27-Hydroxycholesterol

27-Hydroxycholesterol
Names
IUPAC 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
Systematic IUPAC name
Cholest-5-ene-3-β,26-diol
Identifiers
20380-11-4
2752
Jmol interactive 3D Image
PubChem 123976
Properties
C27H46O2
Molar mass 402.66 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

27-Hydroxycholesterol (27-HC) is an endogenous oxysterol with multiple biological functions, including activity as a selective estrogen receptor modulator (SERM) (a mixed, tissue-specific agonist-antagonist of the estrogen receptor (ER)) and as an agonist of the liver X receptor (LXR).[1] It is a metabolite of cholesterol that is produced by the enzyme CYP27A1.[1]

A link between high cholesterol and breast cancer has been identified, and it has been proposed that this is due to 27-HC production by CYP27A1.[2] Because of its estrogenic action, 27-HC stimulates the growth of ER-positive breast cancer cells, and has been implicated in limiting the effectiveness of aromatase inhibitors in the treatment of breast cancer.[1] As such, identified CYP27A1 inhibitors, including the marketed drugs anastrozole, fadrozole, bicalutamide, dexmedetomidine, ravuconazole, and posaconazole, have been proposed as potential adjuvant therapies in ER-positive breast cancer.[1]

See also

References

  1. 1 2 3 4 Mast N, Lin JB, Pikuleva IA (2015). "Marketed Drugs Can Inhibit Cytochrome P450 27A1, a Potential New Target for Breast Cancer Adjuvant Therapy". Mol. Pharmacol. 88 (3): 428–36. doi:10.1124/mol.115.099598. PMID 26082378.
  2. Nelson ER, Wardell SE, Jasper JS, Park S, Suchindran S, Howe MK, Carver NJ, Pillai RV, Sullivan PM, Sondhi V, Umetani M, Geradts J, McDonnell DP (2013). "27-Hydroxycholesterol links hypercholesterolemia and breast cancer pathophysiology". Science 342 (6162): 1094–8. doi:10.1126/science.1241908. PMC 3899689. PMID 24288332.



This article is issued from Wikipedia - version of the Thursday, September 03, 2015. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.