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.
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Retinoic acid Chemical Structure
CAS No. : 302-79-4
This product is a controlled substance and not for sale in your territory.
Based on 53 publication(s) in Google Scholar
Other Forms of Retinoic acid:
Retinoic acid (Standard)
In-stock
Retinoic acid-d5
In-stock
Retinoic acid (GMP)
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11-cis-Retinoic Acid-d5
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Retinoic acid-d6
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Retinoic acid purchased from MedChemExpress. Usage Cited in:
Oncotarget. 2017 Nov 22;8(65):109135-109150.
[Abstract]
Cell morphology of MCF-7 treated with RA (20 μM)+ω-3 PUFAs (80 μM) with or without 3-MA (5 mM) for 24h.
Retinoic acid purchased from MedChemExpress. Usage Cited in:
Oncotarget. 2017 Nov 22;8(65):109135-109150.
[Abstract]
Cells are treated with RA (20 μM) plus ω-3 PUFAs (80 μM) with or without CQ (5 μM) for 24 h. Cell extracts are prepared and subjected to western blotting analysis.
Retinoic acid purchased from MedChemExpress. Usage Cited in:
Oncotarget. 2017 Nov 22;8(65):109135-109150.
[Abstract]
MCF-7 cells are pretreated with the indicated chemical inhibitors for 30min, followed by 15 min treatment with RA (20 μM) + EPA (80 μM).Cell extracts are prepared and subjected to western blotting analysis.
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Description
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.
IC50 & Target[2][5]
PPARβ/δ
17 nM (Kd)
PPARα
103 nM (Kd)
PPARγ
178 nM (Kd)
Human Endogenous Metabolite
PPARα
14 nM (IC50)
PPARγ
14 nM (IC50)
RARβ
14 nM (IC50)
In Vitro
Retinoic acid (All-trans-retinoic acid, ATRA) is a highly potent derivative of vitamin A that is required for virtually all essential physiological processes and functions because of its involvement in transcriptional regulation of over 530 different genes. Retinoic acid exerts its actions by serving as an activating ligand of nuclear retinoic acid receptors (RARα-γ), which form heterodimers with retinoid X receptors (RXRα-γ)[1]. Retinoic acid (RA) bound to PPARα and PPARγ with a low affinity demonstrated by Kd values of 100-200 nM. In contrast, Retinoic acid associates with PPARβ/δ with a Kd of 17 nM, revealing both high affinity and isotype selectivity[2].Undifferentiated P19 cells express the Retinoic acid (RA) receptors RARα, RARβ, RARγ, and PPARβ/δ, as well as the Retinoic acid -binding proteins CRABP-II and FABP5. Induction of differentiation by treatment of cells with Retinoic acid results in transient up-regulation of CRABP-II and down-regulation of FABP5 that are observed at the level of both the respective proteins and mRNAs. Following the initial decrease, the level of both FABP5 protein and mRNA increases to attain a 2-2.5-fold higher level in mature neurons as compared with undifferentiated P19 cells. Induction of differentiation does not markedly affect the levels of either RARα or PPARβ/δ. The level of RARγ mRNA decreases by about 5-fold by day 4 and remained low in mature neurons[3].Retinoic acid (RA) is a morphogen derived from retinol (vitamin A) that plays important roles in cell growth, differentiation, and organogenesis. The Retinoic acid interacts with retinoic acid receptor (RAR) and retinoic acid X receptor (RXR) which then regulate the target gene expression[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Retinoic acid Related Antibodies
Essai clinique
Masse moléculaire
300.44
Formule
C20H28O2
CAS No.
302-79-4
Appearance
Solid
Color
Light yellow to yellow
SMILES
CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C(O)=O)=C(C)CCC1
Structure Classification
Ketones, Aldehydes, Acids
Initial Source
Microorganisms
Endogenous metabolite
Livraison
Room temperature in continental US; may vary elsewhere.
Stockage
-20°C, sealed storage, away from moisture and light
*In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)
Solvant et solubilité
In Vitro:
DMSO : 50 mg/mL (166.42 mM; ultrasonic and warming and heat to 60°C; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Preparing Stock Solutions
ConcentrationSolventMass
1 mg
5 mg
10 mg
1 mM
3.3285 mL
16.6423 mL
33.2845 mL
5 mM
0.6657 mL
3.3285 mL
6.6569 mL
10 mM
0.3328 mL
1.6642 mL
3.3285 mL
View the Complete Stock Solution Preparation Table
*Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles. Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day. The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Protocol 1
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: 2.5 mg/mL (8.32 mM); Suspended solution; Need ultrasonic and warming
This protocol yields a suspended solution of 2.5 mg/mL. Suspended solution can be used for oral and intraperitoneal injection.
Taking 1 mL working solution as an example, add 100 μLDMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Protocol 2
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
This protocol yields a suspended solution of ≥ 2.5 mg/mL (saturation unknown). Suspended solution can be used for oral and intraperitoneal injection.
Taking 1 mL working solution as an example, add 100 μLDMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
Protocol 3
Add each solvent one by one: 10% DMSO 90% Corn Oil
Solubility: ≥ 2.5 mg/mL (8.32 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Taking 1 mL working solution as an example, add 100 μLDMSO stock solution (25.0 mg/mL) to 900 μLCorn oil, and mix evenly.
