1510-21-0Relevant articles and documents
Cholesterol-linked β-cyclodextrin - A thermotropic liquid-crystalline derivative
Shaikh, Vasi Ahmed Ebrahim,Lonikar, Shrikant Vitthal,Dhobale, Deepa Arun,Pawar
, p. 1975 - 1980 (2007)
Liquid-crystalline derivative of β-cyclodextrin (BCD) was prepared by covalent linking of monocholesteryl succinate (ChMS) with β-cyclodextrin. To the best of our knowledge, this was first ever attempt so far of its kind, in which BCD has been converted into its liquid-crystalline derivative through covalent linkage of a mesogen. The degree of substitution (DS) obtained was ≈2.00. The product was characterized by various techniques, such as FT-IR, NMR, DSC, hot-stage-coupled optical polarizing microscopy (OPM), microanalysis and chemical methods. Cholesterol-linked β-cyclodextrin (CDCh) derivative was found to exhibit thermotropic liquid-crystalline behavior. The product exhibited birefringence during first heating above 130°C, and it became isotropic at about 180°C, whereas the parent compound BCD decomposed without melting above 250 °C. A comparison of CDCh derivative to similar liquid-crystalline poly-saccharide derivatives is presented.
A novel truncated basic fibroblast growth factor fragment-conjugated poly (ethylene glycol)-cholesterol amphiphilic polymeric drug delivery system for targeting to the FGFR-overexpressing tumor cells
Cai, Lulu,Qiu, Neng,Li, Xia,Luo, Kaili,Chen, Xiang,Yang, Li,He, Gu,Wei, Yuquan,Chen, Lijuan
, p. 173 - 182 (2011)
Targeted uptake of therapeutic nanoparticles in tumor cells-specific manner represents a potentially powerful technology in cancer therapy. In present study, we proposed a drug delivery system formulated with biocompatible and biodegradable cholesterol-block-poly (ethylene glycol) (Chol-PEG 2000-COOH) polymer. And the surface of the polymer was chemically linked with truncated bFGF fragments (tbFGF). The tbFGF could recognize fibroblast growth factor receptors (FGFR) that are highly expressed by a variety of human cancer cells. The micelles had a size distribution of about 10-50 nm and significantly enhanced the cytotoxicity of paclitaxel to LL/2 cells as demonstrated by MTT test (IC50 = 0.21 μg/mL for tbFGF conjugated Chol-PEG2000-COOH micelles (tbFGF-M-PTX) versus 26.43 μg/mL for free paclitaxel, respectively). Flow cytometry revealed the cellular uptake of rhodamine B encapsulated in the tbFGF-conjugated micelles was increased by 6.6-fold for HepG2, 6.2-fold for A549, 2.9-fold for C26 and 2.7-fold for LL/2 tumor cells, respectively, compared with micelles without tbFGF. The fluorescence spectroscopy images further demonstrated that the tbFGF conjugated micelles could specifically bind to the tumor cells that over-expressed FGFRs and then release rhodamine B into the cytoplasm. Our results suggest the tbFGF conjugated Chol-PEG2000-COOH micelles have great potential application for tumor targeting therapy.
Poly(N-propargylamide)s bearing cholesteryl moieties: Preparation and optical activity
Zhang, Chaohong,Liu, Dong,Zhou, Bolin,Deng, Jianping,Yang, Wantai
, p. 832 - 838 (2012)
We synthesized a novel chiral cholesteryl-based N-propargylamide (M ch, HCCCH2NHCOCH2CH2COOch, ch = cholesteryl) from which homopolymers [P(Mch)] with different molecular weights (number-average molecular weight: 8600, 14100 and 30000) were prepared. The polymers formed helical structures with a preferential helicity. The three polymers increased in both helix content and specific rotation as the molecular weight increased. P(Mch)-8600 was studied in detail as the model polymer. P(Mch)-8600 adopted helical conformations in toluene, THF, CHCl3 and CH2Cl2, exhibited thermal stability with a decomposition temperature of 273°C and formed a lyotropic liquid crystal under the studied conditions. Copolymers of different compositions of Mch and an achiral monomer (Met) were prepared. The copolymers formed helices to different degrees depending on the specific composition, indicating an effective approach for controlling the formation of helices in synthetic helical polymers.
Design and synthesis of new cholesterol-conjugated 5-fluorouracil: A novel potential delivery system for cancer treatment
Radwan, Awwad A.,Alanazi, Fares K.
, p. 13177 - 13187 (2014)
Cholesterol-conjugated 5-fluorouracil prodrugs were designed to be carried in vivo via low density lipoproteins (LDL) and subsequently undergo LDL-receptor-mediated internalisation into cancer cells. In vivo anti-cancer evaluation was performed using 5-fluorouracil-cholesterol conjugate in a mouse model. The obtained prodrugs were more potent than 5-fluorouracil control drug at the same 5-fluorouracil content (3 mg·kg-1).
