11-cis-Retinoic Acid-d5

11-cis-Retinoic Acid-d5 is the deuterium labeled Retinoic acid. Retinoic acid is a metabolite of vitamin A that plays important roles in cell growth, differentiation, and organogenesis. Retinoic acid is a natural agonist of RAR nuclear receptors, with IC50s of 14 nM for RARα/β/γ. Retinoic acid bind to PPARβ/δ with Kd of 17 nM. Retinoic acid acts as an inhibitor of transcription factor Nrf2 through activation of retinoic acid receptor alpha[1][2].

Product Specifications

UNSPSC

12352211

Target

Autophagy; Endogenous Metabolite; Isotope-Labeled Compounds; PPAR; RAR/RXR

Type

Isotope-Labeled Compounds

Related Pathways

Autophagy; Cell Cycle/DNA Damage; Metabolic Enzyme/Protease; Others; Vitamin D Related/Nuclear Receptor

Field of Research

Cancer

Solubility

10 mM in DMSO

Smiles

OC(/C=C(C)/C=C\C=C(C)\C=C\C1=C(C([2H])([2H])[2H])C([2H])([2H])CCC1(C)C)=O

Molecular Formula

C20H23D5O2

Molecular Weight

305.47

References & Citations

[1]Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019;53 (2) :211-216. |[2]Wu L, et al. Retinoid X Receptor Agonists Upregulate Genes Responsible for the Biosynthesis of All-Trans-Retinoic Acid in Human Epidermis. PLoS One. 2016 Apr 14;11 (4) :e0153556.|[3]Kam RK, et al. Retinoic acid synthesis and functions in early embryonic development. Cell Biosci. 2012 Mar 22;2 (1) :11.|[4]Shaw N, et al. Retinoic acid is a high affinity selective ligand for the peroxisome proliferator-activated receptor beta/delta. J Biol Chem. 2003 Oct 24;278 (43) :41589-92.|[5]Apfel C, et al. A retinoic acid receptor alpha antagonist selectively counteracts retinoic acid effects. Proc Natl Acad Sci U S A. 1992 Aug 1;89 (15) :7129-33.|[6]Yu S, et al. Retinoic acid induces neurogenesis by activating both retinoic acid receptors (RARs) and peroxisomeproliferator-activated receptor β/δ (PPARβ/δ) . J Biol Chem. 2012 Dec 7;287 (50) :42195-205.|[7]Xiu Jun Wang, et al. Identification of retinoic acid as an inhibitor of transcription factor Nrf2 through activation of retinoic acid receptor alpha. Proc Natl Acad Sci U S A. 2007 Dec 4;104 (49) :19589-94.