OH-Chol
目录号 : GC45534
A cationic cholesterol derivative
Cas No.:191173-82-7
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
OH-Chol is a cationic cholesterol derivative.1 OH-Chol, as a component of lipoplexes with DOPE , has been used for siRNA delivery and gene silencing in MCF-7 cells, as well as in mice via intravenous injection, resulting in lipoplex accumulation in the liver. It has also been used in cationic nanoparticles in combination with Tween 80 to transfect pDNA and siRNA into PC3 mouse xenografts via intratumoral injection and with Tween 80 and folate-PEG2000-DSPE in a KB mouse xenograft model for intratumoral gene delivery.2
References
1. Hattori, Y., Nakamura, M., Takeuchi, N., et al. Effect of cationic lipid in cationic liposomes on siRNA delivery into the lung by intravenous injection of cationic lipoplex. J. Drug. Target 27(2), 217-227 (2019).
2. Hattori, Y. Development of non-viral vector for cancer gene therapy. Yakugaku Zasshi 130(7), 917-923 (2010).
| Cas No. | 191173-82-7 | SDF | |
| Canonical SMILES | C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](C(NCCNCCO)=O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C | ||
| 分子式 | C32H56N2O2 | 分子量 | 500.8 |
| 溶解度 | DMF: 10mg/mL,Ethanol: 10mg/mL,Ethanol:PBS (pH 7.2) (1:6): 0.14mg/mL | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.9968 mL | 9.984 mL | 19.9681 mL |
| 5 mM | 0.3994 mL | 1.9968 mL | 3.9936 mL |
| 10 mM | 0.1997 mL | 0.9984 mL | 1.9968 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Development of non-viral vector for cancer gene therapy
Yakugaku Zasshi 2010 Jul;130(7):917-23.PMID:20606371DOI:10.1248/yakushi.130.917.
Cancer gene therapy has been intensively developed using non-viral vectors, among which cationic liposomes and nanoparticles are the most investigated. Optimal gene therapy for tumors must deliver plasmid DNA (pDNA) or synthetic small interfering RNA (siRNA) to tumor cells with high efficiency and minimal toxicity. We developed new cationic nanoparticles (NP) composed of cholesteryl-3beta-carboxyamidoethylene-N-hydroxyethylamine (OH-Chol) and Tween 80, and evaluated the transfection efficiencies of pDNA and siRNA into human prostate tumor PC-3 xenografts. NP showed effective transfection of pDNA and siRNA when directly injected into the xenografts. For targeted delivery to tumors, vitamin folic acid has been utilized for folate receptor (FR)-mediated drug delivery since FR is frequently overexpressed on many types of human tumors. We developed folate-linked nanoparticles (NP-F) composed of OH-Chol, Tween 80 and folate-poly(ethylene glycol)-distearoylphosphatidylethanolamine conjugate. Tumor growth of FR-positive human nasopharyngeal tumor KB xenografts was significantly inhibited when a complex of NP-F and a therapeutic gene was intratumorally injected. These findings suggested that cationic cholesterol-based nanoparticles are potential non-viral pDNA and siRNA vectors for local tumor treatment.
siRNA delivery into tumor cells by cationic cholesterol derivative-based nanoparticles and liposomes
Biol Pharm Bull 2015;38(1):30-8.PMID:25744455DOI:10.1248/bpb.b14-00526.
Previously, we reported that cationic nanoparticles (NP) composed of diamine-type cholesteryl-3-carboxamide (OH-Chol, N-(2-(2-hydroxyethylamino)ethyl)cholesteryl-3-carboxamide) and Tween 80 could deliver small interfering RNA (siRNA) with high transfection efficiency into tumor cells. In this study, we synthesized new diamine-type cationic cholesteryl carbamate (OH-C-Chol, cholesteryl (2-((2-hydroxyethyl)amino)ethyl)carbamate) and triamine-type carbamate (OH-NC-Chol, cholesteryl (2-((2-((2-hydroxyethyl)amino)ethyl)amino)ethyl)carbamate), and prepared cationic nanoparticles composed of OH-C-Chol or OH-NC-Chol with Tween 80 (NP-C and NP-NC, respectively), as well as cationic liposomes composed of OH-C-Chol or OH-NC-Chol with 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE) (LP-C and LP-NC, respectively) for evaluation of their possible use as siRNA delivery vectors. LP-C and LP-NC/siRNA complexes (lipoplexes) exhibited larger gene silencing effects than NP-C and NP-NC/siRNA complexes (nanoplexes), respectively, in human breast tumor MCF-7 cells, although the NP-C nanoplex showed high association with the cells. In particular, LP-NC lipoplex could induce strong gene suppression, even at a concentration of 5 nM siRNA. From these results, cationic liposomes composed of OH-NC-Chol and DOPE may have potential as gene vectors for siRNA transfection to tumor cells.
