75014-44-7

Usage

InChI:InChI=1/C33H58O4/c1-24(2)7-6-8-25(3)29-11-12-30-28-10-9-26-23-27(37-22-21-36-20-19-35-18-17-34)13-15-32(26,4)31(28)14-16-33(29,30)5/h9,24-25,27-31,34H,6-8,10-23H2,1-5H3/t25-,27+,28+,29-,30+,31+,32+,33-/m1/s1

Upstream product

• 1182-65-6 cholesteryl p-toluenesulfonate 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 57-88-5 cholesterol 
• 69502-33-6 2-(2-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate 
• 60221-37-6 8-(1H-tetrahydropyran-2-yloxy)-3n₆³-dioxaoctan-1-ol 
• 3381-54-2 cholesterol mesylate 

Downstream Products

• 1325206-38-9 C₅₅H₇₂O₈ 
• 1325206-40-3 C₆₆H₈₆N₂O₁₁ 
• 1325206-41-4 C₆₂H₇₈N₂O₁₁ 
• 890049-64-6 8-(cholest-5-en-3β-yloxy)-3,6-dioxaoctyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 
• 890049-63-5 8-(cholest-5-en-3β-yloxy)-3,6-dioxaoctyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 
• 75025-21-7 8-(5-cholesten-3β-yloxy)-3,6-dioxaoctyl p-toluenesulfonate 

Relevant academic research and scientific papers

Preparation and application of brain glioma targeting berberine and folic acid modified lipid material

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

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.

Biotin and membrane-penetrating peptide CO-mediated intelligent liposome material for breast cancer targeting (by machine translation)

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)

Deep-Red-Fluorescent Zinc Probe with a Membrane-Targeting Cholesterol Unit

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.

Design, preparation and evaluation of different branched biotin modified liposomes for targeting breast cancer

A series of liposome ligands (Bio-Chol, Bio-Bio-Chol, tri-Bio-Chol and tetra-Bio-Chol) modified by different branched biotins that can recognize the SMVT receptors over-expressed in breast cancer cells were synthesized. And four liposomes (Bio-Lip, Bio-Bio-Lip, tri-Bio-Lip and tetra-Bio-Lip) modified by above mentioned ligands as well as the unmodified liposome (Lip) were prepared to study the targeting ability for breast cancer. The cytotoxicity study and apoptosis assay of paclitaxel-loaded liposomes showed that tri-Bio-Lip had the strongest anti-proliferative effect on breast cancer cells. The cellular uptake studies on mice breast cancer cells (4T1) and human breast cancer cells (MCF-7) indicated tri-Bio-Lip possessed the strongest internalization ability, which was 5.21 times of Lip, 2.60 times of Bio-Lip, 1.67 times of Bio-Bio-Lip and 1.17 times of tetra-Bio-Lip, respectively. Moreover, the 4T1 tumor-bearing BALB/c mice were used to evaluate the in vivo targeting ability. The data showed the enrichment of liposomes at tumor sites were tri-Bio-Lip > tetra-Bio-Lip > Bio-Bio-Lip > Bio-Lip > Lip, which were consistent with the results of in vitro targeting studies. In conclusion, increasing the density of targeting molecules on the surface of liposomes can effectively enhance the breast cancer targeting ability, and the branching structure and spatial distance of biotin residues may also have an important influence on the affinity to SMVT receptors. Therefore, tri-Bio-Lip could be a promising drug delivery system for targeting breast cancer.

Efficacious Doxorubicin Delivery Using Glutathione-Responsive Hollow Non-phospholipid Vesicles Bearing Lipoyl Cholesterols

In this study, we developed redox-sensitive vesicles using synthesised lipoyl cholesterol derivatives, a non-ionic surfactant and an optimum level of free cholesterol. Interestingly, concentration-dependent self-assembly was observed by scanning electron microscopy, wherein vesicles manifested as hollow spherical (at 0.15 mm) and triangular (0.50 mm). The redoxresponsive characteristics of the vesicles was probed in the presence of dithiothreitol; they underwent a clear increase in size as observed by dynamic light scattering measurements. These vesicles could easily encapsulate an anticancer drug, doxorubicin, and were observed to be stable in the presence of serum. They showed substantial release of the drug in response to biologically relevant stimulus, that is, glutathione. A toxicity assessment on HeLa and HepG2 cancer cells demonstrated activities of the drug-loaded vesicles comparable to that of free drug, whereas significantly enhanced toxicity and apoptotic induction were observed against drug-resistant HeLa cells, which was determined by studying the cellular internalisation of doxorubicin.

