A synthesis and properties of new 4,4-difluoro-3a,4a-diaza-s-indacene (BODIPY)-labeled lipids

Болдырев, Иван; Molotkovsky, Jul.G.

doi:10.1134/s1068162006010080

Cited by 27 publications

(31 citation statements)

References 13 publications

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“…Briefly, 30 μL exosomes with a concentration of 4×10 11 particles/mL were mixed with 20 μL BODIPY-PC (0.03 mg/ml) (31) and supplemented with 70 μL deionized water; the mixture was incubated for 45 min at 37°C in the dark. Unbound label was removed using a Zeba TM column (Life Technologies).…”

Section: Methodsmentioning

confidence: 99%

Development of exosome-encapsulated paclitaxel to overcome MDR in cancer cells

Kim

Haney

Zhao

et al. 2016

Nanomedicine: Nanotechnology, Biology and Medicine

1,102

881

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Exosomes have recently come into focus as “natural nanoparticles” for use as drug delivery vehicles. Our objective was to assess the feasibility of an exosome-based drug delivery platform for a potent chemotherapeutic agent, paclitaxel (PTX), to treat MDR cancer. Herein, we developed and compared different methods of loading exosomes released by macrophages with PTX (exoPTX), and characterized their size, stability, drug release, and in vitro antitumor efficacy. Reformation of the exosomal membrane upon sonication resulted in high loading efficiency and sustained drug release. Importantly, incorporation of PTX into exosomes increased cytotoxicity more than 50 times in drug resistant MDCKMDR1 (Pgp+) cells. Next, our studies demonstrated a nearly complete co-localization of airway-delivered exosomes with cancer cells in a model of murine Lewis Lung Carcinoma pulmonary metastases, and a potent anticancer effect in this mouse model. We conclude that exoPTX holds significant potential for the delivery of various chemotherapeutics to treat drug resistant cancers.

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Section: Methodsmentioning

confidence: 99%

Development of exosome-encapsulated paclitaxel to overcome MDR in cancer cells

Kim

Haney

Zhao

et al. 2016

Nanomedicine: Nanotechnology, Biology and Medicine

1,102

881

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“…Me 4 -BODIPY-8 probe synthesis Figure 1 summarizes the syntheses of the Me 4 -BODIPY-8-labeled fatty acids (XIII-XVI) and their insertion into complex lipids (XVII-XX), which have been described in detail previously (20). Briefly, for the preparation of acids XIII-XVI, the route of Burghart et al (44) was followed, with minor modifications.…”

Section: Resultsmentioning

confidence: 99%

“…Other phosphatidylcholines were from Avanti Polar Lipids (Alabaster, AL). The syntheses of the Me 4 -BODIPY-8-labeled probes (20) are summarized in the scheme (Fig. 1).…”

