A selective LXR modulator and ChEH inhibitor
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Dendrogenin A

Item No. 37975

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β,5α,6β)-6-[[2-(1H-imidazol-5-yl)ethyl]amino]-cholestane-3,5-diol
CAS Number
1191043-85-2
Synonyms
  • DDA
Molecular Formula
C32H55N3O2
Formula Weight
513.8
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/ml
SMILES
C[C@@]([C@@]1(C2)O)(CC[C@@H]2O)[C@](CC3)([H])[C@](C[C@H]1NCCC4=CN=CN4)([H])[C@@](CC[C@]5([H])[C@H](C)CCCC(C)C)([H])[C@]35C
InChi Code
InChI=1S/C32H55N3O2/c1-21(2)7-6-8-22(3)26-9-10-27-25-17-29(34-16-13-23-19-33-20-35-23)32(37)18-24(36)11-15-31(32,5)28(25)12-14-30(26,27)4/h19-22,24-29,34,36-37H,6-18H2,1-5H3,(H,33,35)/t22-,24+,25+,26-,27+,28+,29-,30-,31-,32+/m1/s1
InChi Key
AVFNYTPENXWWCA-BULFVYHESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Dendrogenin A (DDA) is a selective liver X receptor (LXR) modulator (SLiM), an inhibitor of cholesterol epoxide hydrolase (ChEH; Ki = 120 nM), and an active metabolite of cholesterol.1,2 It is formed from 5,6α-epoxy cholesterol via conjugation with histamine by DDA synthase.2,1,3 DDA is found in non-cancerous human mammary epithelial cells and epithelial melanocytes but not in a variety of breast carcinoma or melanoma cells and only at low levels in isolated human breast tumor tissue.2 It inhibits 22(R)-hydroxy cholesterol-induced activation of LXRβ and LXRα in a reporter assay (IC50s = 76 and 362 nM, respectively) but is also a partial agonist of LXRs, increasing protein levels of Nur77, NOR-1, LC3-I, and LC3-II in B16/F10 murine melanoma cells.4 It is selective for modulation of LXRα and LXRβ over the pregnane X receptor (PXR), aryl hydrocarbon receptor (AhR), vitamin D receptor (VDR), retinoid X receptor γ (RXRγ), retinoic acid receptor α (RARα), peroxisome proliferator-activated receptor α (PPARα), PPARγ, glucocorticoid receptor, androgen receptor, estrogen receptor α (ERα), and ERβ at 2.5 µM. It also increases protein levels of LC3-II in B16/F10 and SK-MEL-28 cancer cells when used at concentrations of 2.5 and 5 µM and induces autophagic cell death in the same cell types at 2.5 µM. DDA (0.37 µg/kg) reduces tumor growth in a B16/F10 murine model of melanoma and a TS/A murine mammary cancer model and induces cancer cell differentiation in vitro and in vivo.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Poirot, M., and Silvente-Poirot, S. The tumor-suppressor cholesterol metabolite, dendrogenin A, is a new class of LXR modulator activating lethal autophagy in cancers. Biochem. Pharmacol. 153, 75-81 (2018).

    2. de Medina, P., Paillasse, M.R., Segala, G., et al. Dendrogenin A arises from cholesterol and histamine metabolism and shows cell differentiation and anti-tumour properties. Nat. Commun. 4, 1840 (2013).

    3. Soulès, R., Audouard-Combe, F., Huc-Claustre, E., et al. A fast UPLC-HILIC method for an accurate quantification of dendrogenin A in human tissues. J. Steroid Biochem. Mol. Biol. 194, 105447 (2019).

    4. Segala, G., David, M., de Medina, P., et al. Dendrogenin A drives LXR to trigger lethal autophagy in cancers. Nat. Commun. 8(1), 1903 (2017).