- Self-assembled phytosterol-fructose-chitosan nanoparticles as a carrier of anticancer drug
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Self-assembled nanoparticles were synthesized from water-soluble fructose-chitosan, substituted by succinyl linkages with phytosterols as hydrophobic moieties for self-assembly. The physicochemical properties of the prepared self-assembled nanoparticles were characterized by Fourier transform infrared spectroscopy, fluorescence spectroscopy, and transmission electron microscopy. Doxorubicin (DOX), as a model anticancer drug, was physically entrapped inside prepared self-assembled nanoparticles by the dialysis method. With increasing initial levels of the drug, the drug loading content increased, but the encapsulation efficiency decreased. The release profiles in vitro demonstrated that the DOX showed slow sustained released over 48 h, and the release rate in phosphate buffered saline (PBS) solution (pH 7.4) was much slower than in PBS solution (pH 5.5 and pH 6.5), indicating the prepared self-assembled nanoparticles had the potential to be used as a carrier for targeted delivery of hydrophobic anticancer drugs with declined cytotoxicity to normal tissues. Copyright
- Qiu, Yeyan,Zhu, Jun,Wang, Jianting,Gong, Renmin,Zheng, Mingming,Huang, Fenghong
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- Novel long-circulating liposomes consisting of PEG modified β-Sitosterol for gambogic acid delivery
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Long-circulating liposome is an effective formulation in field of cancer treatment. However, high expenditure of formulation and high dose of cholesterol severely restrict its application. In this paper, we developed a method by grafting polyethylene glycol 2000 on β-Sitosterol succinic anhydride ester to obtain relatively cheap polyethylene glycol-β-Sitosterol conjugates, which were used to prepare long-circulating liposome without cholesterol. Gambogic acid which is an effective antitumor ingredient with very short half-life, was used as a model drug to prepare long-circulating liposome in this research. Meanwhile, the characteristics, pharmacokinetics and distribution of this novel long-circulating liposome were also investigated in comparison with other gambogic acid formulations. Polyethylene glycol-β-Sitosterol conjugates were synthesized, different liposomal formulations were also prepared by ethanol injection method, and the obtained nanoparticles were characterized by dynamic light scattering and transmission electron microscope. The longcirculating effect, pharmacokinetics and distribution of gambogic acid in rats were also explored. 1HNMR confirmed that polyethylene glycol-β-Sitosterol conjugates were synthesized successfully. Novel long-circulating liposome was successfully prepared by ethanol injection method attaining a entrapment efficiency of 89.4%, exhibiting a homogeneous particle size of 245.2 nm and -24.3 mV zeta potential with smooth continuous surface. This novel long-circulating liposome demonstrated better long-circulating effect than ordinary long-circulating liposome. The novel long-circulating liposome as-prepared not only could reduce cost of grafting polyethylene glycol on macromolecular phospholipid, but also no cholestrol in preparation was applied, expanding the application of liposome as a formulation in the field of lowering blood lipid. Therefore, polyethylene glycol-β-Sitosterol conjugates are recommended substitute for polyethylene glycol modified phospholipid to prepare long-circulating liposomes.
- Yu, Fan,Tang, Xinhui
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- Effect of a new β-sitosterol analogue on plasma lipid concentrations in rats
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N-Substituted succinamic acid β-sitosteryl ester derivatives were prepared and evaluated. Compounds 1 and 2 were prepared in 76-92% yields by the reaction of β-sitosterol and succinic anhydride, followed by the activation of the resulting acid compound 1 by thionyl chloride or methyl chloroformate, and finally by amination with appropriate amines. Compound 2a (DANA87) was also easily obtained in one step by the direct addition of β-sitosterol to dicyclohexylcarbodiimide (DCC) in 80% yield. Administration of the dietary compound DANA87 resulted in significant decreases in total plasma cholesterol (TC) and low-density lipoprotein (LDL) cholesterol concentrations compared with controls in a rat model. High-density lipoprotein cholesterol and plasma triglyceride levels were not affected. These findings indicate that DANA87 functions as TC and LDL cholesterol-reducing agent.
