT(b2) at 37 °C for various periods of time. Following incubation, the cells were rinsed in phosphate-buffered sahne (PBS), fixed with 4% formaldehyde at ambient temperature for 20 min, then washed with PBS and stored in a refrigerator until examined by fluorescence microscopy. 

Fig. 5.7 Fluorescence micrograph of CHO cells incubated with different concentrations of BODIPY-labeled aPNA at different times at 37°C...

Three types of reactive spectrally distinct fluorophores, namely lissamine rhoda-mine (LR) 80, 7-dimethylaminocoumarin (DMAC) 81, and bodipy-630 (BDPY) 82 dyes, prepared by coupling 3-azidopropylamine or propargylamine to commercially available amine-reactive dyes were evaluated for the use in selective dye-labeling of newly synthesised proteins in Rat-1 fibroblasts. 

Guminski Y, Grousseaud M, Cugnasse S et al (2009) Synthesis of conjugated spermine derivatives with 7-nitrobenzoxadiazole (NBD), rhodamine and bodipy as new fluorescent probes for the polyamine transport system. Bioorg Med Chem Lett 19 2474—2477... 

The number of new NIR fluorophores that can be used in biological systems has grown substantially in recent years as a consequence of extensive research efforts to improve the properties of available dyes. A brief overview of the various types of long-wavelength (above 600 nm) fluorophores including phycobiliproteins, BODIPY, and Alexa Fluor dyes (Life Technologies), Cy dyes (GE Healthcare),... 

BODIPY (4,4-dilluoro-4-bora-3a,4a-diaza-A-indaccnc) Dyes. 162... 

Fluorophores containing 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene as a core skeleton are commonly designated as BODIPY fluorophores. Due to their useful photophysical properties including high fluorescence quantum yields, high molar absorption coefficient, narrow absorption and emission band width, and their high photostability [50], BODIPY dyes are proven to be extremely versatile and useful in many biological applications Fig. 11 [68]. 

The first BODIPY fluorophore was synthesized by Treibs and Kreuzer in 1968 [69]. As described in recent review article [70], BODIPY dyes can be categorized into... 

Symmetrically substituted BODIPY dyes are relatively easy to be synthesized via the condensation of pyrroles with carbonyl electrophiles, such as acyl chlorides,... 

Fig. 12 Synthetic scheme for symmetrically substituted BODIPY dyes (a) and unsymmetrically substituted BODIPY dyes (b)...

On the other hand, the introduction of halide substituents at the C-2 and C-6 position decreases fluorescence quantum yields and gives a bathochromic shift of emission maxima. For example, bromine at the C-2 and C-6 position in compound 14b deteriorates fluorescence quantum yields from 0.95 (14a) to 0.45 and the emission maximum is red-shifted by 42 nm. Moreover, iodine at the C-2,6 position in compound 14d gives the similar bathochromic shift to bromine (14b, 44 nm) and more dramatic reduction in quantum yields (almost nonfluorescent, photophysical properties were interpreted as the heavy atom effect of halides on a BODIPY core skeleton. The bathochromic shift of BODIPY dyes without dramatic decrease in quantum yield was observed by the introduction of vinyl substituents at the C-2 and C-6 position. The extension of conjugation... 

Fig. 13 Structure-photophysical property relationship at the C-l and C-7 position of BODIPY derivatives...

The C-3 and C-5 position of BODIPY core skeleton is one of the most important points for the substitution to tune photophysical properties, including absorption and/or emission maxima as well as fluorescence quantum yields. First of all, the introduction of amine-based (15d-15g) or sulfur-based (15b-15c) nucleophiles can... 

Compared to the introduction of various substituents at the BODIPY core skeleton, the extension of conjugation length can be achieved by the fusion of aryl group via furan or (hetero)carbocycles. As shown in Fig. 16, the furan-based... 

Fig. 16 Structural transformation through the introduction of aryl moiety at the C-8 position or through the extension of conjugation length via fused heteroaryl moiety on BODIPY core skeletons...

Fig. 17 Synthetic schemes of BODIPY-based combinatorial library and 3D scatter plot of synthesized library members according to excitation wavelength, emission maxima, and brightness (fa x ). All the photophysical properties were measured in MeOH...

Loudet A, Burgess K (2007) BODIPY dyes and their derivatives syntheses and spectroscopic properties. Chem Rev 107 4891 1932... 

Lee JS, Kang NY, Kim YK, Samanta A, Feng S, Kim HK, Vendrell M, Park JH, Chang YT (2009) Synthesis of a BODIPY library and its application to the development of live cell glucagon imaging probe. J Am Chem Soc 131 10077-10082... 

There are a lot of probes with charge transfer, among which are Prodan, Laurdan, and derivatives, derivatives of stilbene, and Bodipy. For some of them,... 

BODIPY is a short for 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene, the basic structure of this type of fluorophore (see Fig. 6.5). Derivatives of this dye have been created by modification of positions 1, 3, 5, 7, and 8, generating an array of fluorophores with very distinct excitation and emission properties [38]. Molecular Probes has synthesized a wide number of BODIPY dyes whose excitation... 

Fig. 6.5. BODIPY and some derivatives. BODIPY = 4,4-difluoro-4bora-3a,...

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