betadex and nile-red

An efficient artificial light-harvesting system is fabricated from a cyclic polysaccharide, sulfato-β-cyclodextrin (SCD); an aggregation-induced emission molecule, an oligo(phenylenevinylene) derivative (OPV-I); and a fluorescent dye, nile red (NiR), via noncovalent interactions in an aqueous solution. In this system, the OPV-I/SCD supramolecular assembly acts as a donor, and NiR that is loaded into the OPV-I/SCD assembly acts as an acceptor. Significantly, an efficient energy-transfer process occurs between the OPV-I/SCD assembly and the loaded NiR, leading to an extremely high antenna effect.

Topics: beta-Cyclodextrins; Biocompatible Materials; Fluorescence Resonance Energy Transfer; Fluorescent Dyes; Furans; Light; Oxazines; Polymers; Water

Interaction of cationic phenosafranin (PSF), anionic 8-anilino-1-naphthalene sulfonate (ANS) and non-ionic nile red (NR) have been studied with the zwitterionic phospholipid, egg yolk L-α-phosphatidylcholine (EYPC). The study reveals discernible binding interactions of the three fluorescent probes with the EYPC lipid vesicle. Once the binding of the probes with the lipid is established, the effect of cyclic oligosaccharide, β-cyclodextrin (β-CD), on these lipid bound probes has been investigated. Different fluorometric techniques suggest that addition of β-CD to the probe-lipid complexes leads to the release of the probes from the lipid medium through the formation of probe-β-CD inclusion complexes. A competitive binding of the probes between β-cyclodextrin and the lipid is ascribed to be responsible for the effect. This provides an easy avenue for the removal of the probe molecules from the lipid environment. Extension of this work with drug molecules in cell membranes is expected to give rise to a strategy for the removal of adsorbed drugs from the cell membranes by the use of non-toxic β-cyclodextrin.

Topics: Anilino Naphthalenesulfonates; Animals; beta-Cyclodextrins; Binding Sites; Binding, Competitive; Egg Yolk; Fluorescent Dyes; Fluorometry; Oxazines; Phenazines; Phosphatidylcholines

The function of membrane receptors in the nervous system depends on physicochemical characteristics of neuronal membranes such as membrane order and phase. In this work, we have monitored the changes in hippocampal membrane order and related parameters by cholesterol and protein content utilizing a Nile Red-based phase-sensitive fluorescent membrane probe NR12S. Since alteration of membrane cholesterol is often associated with membrane phase change, the phase-sensitive nature of NR12S fluorescence becomes useful in these experiments. Our results show that fluorescence spectroscopic parameters such as emission maximum, anisotropy, and lifetime of NR12S display characteristic dependence on membrane cholesterol content. Interestingly, cholesterol-dependent red edge excitation shift is displayed by NR12S under these conditions. Hippocampal membranes exhibited reduction in liquid-ordered phase upon cholesterol depletion. These results provide insight into changes in hippocampal membrane order in the overall context of cholesterol and protein modulation.

Topics: Animals; beta-Cyclodextrins; Cattle; Cell Membrane; Cholesterol; Fluorescent Dyes; Hippocampus; Oxazines; Spectrometry, Fluorescence

A class of new amphiphilic nanocapsules entangled with organometallic coordination polymers has been developed for the first time. Poly(2-(N,N-dimethyl amino)ethyl methacrylate)-b-polystyrene capped with β-cyclodextrin (β-CD) (CD-PDMAEMA-b-PS) is first synthesized using sequent RAFT polymerization of styrene and 2-(N,N-dimethyl amino)ethyl methacrylate with xanthate modified β-CD as chain transfer agent. The end group of β-CD is allowed to include 4,4'-bipyridine through host-guest inclusion to yield PDMAEMA-b-PS terminated with an inclusion complex of β-CD and bipyridine (bpy-PDMAEMA-b-PS), which is then used as surfactant to prepare emulsion droplets in toluene/water mixture. Upon addition of Ni(II), bipyridine coordinates with Ni(II) to form coordination polymers in the periphery of emulsion droplets, affording amphiphilic capsules entangled with organometallic coordination polymers, as confirmed by GPC, (1)H NMR, SEM, TEM, DLS, and so on. The organometallic coordination polymer capsules are capable of encapsulating organic cargoes. Interestingly, encapsulated cargoes can be extracted from the capsules without damaging the capsules. Such capsules are potential candidates for encapsulating and controlled release of organic cargoes.