- Song, Yang-Heon,Hong, Soonil,Lim, Hongsan,Seo, Jinmoo,Chung, Sungjoo,No, Insook,Lee, Kyunghee,Yoon, Michung
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- Enhancement of Antioxidant Activity in O/W Emulsion and Cholesterol-Reducing Capacity of Epigallocatechin by Derivatization with Representative Phytosterols
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In this study, derivatization of epigallocatechin (EGC) by representative phytosterols (stigmasterol and β-sitosterol) was performed employing Steglich esterification. The structural identity and purity of epigallocatechin β-sitosterol (ESi) and epigalloc
- Wang, Shanshan,Fan, Jiawen,Xu, Lujing,Ye, Kai,Shu, Tong,Liu, Songbai
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- STEROL PURIFICATION
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The invention relates to sterol esters and methods for producing purified sterols that can be utilized in methods for producing a lipid nanoparticle.
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Paragraph 0323-0325
(2021/11/13)
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- Epigallocatechin β - sitosterol functional molecule, preparation method and application (by machine translation)
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The invention discloses a epigallocatechin β - sitosterol functional molecules, the functional molecule through the epigallocatechin hydroxy valley sterol succinic acid carboxyl form ester, the epigallocatechin valley sterol connection. The invention also
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Paragraph 0040; 0041
(2019/01/08)
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- Polyamine derivatives of betulinic acid and β-sitosterol: A comparative investigation
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β-Sitosterol and betulinic acid were used in designing their conjugates with selected polyamines bearing either an amide bond, or an ester and an amide bond simultaneously in the target molecule. The synthesized compounds were subjected to basic cytotoxic and antimicrobial tests. The synthetic protocol is described separately for each of the three series of the target amides, because each series of compounds required a different synthetic approach. The cytotoxicity was tested on cells derived from human T-lymphoblastic leukemia, breast adenocarcinoma and cervical cancer, and compared with the tests on normal human fibroblasts. Most of the target compounds (5a-5c, 11a-11c and 16a-16c) showed medium to high cytotoxicity (0.7-7.8 μM), however, in some cases the compounds showed high cytotoxicity even toward normal human fibroblasts (11a-11c). Two compounds of this series (11c and 16c) also displayed antimicrobial activity with high and selective microbe specificity. The compound 11c was potent against Escherichia coli (minimal inhibition concentration (MIC) 6.25 μg mL-1, i.e. 9.75 nM mL-1) and Staphylococcus aureus (MIC 12.5 μg mL-1, i.e. 19.5 nM mL-1), and showed medium activity against Pseudomonas aeruginosa. The compound 16c was highly active against Enterococcus faecalis and S. aureus (both, MIC 3.125 μg mL-1, i.e. 4.22 nM mL-1), both Gram-positive bacteria, however showed only weak activity against E. coli and no activity against P. aeruginosa, both Gram-negative bacteria, which indicates possible microbe specificity of 16c. Comparing β-sitosterol-based series (5a-5c) and betulinic acid series (11a-11c and 16a-16c) of the target compounds, the latter one gave more promising structures. The compounds 11c and 16c showed effects which may be described as multifarious activity (pleiotropic effects).
- Bildziukevich, Uladzimir,Vida, Norbert,Rárová, Lucie,Kolá?, Milan,?aman, David,Havlí?ek, Libor,Dra?ar, Pavel,Wimmer, Zdeněk
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supporting information
p. 27 - 35
(2015/05/27)
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- "nok": A phytosterol-based amphiphile enabling transition-metal-catalyzed couplings in water at room temperature
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The third-generation designer amphiphile/surfactant, "Nok" (i.e., SPGS-550-M; β-sitosterol methoxypolyethyleneglycol succinate), soon to be commercially available from Aldrich, can be prepared in two steps using an abundant plant feedstock and β-sitosterol, together with succinic anhydride and PEG-550-M. Upon dissolution in water, it forms nanomicelles that serve as nanoreactors, which can be characterized by both cryo-TEM and dynamic light scattering analyses. Several transition-metal-catalyzed reactions have been run under micellar conditions to evaluate this surfactant relative to results obtained in nanoparticles composed of TPGS-750-M (i.e., a second-generation surfactant). It is shown that Nok usually affords yields that are, in general, as good or better than those typically obtained with TPGS-750-M, and yet is far less costly.
- Klumphu, Piyatida,Lipshutz, Bruce H.
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p. 888 - 900
(2014/03/21)
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- Synthesis of β-sitosterol-quercetin dyads
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Synthesis of novel β-sitosterol-quercetin dyads 6 and 10 as serum cholesterol lowering agent is described. These compounds were prepared in good yields by the reaction of β-sitosterol and succinic anhydride, followed by the activation of the resulting aci
- Kim, Kwanghyun,Song, Yang-Heon
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scheme or table
p. 405 - 408
(2010/03/04)
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