Effects of lipid composition in cationic liposomes on suppression of mast cell activation
Chem Phys Lipids 2020 Sep;231:104948.PMID:32717231DOI:10.1016/j.chemphyslip.2020.104948.
We previously showed that cationic liposomes composed of cholesteryl-3β-carboxyamidoethylene-N-hydroxyethylamine (OH-Chol) and 1,2-dioleoyl-sn-glycero-3-phosphatidylethanolamine (DOPE) inhibited mast cell degranulation mediated by the cross-linking of high-affinity IgE receptors (FcεRI). In this study, we prepared three kinds of cationic liposomes composed of OH-Chol and DOPE in different ratios (0.28, 0.60, and 0.86 of OH-Chol in mol ratio, named as L-liposome, M-liposome, and H-liposome, respectively) and investigated their effects on mast cell activation. We found that mast cell degranulation evoked with antigen was inhibited by pretreatment with cationic liposomes in the composite ratio-dependent manner of OH-Chol and that the H-liposome showed the highest inhibitory effect on degranulation among three kinds of liposomes. Store-operated Ca2+ entry, phosphorylation of PI3K and Akt, and IL-4 secretion after antigen stimulation were reduced in dose-dependent manner of each liposome, but there were no differences between H-liposome and M-liposome. Meanwhile, microtubule acetylation, which is involved in the secretory granule transport, was significantly suppressed by H-liposome compared with M-liposome. These data suggested that the lipid composition in cationic liposomes themselves largely influenced the inhibition of mast cell activation as well as the efficiency of gene transfection.
Surface properties of lipoplexes modified with mannosylerythritol lipid-a and tween 80 and their cellular association
Chem Pharm Bull (Tokyo) 2009 Feb;57(2):138-43.PMID:19182402DOI:10.1248/cpb.57.138.
The surface properties of cationic liposomes and lipoplexes largely determine the cellular association and gene transfection efficiency. In this study, we measured the surface properties, such as zeta potentials, surface pH and hydration levels of MHAPC- and OH-Chol-lipoplexes and their cellular association, without and with the modification of biosurfactant mannosylerythritol lipid-A (MEL-A) or Tween 80 (MHAPC=N,N-methyl hydroxyethyl aminopropane carbamoyl cholesterol; OH-Chol=cholesteryl-3beta-carboxyamindoethylene-N-hydroxyethylamine). Compared to OH-Chol-lipoplexes, the higher cellular association of MHAPC-lipoplexes correlated with the significantly higher zeta potentials, lower surface pH levels and "drier" surface, as evaluated by the generalized polarization of laurdan. Both MEL-A and Tween 80 modification of MHAPC-lipoplexes did not significantly change zeta potentials and surface pH levels, while MEL-A modification of OH-Chol-lipoplexes seriously decreased them. MEL-A hydrated the liposomal surface of MHAPC-lipoplexes but dehydrated that of OH-Chol-lipoplexes, while Tween 80 hydrated those of MHAPC- and OH-Chol-lipoplexes. In all, cationic liposomes composed of lipids with secondary and tertiary amine exhibited different surface properties and cellular associations of lipoplexes, and modification with surfactants further enlarged their difference. The strong hydration ability of Tween 80 may relate to the low cellular association of lipoplexes, while the dehydration of MEL-A-modified OH-Chol-lipoplexes seemed to compensate the negative zeta potential for the cellular association of lipoplexes.
Cholesterol effects on a mixed-chain phosphatidylcholine bilayer: a molecular dynamics simulation study
Biochimie 2006 May;88(5):449-60.PMID:16356621DOI:10.1016/j.biochi.2005.10.005.
A molecular dynamics simulation of a mono-cis-unsaturated 1-palmitoyl-2-oleoyl-phosphatidylcholine bilayer containing approximately 22 mol% of cholesterol (POPC-Chol) was carried out for 15 ns. An 8-ns trajectory was analysed to determine the effects of Chol on the membrane properties and compare it with that on the fully saturated 1,2-dimyristoyl-phosphatidylcholine bilayer containing approximately 22 mol% of Chol (DMPC-Chol). The study suggests that the experimentally observed weaker effect of Chol on the POPC than DMPC bilayer might result from a different vertical localisation of the Chol hydroxyl group (OH-Chol) in both bilayers: in the POPC-Chol bilayer, OH-Chol is placed approximately 3 A higher in the bilayer interface than in the DMPC-Chol bilayer. Because of the rigid cis double bond in the beta-chain of POPC, Chol fits worse to the POPC-Chol membrane environment and is pushed up, in effect all Chol ring atoms are, on average, located above the double bond. Both in mono-cis-unsaturated and fully saturated PC bilayers, Chol induces stronger van der Waals interactions among the chains, whereas its interactions with the chains are weak. In contrast to DMPC, the smooth alpha-face of the Chol ring lowers the order of POPC chains, whereas the rough beta-face increases the order.