Liposomes actively recognizing the glucose transporter GLUT1 and integrin αvβ3 for dual-targeting of glioma

The treatment of glioma is a great challenge because of the existence of the blood–brain barrier (BBB). In order to develop an efficient glioma-targeting drug delivery system to greatly improve the brain permeability of anti-cancer drugs and target glioma, a novel glioma-targeted glucose-RGD (Glu-RGD) derivative was designed and synthesized as ligand for preparing liposomes to effectively deliver paclitaxel (PTX) to cross the BBB and target glioma. The liposomes were prepared and characterized for particle size, zeta potential, encapsulation efficiency, release profile, stability, hemolysis, and cell cytotoxicity. Also, the Glu-RGD modified liposomes showed superior targeting ability in in vitro and in vivo evaluation as compared to naked PTX, non-coated, singly modified liposomes and liposomes co-modified by physical blending. The relative uptake efficiency and concentration efficiency were enhanced by 4.41- and 4.72-fold compared to that of naked PTX, respectively. What is more, the Glu-RGD modified liposomes also displayed the maximum accumulation of DiD-loaded liposomes at tumor sites compared to the other groups in in vivo imaging. All the results in vitro and in vivo suggested that Glu-RGD-Lip would be a potential delivery system for PTX to treat integrin αvβ3-overexpressing tumor-bearing mice.

Liposomes modified with double-branched biotin: A novel and effective way to promote breast cancer targeting

Although active targeting liposomes with cancer-specific ligands can bind and internalize into cancer cells, only a few high-efficiency liposomes have been developed so far because traditional single branched ligand modified liposomes generally failed to deliver adequate therapeutic payload. In this paper, we broke the traditional design concept and synthesized the double branched biotin modified cholesterol (Bio2-Chol) for the first time. On this basis, different biotin density modified liposomes ((Bio-Chol)Lip, (Bio-Chol)2Lip and (Bio2-Chol)Lip) were successfully prepared and used as active targeting drug delivery systems for the treatment of breast cancer. The in vitro and in vivo breast cancer-targeting ability of these liposomes were systemically studied using paclitaxel (PTX) as the model drug. And the uptake mechanism of (Bio2-Chol)Lip was investigated. The results showed that (Bio2-Chol)Lip had the best breast cancer-targeting ability compared with naked paclitaxel, unmodified Lip, (Bio-Chol)Lip and (Bio-Chol)2Lip. In particular, the relative uptake efficiency (RE) and concentration efficiency (CE) of (Bio2-Chol)Lip were respectively enhanced by 5.61- and 5.06-fold compared to that of naked paclitaxel. Both distribution data and pharmacokinetic parameters suggested that the double branched biotin modified liposome ((Bio2-Chol)Lip) is a very promising drug delivery carrier for breast cancer.

Cholesterol pyrophosphate, and preparation method and use thereof

The invention discloses a cholesterol pyrophosphate, and a preparation method and a use thereof. Cholesterol and pyrophosphate are connected through click chemistry, and the targeting auxiliary material cholesterol pyrophosphate (PPi-Chol) having strong affinity to bones is prepared through combining the wide application of the cholesterol in a medicinal preparation with the bone targeting property of the pyrophosphate, so the studying process of the bone targeting dosage form is greatly improved, and the therapy effect of bone related diseases is improved.

Dual-targeting for brain-specific liposomes drug delivery system: Synthesis and preliminary evaluation

The treatment of glioma has become a great challenge because of the existence of brain barrier (BB). In order to develop an efficient brain targeting drug delivery system to greatly improve the brain permeability of anti-cancer drugs, a novel brain-targeted glucose-vitamin C (Glu-Vc) derivative was designed and synthesized as liposome ligand for preparing liposome to effectively deliver paclitaxel (PTX). The liposome was prepared and its particle size, zeta potential, encapsulation efficiency, release profile, stability, hemolysis and cytotoxicity were also characterized. What's more, the cellular uptake of CFPE-labeled Glu-Vc-Lip on GLUT1- and SVCT2-overexpressed C6 cells was 4.79-, 1.95-, 4.00- and 1.53-fold higher than that of Lip, Glu-Lip, Vc-Lip and Glu + Vc-Lip. Also, the Glu-Vc modified liposomes showed superior targeting ability in vivo evaluation compared with naked paclitaxel, non-coated, singly-modified and co-modified by physical blending liposomes. The relative uptake efficiency was enhanced by 7.53 fold to that of naked paclitaxel, while the concentration efficiency was up to 7.89 times. What's more, the Glu-Vc modified liposomes also displayed the maximum accumulation of DiD-loaded liposomes at tumor sites with the strongest fluorescence in the brain in vivo imaging. Our results suggest that chemical modification of liposomes with warheads of glucose and vitamin C represents a promising and efficient strategy for the development of brain-specific liposomes drug delivery system by utilizing the endogenous transportation mechanism of the warheads.