Topics: beta-Cyclodextrins; Drug Delivery Systems; Magnetic Resonance Spectroscopy; Methacrylates; Microscopy, Electron, Scanning; Microscopy, Electron, Transmission; Molecular Weight; Nanocapsules; Nanotechnology; Nickel; Nylons; Organic Chemicals; Oxazines; Polymers; Polystyrenes; Pyridines; Surface-Active Agents

A successful endeavour has been made to develop a prospective strategy to oust the drug molecules adsorbed on the cell membranes by simply using the non-toxic β-cyclodextrin (β-CD). For this purpose, fluorescent probes of different geometries and charge characteristics, namely phenosafranin (PSF) and nile red (NR), were exploited for the in vitro studies using different lipids as model membranes. Considering the success of the in vitro study, the present work is extended to a live Chinese Hamster Ovary (CHO) cell using the dye NR acting as a model drug system. Steady state and time resolved confocal microscopic studies reveal that with the introduction of β-CD, some of the adsorbed dye molecules are dislodged from the CHO cell membrane to the nanocavity of β-CD resulting in the formation of dye-β-CD inclusion complex. This study promises the development of a prospective strategy for the removal of the adsorbed drugs from the cell membranes.

Topics: Adsorption; Animals; beta-Cyclodextrins; Cell Membrane; CHO Cells; Cricetinae; Cricetulus; Oxazines; Pharmacokinetics

Fluorometric measurements are exploited to explore the binding interactions of nile red (NR) with anionic lipid dimyristoyl-L-α-phosphatidylglycerol (DMPG), zwitterionic lipid dimyristoyl-L-α-phosphatidylcholine (DMPC) as well as neutral cyclic oligosaccharide β-cyclodextrin (β-CD) solutions. The binding constants are found to be quite high and comparable (within a factor of five). Series of spectral techniques like steady state fluorescence and fluorescence anisotropy study, micropolarity study, quenching study and time resolved experiments reveal that the addition of β-CD to the probe-lipid complexes results in weakening of the lipid-probe interaction and formation of probe-β-CD inclusion complexes leading to the removal of some of the probe (NR) molecules from the lipid environments. The extent of removal of NR is, however, more from DMPG than DMPC lipid. The phenomena are explained from the concept of competitive binding of the probe between the lipids and β-CD. Since lipids are the principal constituents of the cell walls, the work might make a foundation for the possible removal of excess of molecules like nile red adsorbed on the cell walls.

Topics: Adsorption; beta-Cyclodextrins; Binding, Competitive; Coloring Agents; Dimyristoylphosphatidylcholine; Fluorescence Polarization; Oxazines; Phosphatidylglycerols; Time Factors

Core-shell ZnO:MgO nanocrystals have been synthesized by a sequential preparative procedure and capped with carboxymethyl beta-cyclodextrin (CMCD) cavities, thereby rendering the surface of the nanocrystals hydrophilic and the particles water-soluble. The water-soluble CMCD-capped ZnO:MgO nanocrystals emit strongly in the visible region (450-680 nm) on excitation by UV radiation and are stable over extended periods and over a range of pH values. The integrity of the cyclodextrin cavities is preserved on capping and retains their capability for complexation of hydrophobic species in aqueous solutions. Here we report the use of the water-soluble cyclodextrin-capped ZnO:MgO nanocrystals as energy donors for fluorescence resonance energy transfer studies. The organic dye Nile Red has been included within the anchored cyclodextrin cavities to form a noncovalent CMCD ZnO:MgO-Nile Red assembly in aqueous solution. Significant Nile Red fluorescence at 640 nm is observed on band gap excitation of the ZnO:MgO in the UV, indicating efficient resonance energy transfer (RET) from the nanocrystals to the included dye. The number of acceptor molecules interacting with a single donor in the CMCD ZnO:MgO-Nile Red assembly may be altered by controlling the filling up of the anchored cavities by Nile Red, leading to a variation in the efficiency of resonance energy transfer. The donor-acceptor distance was estimated from the efficiency measurements. The Nile Red emission following RET shows a pronounced thermochromic shift, suggesting the possible use of the CMCD ZnO:MgO-Nile Red assembly as thermometers in aqueous solutions.

Topics: beta-Cyclodextrins; Crystallization; Fluorescence Resonance Energy Transfer; Macromolecular Substances; Magnesium Oxide; Materials Testing; Molecular Conformation; Nanostructures; Nanotechnology; Oxazines; Particle Size; Surface Properties; Water; Zinc Oxide

The fluorophore, Nile Red, effectively works as a polarity-sensitive fluorescence probe. We have designed a new nucleoside modified by Nile Red for examining the change in the polarity of the microenvironment surrounding DNA. We synthesized a Nile Red nucleoside (1), formed by replacing nucleobases with Nile Red, through the coupling of a 2-hydroxylated Nile Red derivative and 1,2-dideoxyglycan. This nucleoside showed a high solvatofluorochromicity. The fluorescence of 1 incorporated into DNA was greatly shifted to shorter wavelength by the addition of beta-cyclodextrin. The photophysical function of the Nile Red nucleoside will be a good optical indicator for monitoring the change in the micropolarity properties at a specific site on target sequences with interaction between DNA and DNA-binding molecules.

Topics: beta-Cyclodextrins; DNA; Fluorescent Dyes; Nucleosides; Oxazines; Spectrometry, Fluorescence