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| ln Vitro |
In several cellular models of estrogen receptor function, 27-hydroxycholesterol, an endogenous selective modulator of estrogen receptors, exhibits notable partial agonist activity. In cell models of breast cancer, it actively controls transcription of genes and proliferation of cells [1]. By activating estrogen receptors, 27-hydroxycholesterol has a negative impact on prostate cancer cell lines. Estrogen receptor inhibitors can mitigate the considerable increase in cell proliferation caused by 27-hydroxycholesterol in LNCaP and PC3 cells [2]. Intracellular cholesterol homeostasis is regulated by 27-hydroxycholesterol, an oxysterol that is generated from cholesterol by the monooxygenase CYP27A1. In addition to its role as an endogenous selective estrogen receptor modulator, 27-hydroxycholesterol has the ability to promote the growth and spread of breast cancer. The tumor-promoting potential of CYP27A1 can be reduced by statins or direct inhibition of the enzyme, which lowers the levels of 27-hydroxycholesterol [3]. When there is an excess of cholesterol, one major route for LXR activation is the 27-hydroxylation of cholesterol [4].
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| References |
[1]. DuSell CD, et al. 27-hydroxycholesterol is an endogenous selective estrogen receptor modulator. Mol Endocrinol. 2008 Jan;22(1):65-77.
[2]. Raza S, et al. The cholesterol metabolite 27-hydroxycholesterol stimulates cell proliferation via ERβ in prostate cancer cells. Cancer Cell Int. 2017 May 11;17:52. [3]. Kimbung S, et al. Impact of 27-hydroxylase (CYP27A1) and 27-hydroxycholesterol in breast cancer. Endocr Relat Cancer. 2017 Jul;24(7):339-349. [4]. Fu X, et al. 27-hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells. J Biol Chem. 2001 Oct 19;276(42):38378-87 |
| Additional Infomation |
(25R)-Cholesterol-5-en-3β,26-diol is a 26-hydroxycholesterol with an R configuration at carbon 25. It induces apoptosis, provides neuroprotection, and has metabolic effects in both humans and mice. Its function is related to cholesterol. 27-Hydroxycholesterol is an endogenous metabolite of cholesterol, produced by the hydroxylation of the 27-carbon atom catalyzed by mitochondrial sterol 26-hydroxylase (CYP27A1). Some tumors produce excessive amounts of 27-hydroxycholesterol (27HC) or inhibit its catabolism; high cholesterol levels are associated with elevated 27HC levels. In such cases, 27HC may possess harmful selective estrogen receptor modulator (SERM) and hepatic X receptor (LXR) agonist activities. As a selective estrogen receptor modulator (SERM), 27HC binds to and inhibits the activation of estrogen receptors (ER) in blood vessels. This prevents ER-mediated vasodilation, thereby negating the cardiovascular protective effects of estrogen. However, 27HC can bind to and activate ER and LXR in breast tissue, thereby stimulating the growth and metastasis of ER-dependent breast cancer cells.
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| Molecular Formula |
C27H46O2
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|---|---|
| Molecular Weight |
402.6529
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| Exact Mass |
402.349
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| CAS # |
20380-11-4
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| PubChem CID |
123976
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| Appearance |
White to off-white solid powder
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
517.1±23.0 °C at 760 mmHg
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| Flash Point |
215.6±17.2 °C
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| Vapour Pressure |
0.0±3.1 mmHg at 25°C
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| Index of Refraction |
1.538
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| LogP |
7.84
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
29
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| Complexity |
612
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| Defined Atom Stereocenter Count |
9
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| SMILES |
O([H])[C@@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])C(C1([H])[H])=C([H])C([H])([H])[C@]1([H])[C@]2([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@@]([H])([C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[H])C([H])([H])O[H])C([H])([H])C([H])([H])[C@]21[H]
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| InChi Key |
FYHRJWMENCALJY-YSQMORBQSA-N
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| InChi Code |
InChI=1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
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| Chemical Name |
(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
Ethanol : ~16.67 mg/mL (~41.40 mM)
DMSO : ~1 mg/mL (~2.48 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 1 mg/mL (2.48 mM) in 10% EtOH + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear EtOH stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1 mg/mL (2.48 mM) (saturation unknown) in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear EtOH stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 1 mg/mL (2.48 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: ≥ 1 mg/mL (2.48 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear EtOH stock solution to 900 μL of corn oil and mix well. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4835 mL | 12.4177 mL | 24.8355 mL | |
| 5 mM | 0.4967 mL | 2.4835 mL | 4.9671 mL | |
| 10 mM | 0.2484 mL | 1.2418 mL | 2.4835 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT04101643 | UNKNOWN STATUS | Drug: evolocumab | Hereditary Spastic Paraplegia Type 5 | First Affiliated Hospital of Fujian Medical University | 2019-09-29 | Phase 1 Phase 2 |
| NCT02314208 | COMPLETED | Drug: Xenbilox Dietary Supplement: Resveratrol Drug: Tahor |
Spastic Paraplegia, Hereditary | Institut National de la Santé Et de la Recherche Médicale, France |
2015-01 | Phase 2 |
| NCT02259153 | COMPLETED | Behavioral: Changes in cholesterol metabolism Other: Lean red meat diet Other: Fat red meat diet |
Cholesterol Diet, High-Fat Fatty Acids Hyperlipidemias |
Instituto Aragones de Ciencias de la Salud | 2014-03 | Not Applicable |
| NCT01180361 | RECRUITING | Rheumatoid Arthritis | NYU Langone Health | 2008-09 | ||
| NCT05110547 | UNKNOWN STATUS | Idiopathic Parkinson Disease Parkinsonian Syndrome |
Niemann-Pick Disease, Type C | Centre Hospitalier Universitaire Dijon | 2021-04-27 |
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