Stemolecule™ ec23

ec23 is a pan-RAR receptor agonist that is stable and maintains the same biological activity as ATRA (all trans retinoic acid). ATRA is well known for its ability to regulate cell differentiation. However, retinoids such as ATRA are excellent chromophores and efficiently absorb light and isomerise. This is not a desirable property for cell culture reagents where consistency and reliability of a molecule is important for robust, reproducible results.

REPROCELL routinely test the stability of the our synthetic compounds in line with their development as stable alternatives to known biological molecules. The structural stability of ec23 and ATRA were examined by NMR during prolonged exposure to light. ATRA shows significant isomerisation and degradation whereas ec23 remains completely intact.

Robust induction of neurogenesis by ec23

The synthetic retinoid, ec23 is a potent inducer of pluripotent stem cell differentiation. Human TERA2.cl.SP12 pluripotent stem cells exposed to either 10 uM ec23 or ATRA form populations of terminally differentiated neurons. Immunocytochemical staining for neurofilament-200 was performed on differentiated cultures and the number of positive cells quantified. Results show that ec23 is a more potent inducer of neurogenesis than ATRA. In direct comparison to ATRA, synthetic retinoid ec23 induces larger numbers of neural cells with less variability and with the added advantage of compound stability.

Synthetic retinoid ec23 is also a potent inducer of neurogenesis by adult neuroprogenitor cells. Rat adult hippocampal progenitor cells (AHPCs) exposed to either 1 uM ec23 or ATRA differentiate into neural cell types. Differentiation induced by exposure to ec23 was consistent and reproducible.

Human TERA2.cl.SP12 EC cells exposed to either ec23 or ATRA form populations of terminally differentiated neurons after 21 days. Immunocytochemical staining for neurofilament-200 was performed on differentiated cultures.

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Stemgent and the Stemolecule brand name are trademarks of REPROCELL Inc., Japan.

Product Name: Stemolecule ec23

Catalog Number: SRP002

Size:

• 5 mg (SRP002)
• 2 × 5 mg (SRP002-2)

Alternate Name(s): 4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylethynyl) benzoic acid

Chemical Formula: C₂₃H₂₄O₂

Molecular Weight: 332 g/mol

CAS Number: 104561-41-3

Purity: Greater than 99% by HPLC analysis

Formulation: Off-white solid

Solubility: Reconstitute in DMSO to the desired concentration. For reconstitution instructions please reference product specifications sheet.

Storage and Stability: Store powder at ≤20 °C. Following reconstitution, store in aliquots at −20 °C. Stock solutions are stable for 6 months when stored as directed.

Quality Control: The purity of ec23 was determined by HPLC analysis. The accurate mass was determined by mass spectrometry.

Safety Data Sheets:

• SR-P002 and SR-P002-2 SDS

1. Christie VB; Barnard JH; Batsanov AS; Bridgens CE; Cartmell EB; Collings JC; Maltman DJ; Redfern CPF; Marder TB; Przyborski S; Whiting A. Synthesis and evaluation of synthetic retinoid derivatives as inducers of stem cell differentiation. Org Biomol Chem 6: 3497 (2008).

Additional Publications

• Goncalves KE; Phillips S; Shah DSH; Athey D; Przyborski S. Application of biomimetic surfaces and 3D culture technology to study the role of extracellular matrix interactions in neurite outgrowth and inhibition. Biomaterials Advances 144:213204 (2022).
• Tan SM; Altschuler G; Zhao TY; Ang HS; Yang H; Lim B; Vardy L; Hide W; Thomson AM; Lareu RR. Divergent LIN28-mRNA associations result in translational suppression upon the initiation of differentiation. Nucl Acids Res 42: 7997 (2014).
• Clemens G; Flower KR; Henderson AP; Whiting A; Przyborski SA; Jimenez-Hernandez M; Ball F; Basssan P; Cinque G; Gardner P. The action of all-trans-retinoic acid (ATRA) and synthetic retinoid analogues (EC19 and EC23) on human pluripotent stem cells differentiation investigated using single cell infrared microspectroscopy. Mol Biol Syst 9: 699 (2013).