Protocol 4
Add each solvent one by one: 5% DMSO 40% PEG300 5% Tween-80 50% Saline
Solubility: 2.5 mg/mL (8.32 mM); Suspended solution; Need ultrasonic
Protocol 5
Add each solvent one by one: 5% DMSO 95% (20% SBE-β-CD in Saline)
Solubility: 2.5 mg/mL (8.32 mM); Suspended solution; Need ultrasonic
For the following dissolution methods, please prepare the working solution directly.
It is recommended to prepare fresh solutions and use them promptly within a short period of time. The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution.
If precipitation or phase separation occurs during preparation,
heat and/or sonication can be used to aid dissolution.
Protocol 1
Add each solvent one by one: 50% PEG300 50% PBS
Solubility: 5 mg/mL (16.64 mM); Suspended solution; Need ultrasonic and warming and heat to 40°C
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:
Dosage
mg/kg
Animal weight (per animal)
g
Dosing volume (per animal)
μL
Number of animals
Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
%
DMSO+
%
+
%
Tween-80
+
%
Saline
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
The co-solvents required include: DMSO,
. All of co-solvents are available by MedChemExpress (MCE).
, Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Calculation results:
Working solution concentration:
mg/mL
Method for preparing stock solution:
mg
drug dissolved in
μL
DMSO (Stock solution concentration: mg/mL).
*In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light)
The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
Method for preparing in vivo working solution for animal experiments: Take
μL DMSO stock solution, add
μL .
μL , mix evenly, next add
μL Tween 80, mix evenly, then add
μL Saline.
Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution
If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
[1]. 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.
[Content Brief]
[2]. 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.
[Content Brief]
[3]. 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.
[Content Brief]
[4]. Kam RK, et al. Retinoic acid synthesis and functions in early embryonic development. Cell Biosci. 2012 Mar 22;2(1):11.
[Content Brief]
[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.
[Content Brief]
[6]. 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.
[Content Brief]
Test cellulaire
[3]
P19 cell are induced to undergo neuronal differentiation according to established procedures. Briefly, cells are cultured on 1% agarose-coated 10 cm dishes at 3×10 5 cells/mL in α-minimal essential medium supplemented with 10% FBS. Differentiation is induced by addition of Retinoic acid (1 μM) and medium containing Retinoic acid replaced 2 days later. On day 4, cell aggregates are collected by centrifugation, separated to single cells by trypsin/EDTA treatment, replated onto poly-L-lysine-coated plates, and cultured in α-minimal essential medium supplemented with 10% FBS. On day 6, medium is replaced with neurobasal medium containing B27 supplement and 2 mM GlutaMAX. Medium is replaced every 2 days for an additional week[3].
MCE n'a pas confirmé de manière indépendante l'exactitude de ces méthodes. Ils sont pour référence seulement.
Références
[1]. 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.
[Content Brief]
[2]. 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.
[Content Brief]
[3]. 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.
[Content Brief]
[4]. Kam RK, et al. Retinoic acid synthesis and functions in early embryonic development. Cell Biosci. 2012 Mar 22;2(1):11.
[Content Brief]
[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.
[Content Brief]
[6]. 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.
[Content Brief]
[1]. 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.
[2]. 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.
[3]. 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.
[4]. Kam RK, et al. Retinoic acid synthesis and functions in early embryonic development. Cell Biosci. 2012 Mar 22;2(1):11.
[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]. 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.
Complete Stock Solution Preparation Table
*Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles. Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture and light). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Optional Solvent
ConcentrationSolventMass
1 mg
5 mg
10 mg
25 mg
DMSO
1 mM
3.3285 mL
16.6423 mL
33.2845 mL
83.2113 mL
5 mM
0.6657 mL
3.3285 mL
6.6569 mL
16.6423 mL
10 mM
0.3328 mL
1.6642 mL
3.3285 mL
8.3211 mL
15 mM
0.2219 mL
1.1095 mL
2.2190 mL
5.5474 mL
20 mM
0.1664 mL
0.8321 mL
1.6642 mL
4.1606 mL
25 mM
0.1331 mL
0.6657 mL
1.3314 mL
3.3285 mL
30 mM
0.1109 mL
0.5547 mL
1.1095 mL
2.7737 mL
40 mM
0.0832 mL
0.4161 mL
0.8321 mL
2.0803 mL
50 mM
0.0666 mL
0.3328 mL
0.6657 mL
1.6642 mL
60 mM
0.0555 mL
0.2774 mL
0.5547 mL
1.3869 mL
80 mM
0.0416 mL
0.2080 mL
0.4161 mL
1.0401 mL
100 mM
0.0333 mL
0.1664 mL
0.3328 mL
0.8321 mL
Retinoic acid Related Classifications
Stem Cell/WntMetabolic Enzyme/ProteaseVitamin D Related/Nuclear ReceptorCell Cycle/DNA DamageAutophagy
OrganoidRAR/RXRPPAREndogenous MetaboliteAutophagy
Help & FAQs
Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.
Keywords:
Retinoic acid302-79-4Vitamin A acid all-trans-Retinoic acid ATRAOrganoidRAR/RXRPPAREndogenous MetaboliteAutophagyRetinoic acid receptorsRetinoid X receptorsPeroxisome proliferator-activated receptorsInhibitorinhibitorinhibit
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