3381-56-4Relevant academic research and scientific papers
Sensitized photooxygenation of cholesterol and pseudo-cholesterol derivatives via singlet oxygen
Shuping, Wu,Zhiqin, Jiang,Heting, Li,Li, Yang,Daixun, Zeng
, p. 52 - 60 (2001)
3-Substituted cholesterols and 7-substituted pseudocholesterols undergo a facile photooxygenation sensitized by 9, 10-dicyanoanthracene (DCA) and lumiflavin (LF) to give similar, oppositely-positioned enol derivatives. Both steroids showed the same reaction pattern associated with the endocyclic 5- and 4-olefin units, respectively. The reaction was proposed to proceed via the ene reaction of singlet oxygen and subsequent rearrangement of the initially formed 5α-hydroperoxides.
2-(2-Cholesteroxyethoxyl)ethyl 3′-S-glutathionylpropionate and its self-assembled micelles for brain delivery: Design, synthesis and evaluation
Najmi, Asim,Wang, Shenggang,Huang, Yue,Seefeldt, Teresa,Alqahtani, Yahya,Guan, Xiangming
, (2021/04/09)
The blood–brain barrier (BBB) is a barrier that prevents almost all large and most small exogenous molecules from reaching the brain. The barrier is the major cause of treatment failure for most brain diseases. Extensive efforts have been made to facilitate drug molecules to cross the BBB. One of the approaches is to employ an endogenous ligand or ligand analogue that can enter the brain through its transporter or receptor at the BBB as a brain-targeting agent. Glutathione (GSH) transporters are richly expressed at the BBB with limited presence in other tissues except kidneys. 2-(2-Cholesteroxyethoxyl)ethyl 3′-S-glutathionylpropionate (COXP), formed by connecting GSH with cholesterol through a linker, was designed as a GSH transporter-mediated brain targeting molecule. The amphiphilic nature of COXP enables the molecule to self-assemble to form micelles with a CMC value of 3.9 μM. By using DiR as a fluorescence tracking agent and the whole-body fluorescence imaging technique, the brain distribution of DiR delivered by COXP micelles in mice was 20 folds higher when compared with free DiR. Interestingly, the brain targeting effect was further enhanced by co-administration of GSH. The low CMC value and effective brain targeting make COXP micelles a promising drug delivery system to the brain.
Preparation and application of brain glioma targeting berberine and folic acid modified lipid material
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Paragraph 0010; 0027, (2021/09/21)
The invention discloses preparation and application of a brain glioma targeting berberine and folic acid modified lipid material, and can be used for preparing lipidosome modified by brain glioma targeting Tween 80 coated berberine and folic acid. The liposome surface is coated with Tween 80 and can pass through the blood-brain barrier effectively through receptor-mediated endocytosis after binding with low density lipoprotein receptors to deliver the drug to the brain. In addition, the liposome uses folic acid and berberine to modify brain glioma targeting and mitochondrial targeting capacity of the liposome, and the long chain of polyethylene glycol is introduced to stabilize the liposome. A new thought and a method can be provided for targeted therapy of glioma, and a wide application prospect is provided. pH MDR. The utility model can provide a new idea and a method for targeted therapy of brain glioma.
Preparation and application of three-branch RGD modified brain glioma targeting lipid material
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Paragraph 0028, (2021/11/03)
The invention discloses a three-branch RGD-modified glioma targeting lipid material which is used for targeted delivery of brain glioma treatment drugs. One end of the novel lipid material is connected with cholesterol extending through polyethylene glycol, and the other end of the novel lipid material is connected with RGD peptide with brain glioma targeting function, and the novel lipid material can be used for integrin receptor α which is highly expressed on the surface of brain capillary endothelial cells and brain glioma cells. v β3 The affinity between the brain glioma is achieved through the affinity between the brain glioma, and the effective concentration of the therapeutic drug to the brain tumor is improved. The novel lipid lipid material can be used for liposome. The prepared paclitaxel liposome has obvious brain targeting property and tumor targeting property, and has wide application prospects.
GLUTATHIONE-CHOLESTEROL DERIVATIVES AS BRAIN TARGETING AGENTS
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Paragraph 0108-0112, (2020/02/27)
The present invention describes compositions containing cholesterol-linker-glutathione conjugates for targeting the brain by overcoming barrier entry to the CNS through the blood brain barrier (BBB), including micelle and liposome forms of such compositions. In addition, methods for treating subjects by administering such compositions are also disclosed.
Preparation and application of multi-branch biotin modified breast cancer targeted liposomes
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Paragraph 0026, (2020/04/09)
The invention discloses novel lipid materials for realizing the delivery of breast cancer targeted drugs. According to the novel lipid materials, through a branch framework, one end is connected to cholesterol extended by polyethylene glycol, and the other end is connected to a different number of biotins with a breast cancer targeting function; and affinity between the novel lipid materials and areceptor can be used to realize stronger tumor targeting and play a more effective role in breast cancer treatment. The novel lipid materials can be used in different dosage forms such as liposomes,nanoparticles and micelles, and the prepared paclitaxel-loaded liposomes have obvious breast cancer targeting and broad application prospects.
