- Highly Efficient Encapsulation and Phase Separation of Apolar Molecules by Magnetic Shell-by-Shell-Coated Nanocarriers in Water
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We report on the development of a supramolecular nanocarrier concept that allows for the encapsulation and separation of small apolar molecules from water. The nanocarriers consist of shell-by-shell-coated nanoparticles such as TiO2 and ferromagnetic Fe3O4. The first ligand shell is provided by covalently bound hexadecyl phosphonic acid (PAC16) and the second shell by noncovalently assembled amphiphiles rendering the hybrid architecture soluble in water. Agitation of these constructs with water containing the hydrocarbons G1–G4, the fluorescent marker G5, the polychlorinated biphenyl PCB 77, or crude oil leads to a very efficient uptake (up to 411 %) of the apolar contaminant. In case of the hybrids containing a Fe3O4 core, straightforward phase separation by the action of an external magnet is provided. The load can easily be released by a final treatment with an organic solvent.
- Luchs, Tobias,Sarcletti, Marco,Zeininger, Lukas,Portilla, Luis,Fischer, Christian,Harder, Sjoerd,Halik, Marcus,Hirsch, Andreas
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- Smart Shell-by-Shell Nanoparticles with Tunable Perylene Fluorescence in the Organic Interlayer
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A new series of shell-by-shell (SbS)-functionalized Al2O3 nanoparticles (NPs) containing a perylene core in the organic interlayer as a fluorescence marker is introduced. Initially, the NPs were functionalized with both, a fluorescent perylene phosphonic acid derivative, together with the lipophilic hexadecylphosphonic acid or the fluorophilic (1 H,1 H,2 H,2H-perfluorodecyl)phosphonic acid. The lipophilic first-shell functionalized NPs were further implemented with amphiphiles built of aliphatic chains and polar head-groups. However, the fluorophilic NPs were combined with amphiphiles consisting of fluorocarbon tails and polar head-groups. Depending on the nature of the combined phosphonic acids and the amphiphiles, tuning of the perylene fluorescence can be accomplished due variations of supramolecular organization with the shell interface. Because the SbS-functionalized NPs dispose excellent dispersibility in water and in biological media, two sorts of NPs with different surface properties were tested with respect to biological fluorescent imaging applications. Depending on the agglomeration of the NPs, the cellular uptake differs. The uptake of larger agglomerates is facilitated by endocytosis, whereas individualized NPs cross directly the cellular membrane. Also, the larger agglomerates were preferentially incorporated by all tested cells.
- Stiegler, Lisa M. S.,Klein, Stefanie,Kryschi, Carola,Neuhuber, Winfried,Hirsch, Andreas
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- Manufacturing Nanoparticles with Orthogonally Adjustable Dispersibility in Hydrocarbons, Fluorocarbons, and Water
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We describe a universal wet-chemical shell-by-shell coating procedure resulting in colloidal titanium dioxide (TiO2) and iron oxide (Fe3O4) nanoparticles with dynamically and reversibly tunable surface energies. A strong c
- Zeininger, Lukas,Stiegler, Lisa M. S.,Portilla, Luis,Halik, Marcus,Hirsch, Andreas
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- CONJUGATE-BASED ANTIFUNGAL AND ANTIBACTERIAL PRODRUGS
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The invention provides conjugate-based antifungal or antibacterial prodrugs formed by coupling at least one anti-fungal agent or antibacterial agent with at least one linker and/or carrier. The prodrugs are of formula: (i) (AFA)m-X-(L)n; (ii) [(AFA)m′-X]p-L; (iii) AFA-[X-(L)n′]q; or (iv) (AFA)m″-X, wherein: AFA is an antifungal agent or an antibacterial agent; L is a carrier; X is a linker; m ranges from 1 to 10; n ranges from 2 to 10; m′ is 1 to 10; p is 1 to 10; n′ is 1 to 10; and q is 1 to 10, provided that q′ and n are not both 1; and m″ is 1 to 10. The invention also provides nanoparticles comprising the conjugate-based prodrugs. Additionally, the invention also provides non-conjugated antifungal and antibacterial agents in the form of nanoparticles.
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Paragraph 0431
(2015/01/06)
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- Combinatorial synthesis of PEG oligomer libraries
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A simple chain-extending approach was established for the scale-up of the monoprotected monodisperse PEG diol materials. Reactions of THP-(OCH2CH2)n—OMs (n=4, 8, 12) with a large excess of commercially available H—(OCH2CH2)n—OH (n=1-4) under basic conditions led to THP-(OCH2CH2)n—OH (n=5-15). Similarly, Me-(OCH2CH2)n—OH (n=4-11, 13) were prepared from Me-(OCH2CH2)n—OMs (n=3, 7, 11). For the chain elongation steps, 40-80% yields were achieved through extraction purification. PEG oligomer libraries I and II were generated in 50-95% overall yields by alkylation or acylation of THP-(OCH2CH2)n—OH (n=1-15) followed by deprotection. Alkylation of Me-(OCH2CH2)n—OH (n=1-11, 13) with X—(CH2)m—CO2R (X=Br or OMs) and subsequent hydrolysis led to PEG oligomer library III in 30-60% overall yields. Combinatorial purification techniques were adapted to the larger-scale library synthesis. A total of 498 compounds, each with a weight of 2-5 g and a minimum purity of 90%, were synthesized.
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Page/Page column 11
(2010/02/15)
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