Stemolecule™ All-Trans Retinoic Acid

Stemolecule™ All-Trans Retinoic Acid

Stemolecule™ All-Trans Retinoic Acid is the oxidized form of Vitamin A and functions as a signaling molecule for various developmental pathways that control differentiation¹ and proliferation². It acts by binding to heterodimers of the retinoic acid receptor (RAR) and the retinoid X receptor (RXR), which then bind to retinoic acid response elements (RAREs) in the regulatory regions activating gene transcription³. All-Trans Retinoic Acid has been implicated in specification of the embryonic anterior/posterior axis through Hox gene regulation⁴. It has been used in various differentiation protocols, including B-cells², T cells⁵ and neurons^6-9, and applied clinically to treat cancer as a form of differentiation-induction therapy^10,11.

References

1. Duester, G. (2008) Retinoic acid synthesis and signaling during early organogenesis. Cell 134: 921-31.
2. Ertesvag, A., Naderi, S., Blomhoff, H.K. (2009) Regulation of B cell proliferation and differentiation by retinoic acid. Semin Immunol 21: 36-41.
3. Marshall, H., Morrison, A., Studer, M., Popperl, H., Krumlauf, R. (1996) Retinoids and Hox genes. FASEB J 10: 969-78.
4. Holland, L.Z. (2007) Developmental biology: a chordate with a difference. Nature 447: 153-5.
5. Yagi, J., Uchida, T., Kuroda, K., Uchiyama, T. (1997) Influence of retinoic acid on the differentiation pathway of T cells in the thymus. Cell Immunol 181: 153-62.
6. Dhara, S.K., Stice, S.L. (2008) Neural differentiation of human embryonic stem cells. J Cell Biochem 105: 633-40.
7. Sasai, Y. (2002) Generation of dopaminergic neurons from embryonic stem cells. J Neurol 249 Suppl 2: II41-4.
8. Takahashi, J., Palmer, T.D., Gage, F.H. (1999) Retinoic acid and neurotrophins collaborate to regulate neurogenesis in adult-derived neural stem cell cultures. J Neurobiol 38: 65-81.
9. Wichterle, H., Lieberam, I., Porter, J.A., Jessell, T.M. (2002) Directed differentiation of embryonic stem cells into motor neurons. Cell 110: 385-97.
10. Collins, S.J. (2008) Retinoic acid receptors, hematopoiesis and leukemogenesis. Curr Opin Hematol 15: 346-51.
11. Mongan, N.P., Gudas, L.J. (2007) Diverse actions of retinoid receptors in cancer prevention and treatment. Differentiation 75: 853-70.

For research use only. Not for use in diagnostic procedures. Not for resale.

Stemolecule™ All-Trans Retinoic Acid

Alternate Names	Tretinoin, Vitamin A Acid, Airol, Trans-Retinoic acid, Dermairol, Aknoten, Aberel, Eudyna, Vesanoid, 2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
Chemical Formula	C20H28O2
Structure
Molecular Weight	300.44
CAS Number	302-79-4
Purity	>98%
Formulation	Yellow to light orange crystalline powder
Solubility	Soluble in DMSO (100 mM) or 95% ethanol (9 mM). For a 10 mM concentrated stock solution, reconstitute the compound by adding 1664 µl of DMSO to the entire contents of the vial. Note: for most cells, the maximum tolerance to DMSO is <0.5%.
Storage	Store at 4°C. Protect from light. Following reconstitution, store aliquots at -20°C.
Stability	Stock solutions stable at -20°C for 6 months.
Quality control	The purity of All-Trans Retinoic Acid was determined by HPLC analysis. The accurate mass and structure of All-Trans Retinoic Acid was determined by mass spectrometry and NMR, respectively. Cellular toxicity of All-Trans Retinoic Acid was tested on mouse embryonic stem cells.
References	Duester, G. (2008) Retinoic acid synthesis and signaling during early organogenesis. Cell 134: 921-31. Ertesvag, A., Naderi, S., Blomhoff, H.K. (2009) Regulation of B cell proliferation and differentiation by retinoic acid. Semin Immunol 21: 36-41. Marshall, H., Morrison, A., Studer, M., Popperl, H., Krumlauf, R. (1996) Retinoids and Hox genes. FASEB J 10: 969-78. Holland, L.Z. (2007) Developmental biology: a chordate with a difference. Nature 447: 153-5. Yagi, J., Uchida, T., Kuroda, K., Uchiyama, T. (1997) Influence of retinoic acid on the differentiation pathway of T cells in the thymus. Cell Immunol 181: 153-62. Dhara, S.K., Stice, S.L. (2008) Neural differentiation of human embryonic stem cells. J Cell Biochem 105: 633-40. Sasai, Y. (2002) Generation of dopaminergic neurons from embryonic stem cells. J Neurol 249 Suppl 2: II41-4. Takahashi, J., Palmer, T.D., Gage, F.H. (1999) Retinoic acid and neurotrophins collaborate to regulate neurogenesis in adult-derived neural stem cell cultures. J Neurobiol 38: 65-81. Wichterle, H., Lieberam, I., Porter, J.A., Jessell, T.M. (2002) Directed differentiation of embryonic stem cells into motor neurons. Cell 110: 385-97. Collins, S.J. (2008) Retinoic acid receptors, hematopoiesis and leukemogenesis. Curr Opin Hematol 15: 346-51. Mongan, N.P., Gudas, L.J. (2007) Diverse actions of retinoid receptors in cancer prevention and treatment. Differentiation 75: 853-70.

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