Matrix-molecule induced chiral enhancement effect of binary supramolecular liquid crystals
Ma, Xiao-Jing,Shen, Yong-Tao,Deng, Ke,Tang, Hong,Lei, Sheng-Bin,Wang, Chen,Yang, Yan-Lian,Feng, Xi-Zeng
, p. 4699 - 4704 (2007)
Chiral enhancement effects associated with supramolecular liquid crystalline structures are studied, using a complex of achiral molecules (4,4′-bipyridine, 4Bpy) and chiral cholesteric liquid crystalline molecules (3-cholesteryloxycarbonylpropanoic acid, C4) as the model system. Non-mesogenic achiral molecule 4Bpy is used as the matrix element. The chiral enhancement of the supramolecular liquid crystalline structures can be revealed by circular dichroism (CD) and helical twisting power measurements. It is interesting that CD spectra of the complex exhibited an appreciably enhanced chiral property in comparison with that of the pure chiral cholesteric C4 molecules at room temperature. The helical pitch measurements by the Grandjean-Cano method also confirm the chiral enhancement effect. In addition, polarizing optical microscopy (POM) measurements indicate that the addition of matrix molecules leads to the explicit expression of the chiral liquid crystalline texture, i.e. twisted grain boundary (TGBA*) phase, at the liquid crystal temperature. Differential scanning calorimetry (DSC) and variable-temperature X-ray diffraction measurements further confirm the existence of the TGBA* phase. The binary supramolecular assembly structures are investigated by scanning tunneling microscope (STM) and the formation of hydrogen bonds between the chiral mesogens and the achiral matrix molecules can be directly observed. The variable-temperature Fourier transform infrared (FTIR) results further demonstrate that the hydrogen bonds persist until 168 °C. These results indicate that the introduction of a bifunctional aromatic base such as bipyridine could lead to self-assembled supramolecular architectures with discernible enhancements of chiral properties. The Royal Society of Chemistry.
Microtubes self-assembled from a cholesterol-modified nucleoside
Pescador, Paula,Brodersen, Nicolai,Scheidt, Holger A.,Loew, Martin,Holland, Gudrun,Bannert, Norbert,Liebscher, Juergen,Herrmann, Andreas,Huster, Daniel,Arbuzova, Anna
, p. 5358 - 5360 (2010)
We describe the formation of lipid microtubes from a novel cholesterol-modified nucleoside in binary mixture with phospholipids. Stable cylindrical structures with an outer diameter of 2-3 μm and a length of 20-40 μm were formed. By varying the preparation conditions, thinner tubules with nanometre-scale diameters could also be obtained.
Synthesis of novel thiol-reactive amphiphilic lipids based on cholesterol for protein-liposome coupling
Kley, Joerg T.,Fichert, Thomas,Massing, Ulrich
, p. 319 - 327 (1998)
The synthesis of a series of coupling lipids designed for covalently linking proteins to liposomes is described. The new compounds have in common a cholesterylsuccinyl unit as a lipid anchor and a thiol-reactive maleimidobenzoyl unit which are linked by alkyl or (poly)ethylene glycol spacers that differ in length and polarity.
Synthesis of cationic cholesterol derivatives with succinyl spacer group
Konstantinova,Klykov,Maslov,Serebrennikova
, p. 1189 - 1191 (2002)
Syntheses of N, N, N-trimethyl [2-(3β-cholesteryloxy) syccinyloxyethyl] ammonium iodide, N,N-dimethyl-N-2-hydroxyethyl [2-(3β-cholesteryloxy)syccinyloxyethyl]ammonium iodide, and N-[(3β-cholesteryloxy)syccinyl]piperazine were performed. The compounds synthesized in a liposomal form may be used for delivery of genetical material into cells.
Synthesis of α-carboranyl-α-acyloxy-amides as potential BNCT agents
Jonnalagadda, Subash C.,Cruz, Jonathan S.,Connell, Ryan J.,Scott, Patricia M.,Mereddy, Venkatram R.
, p. 4314 - 4317 (2009)
Novel α-carboranyl-α-acyloxy-amides were prepared as potential BNCT agents utilizing three-component Passerini reaction. Preliminary cytotoxicity of the representative compounds on two brain tumor cell lines (U-87 and A-172) showed no effect on cell viability; an essential requirement for utility as potential BNCT agents.
In-plane modulated smectic ? vs smectic 'A' lamellar structures in poly(ethyl or propyl ether imine) dendrimers
Kumar, Prabhat,Shankar Rao,Krishna Prasad,Jayaraman
, p. 98 - 104 (2016)
A pair of first and second generation poly(alkyl ether imine) dendrimers is prepared, having covalently attached cholesteryl moieties at their peripheries. The pairs in each generation differ in the alkyl-linker which constitute the dendritic core moieties, even when the number of cholesteryl moieties remains uniform in each pair. The dendrimer pairs are two first and second generation poly(ethyl ether imine) and poly(propyl ether imine) dendrimers, modified with 4 and 8 cholesteryl esters at the peripheries in each pair, respectively. The dendrimer pairs exhibit differing thermotropic mesophase properties. Microscopic, thermal and X-ray diffraction studies reveal a lamellar mesophase for the first generation ethyl-, first and second generation propyl-linker dendrimers. Whereas, the second generation ethyl-linker dendrimer exhibits a layered structure with a superimposed in-plane modulation, the length of which corresponds to a rectangular column width. The role of the dendrimer core moieties with differing linkers in modifying the mesophase properties is studied.