Biotin and membrane-penetrating peptide CO-mediated intelligent liposome material for breast cancer targeting (by machine translation)
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Paragraph 0024, (2020/06/16)
The invention discloses a breast cancer targeting intelligent liposome material which is jointly mediated by biotin and a membrane penetrating peptide. After the liposome reaches the breast tumor part, PEG long-chain rupture of the hydrazone key is removed, and the short-chain-connected R8-mediated transmembrane is exposed, so that the effect of effectively treating the breast cancer is achieved through Michahael adducts. R8; 2; after the liposome reaches the mammary gland tumor site, the liposome is exposed out of the short-chain-linked immunostimulatory SMVT transposon. The novel intelligent lipid material can be used for different dosage forms including liposomes, nanoparticles, micelles and the like, and the prepared paclitaxel liposome has strong breast cancer penetration and treatment effects and has a wide application prospect. (by machine translation)
Preparation and application of breast cancer targeted liposome modified by biotin and glucose
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Paragraph 0028, (2020/03/11)
The invention discloses a novel lipid material for realizing the delivery of a breast cancer targeted drug. The novel lipid material takes lysine as a connecting group and is connected with a cholesteric part, a biotin part and a glucose part. The affinity between biotin and glucose in the novel lipid material and biotin transporter (SMVT) and glucose transporter (GLUT1) can be utilized to realizethe double targeting function to breast cancer and play a stronger breast cancer targeting therapeutic role, wherein the biotin transporter (SMVT) and the glucose transporter (GLUT1) are highly expressed on the surface of breast cancer cells. The novel lipid material can be used in different dosage forms comprising liposomes, nanoparticles, micelles and the like, and the prepared paclitaxel-loaded liposome has obvious breast cancer targeting property and a wide application prospect.
Biotin and glucose dual-targeting, ligand-modified liposomes promote breast tumor-specific drug delivery
Fu, Qiuyi,Guo, Li,Huang, Mengyi,Peng, Yao,Pu, Yanchi,Wu, Yong,Zheng, Yongxiang
supporting information, (2020/04/21)
Breast cancer is the second leading cause of cancer-related deaths in women. Ligand-modified liposomes are used for breast tumor-specific drug delivery to improve the efficacy and reduce the side effects of chemotherapy; however, only a few liposomes with high targeting efficiency have been developed because the mono-targeting, ligand-modified liposomes are generally unable to deliver an adequate therapeutic dose. In this study, we designed biotin-glucose branched ligand-modified, dual-targeting liposomes (Bio-Glu-Lip) and evaluated their potential as a targeted chemotherapy delivery system in vitro and in vivo. When compared with the non-targeting liposome (Lip), Bio-Lip, and Glu-Lip, Bio-Glu-Lip had the highest cell uptake in 4T1 cells (3.00-fold, 1.60-fold, and 1.95-fold higher, respectively) and in MCF-7 cells (2.63-fold, 1.63-fold, and 1.85-fold higher, respectively). The subsequent cytotoxicity and in vivo assays further supported the dual-targeting liposome is a promising drug delivery carrier for the treatment of breast cancer.
Deep-Red-Fluorescent Zinc Probe with a Membrane-Targeting Cholesterol Unit
Hong, Jayeon,Kim, Jin Ju,You, Youngmin,Yu, Seungyeon
, p. 11562 - 11576 (2020/09/09)
Organelle-targeting fluorescence probes are valuable because they can provide spatiotemporal information about the trafficking of analytes of interest. The spatiotemporal resolution can be improved by using low-energy emission signals because they are barely contaminated by autofluorescence noises. In this study, we designed and synthesized a deep-red-fluorescent zinc probe (JJ) with a membrane-targeting cholesterol unit. This zinc probe consists of a boron-azadipyrromethene (aza-BODIPY) fluorophore and a zinc receptor that is tethered to a tri(ethylene glycol)-cholesterol chain. In aqueous solutions buffered to pH 7.4, JJ exhibits weak fluorescence with a peak wavelength of 663 nm upon excitation at 622 nm. The addition of ZnCl2 elicits an approximately 5-fold enhancement of the fluorescence emission with a fluorescence dynamic range of 141000. Our electrochemical and picosecond transient photoluminescence investigations indicate that the fluorescence turn-on response is due to the zinc-induced abrogation of the formation of a nonemissive intramolecularly charge-separated species, which occurs with a driving force of 0.98 eV. The fluorescence zinc response was found to be fully reversible and to be unaffected by pH changes or the presence of biological metal ions. These properties are due to tight zinc binding with a dissociation constant of 4 pM. JJ was found to be nontoxic to HeLa cells up to submicromolar concentrations, which enables cellular imaging. Colocalization experiments were performed with organelle-specific stains and revealed that JJ is rapidly internalized into intracellular organelles, including lysosomes and endoplasmic reticula. Unexpectedly, probe internalization was found to permeabilize the cell membrane, which facilitates the influx of exogens such as zinc ions. Such permeabilization does not arise for a control probe without the tri(ethylene glycol)-cholesterol chain (JJC). Our results show that the membrane-targeting cholesterol unit can disrupt membrane integrity.