Section: Methodsmentioning

confidence: 99%

New BODIPY lipid probes for fluorescence studies of membranes

Болдырев

Zhai

Momsen

et al. 2007

Journal of Lipid Research

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Many fluorescent lipid probes tend to loop back to the membrane interface when attached to a lipid acyl chain rather than embedding deeply into the bilayer. To achieve maximum embedding of BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) fluorophore into the bilayer apolar region, a series of sn-2 acyl-labeled phosphatidylcholines was synthesized bearing 4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene-8-yl (Me 4 -BODIPY-8) at the end of C 3 -, C 5 -, C 7 -, or C 9 -acyl. A strategy was used of symmetrically dispersing the methyl groups at BODIPY ring positions 1, 3, 5, and 7 to decrease fluorophore polarity. Iodide quenching of the phosphatidylcholine probes in bilayer vesicles confirmed that the Me 4 -BODIPY-8 fluorophore was embedded in the bilayer. Parallax analysis of Me 4 -BODIPY-8 fluorescence quenching by phosphatidylcholines containing iodide at different positions along the sn-2 acyl chain indicated that the penetration depth of Me 4 -BODIPY-8 into the bilayer was determined by the length of the linking acyl chain. Evaluation using monolayers showed minimal perturbation of ,10 mol% probe in fluid-phase and cholesterol-enriched phosphatidylcholine. Spectral characterization in monolayers and bilayers confirmed the retention of many features of other BODIPY derivatives (i.e., absorption and emission wavelength maxima near 498 nm and ?506-515 nm) but also showed the absence of the 620-630 nm peak associated with BODIPY dimer fluorescence and the presence of a 570 nm emission shoulder at high Me 4 -BODIPY-8 surface concentrations. We conclude that the new probes should have versatile utility in membrane studies, especially when precise location of the reporter group is needed. Fluorescent lipid probes have proven to be valuable tools in membrane studies (see Ref. 1 for review). Because the determination of depth-dependent parameters of bilayers can benefit the understanding of membranous structures (2), sets of probes bearing the same fluorophore at different distances from the bilayer surface are potentially quite useful. Ideally, such fluorophores should be apolar enough to localize at the membrane depth that reflects the apolar nature of the surrounding acyl chain region without being strongly influenced by the transbilayer polarity gradient (3). The first probe set designed to achieve this goal was a series of n-(9-anthroyloxy) fatty acids synthesized by Thulborn and Sawyer (4), who showed that the fluorophore resided in the bilayer at a graded series of depths that coincided with the attachment point of the anthroyloxy fluorophore along the acyl chain. Other widely used fluorophores, such as N-dansyl (5) or N-NBD (6, 7), have been shown to have polar characteristics that interfere with localization deep inside the bilayer even when attached to the end of the acyl chain.During the past decade, BODIPY (4,4-difluoro-4-bora3a,4a-diaza-s-indacene) fluorophore probes have found a wide range of applications in cell biology and biophysics, even though this zwitterionic fluorophore wa...

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“…The formation of strong covalent bond in these complexes determines the strong polarization of the ligand's π electron system, resulting in the formation of clearly pronounced chro mophoric and fluorescent properties for compounds whose modification involves both internal (the nature of substituents in pyrrol rings of the ligand and the addition of various substituents to the boron atom) and external factors (the solvate and polymer shells in solutions and various materials). This offers great pos sibilities for using Bodipy as components of optical systems, agents for photodynamic therapy of oncolog ical diseases, and high intensity chromophoric and fluorescent markers and sensors in analytical chemis try, as was demonstrated by the data from [3][4][5].…”

Section: Introductionmentioning

confidence: 99%

Relationship between the spectral properties of solutions of borofluoride complex of alkylated dipyrromethene and the physicochemical parameters of solvents

Marfin

Rumyantsev

Fadeev

et al. 2012

Russ. J. Phys. Chem.

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Spectral and photophysical characteristics of borofluoride complex of alkylated dipyrromethene (Bodipy) are determined by means of absorption and fluorescence electron spectroscopy in various organic solvents. Dependences of the spectral and photophysical characteristics of Bodipy solutions vs. the physico chemical parameters of solvents are obtained by linear regression analysis and the contribution from each parameter to the property under study is determined. It is established that the negative solvatochromic effect is intrinsic for Bodipy. It is concluded that specific interactions contribute substantially to the properties of the chromophore, which are determined by the electron donor properties of the solvent.Keywords: electron spectroscopy, fluorescence, organic solvents borofluoride complex of alkylated dipyr romethene.Note: λ abs and λ fl values were obtained for Bodipy solutions with concentrations of 1 × 10 -5 and 1 × 10 -6 mol/L, respectively.

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A synthesis and properties of new 4,4-difluoro-3a,4a-diaza-s-indacene (BODIPY)-labeled lipids

Cited by 27 publications

References 13 publications

Development of exosome-encapsulated paclitaxel to overcome MDR in cancer cells

Development of exosome-encapsulated paclitaxel to overcome MDR in cancer cells

New BODIPY lipid probes for fluorescence studies of membranes

Relationship between the spectral properties of solutions of borofluoride complex of alkylated dipyrromethene and the physicochemical parameters of solvents

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