Retinoic acid
Chemical Name: 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2E,4E,6E,8E,-nonatetraenoic acid
Purity: ≥98%
Biological Activity
Retinoic acid is an endogenous agonist for retinoic acid receptors (IC50 = 14 nM for RARα, RARβ and RARγ receptors). Retinoic acid specifies anterior-posterior patterning of neural progenitors. It promotes differentiation of mouse embryonic stem cells (ESCs) into adipocytes, neurons and glia in vitro. Retinoic acid also promotes differentiation of human PSCs into dopaminergic neurons and maturation of retinal organoids. It is a proposed ligand of RORβ (Kd = 280 nM). Activates autophagy.For more information about how Retinoic acid may be used, see our protocols: Generation of β cells from hPSCs, Cultivating Cerebral Organoids.
Scientific Data
IBJ6 human fibroblast induced pluripotent stem cells which have been differentiated into motor neurons. Performed using a combination of LDN 193189 (100 nM) (Catalog # 6053,Tocris) and SB 431542 (Catalog # 1614, Tocris) followed by Retinoic acid and Purmorphamine (Catalog # 4551, Tocris) culture on Laminin for 18 days. Commitment to the motor neuron fate was assessed using the motor neuron marker anti-Human Islet-1 (red, Catalog # AF1837, R&D Systems) and the general neuronal marker, beta III tubulin (green, Catalog # MAB1195, R&D Systems). For visualization, the neurons were stained using Northernlights™ 557-conjugated Donkey anti-Goat Secondary Antibody (Catalog # NL001, R&D Systems) and Northernlights™ 493-conjugated Donkey anti-Mouse Secondary Antibody (Catalog # NL009, R&D Systems) and counterstained with DAPI (blue, Catalog # 5748, Tocris).
Technical Data
The technical data provided above is for guidance only.
For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Background References
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High-throughput genotoxicity assay identifies antioxidants as inducers of DNA damage response and cell death.
Fox JT, Sakamuru S, Huang R
Proc. Natl. Acad. Sci. U.S.A., 2012;109(14):5423-8. -
Retinoids induce integrin-independent lymphocyte adhesion through RAR-alpha nuclear receptor activity.
Whelan J, Wang L, Chen J, Metts M, Nasser T, McGoldrick L, Bridges L
Biochem Biophys Res Commun, 2014;454(4):537-542. -
BMP4 is required for the initial expression of MITF in melanocyte precursor differentiation from embryonic stem cells.
Yang J, Wang J, Pan L, Li H, Rao C, Zhang X, Niu G, Qu J, Hou L
Exp Cell Res, 2014;320(1):54-61. -
Differentiation of human pluripotent stem cells into nephron progenitor cells in a serum and feeder free system.
Kang, Minyong, Han, Yong-Mah
PLoS ONE, 2014;9(4):e94888. -
Pharmacological modulation of autophagy: therapeutic potential and persisting obstacles.
Galluzzi et al.
Nat.Rev.Drug.Discov., 2017; -
A retinoic acid receptor alpha antagonist selectively counteracts retinoic acid effects.
Apfel et al.
Proc.Natl.Acad.Sci.U.S.A., 1992;89:7129 -
Differentiation of embryonic stem cells into adipocytes in vitro.
Dani et al.
J. Cell Sci., 1997;110:1279 -
Characterisation of human cellular retinoic acid binding proteins-1 and -2: ligand binding affinities and distribution in skin.
Sanquer and Gilchrest
Arch.Biochem.Biophys., 1994;311:86 -
Generation of Cerebral Organoids from Human Pluripotent Stem Cells
Lancaster et al.
Nat.Protoc., 2015;9:2329 -
Self-organization of axial polarity, inside-out layer pattern, and species-specific progenitor dynamics in human ES cell-derived neocortex.
Kadoshima et al.
Proc.Natl.Acad.Sci.USA., 2013;110:20284 -
All-trans retinoic acid is a ligand for the orphan nuclear receptor RORβ.
Stehlin-Gaon et al.
Nat.Struct.Biol., 2003;10:820
Product Datasheets
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Citations for Retinoic acid
The citations listed below are publications that use Tocris products. Selected citations for Retinoic acid include:
6 Citations: Showing 1 - 6
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Fast Generation of Functional Subtype Astrocytes from Human Pluripotent Stem Cells.
Authors: Li Et al.
Stem Cell Reports 2018;11:998
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Retinoic acid signaling maintains epithelial and mesenchymal progenitors in the developing mouse ureter.
Authors: Bohnenpoll
Sci Rep 2017;7(1):14803
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Prolyl endopeptidase is involved in the degradation of neural cell adhesion molecules in vitro.
Authors: Jaako Et al.
J Cell Sci 2016;129:3792
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Inhibition of PAD4 activity is sufficient to disrupt mouse and human NET formation.
Authors: Lewis Et al.
J Med Food 2015;11:189
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Evolution and functional characterisation of melanopsins in a deep-sea chimaera (elephant shark, Callorhinchus milii).
Authors: Davies Et al.
PLoS One 2012;7:e51276
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Berberine promotes axonal regeneration in injured nerves of the peripheral nervous system.
Authors: Han Et al.
Physiol Behav 2012;15:413
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