α-(+)-Tocopherol (Vitamin E) Amidite
ChemGenes Introduces High Purity α-(+)-Tocopherol (Vitamin E) Amidite
ChemGenes Corporation is now offering ultra pure α-(+)-Tocopherol amidites for attaching it to oligonucleotides for applications such as delivery and cellular uptake.
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α-(+)-Tocopherol; CLP-2706
Tocopherol is not produced by the target cells, but is essential for the target cells; hence it serves as an effective in vivo carrier.
α-Tocopherol is a lipophilic natural molecule and has physiological pathways from blood to the brain as well as
to the liver. As with cholesterol modifications, α-Tocopherol has been shown to have potential use in the delivery
of oligonucleotides into cells.
a. b..
Analytical data of the (+)-α-Tocopherol Amidite; a. 31P NMR >98% and b. HPLC >98% purity.
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α-(+)-Tocopherol (Vitamin E) Amidite
α-(+)-Tocopherol (Vitamin E)
Key Features and Applications:
• Studies in humans has shown that, Vitamin E is essentially non-toxic and causes no side effect even at very
high doses.
• Further it has been shown in animal experiments that Vitamin E has neither mutagenic, teratogenic nor
carcinogenic properties.
• Tocopherol has hydrophobic nature and is transported in plasma lipoproteins. The pathways involved in its
cellular uptake are closely related to the lipoprotein metabolism.
• Tocopherol is found mainly in association with membranes of sub-cellular organelle, such as the endoplasmic reticulum and mitochondria, rather than in the plasma membrane. This maximizes the possibility of
intracellular transport.
• It is known that α-Tocopherol interacts with serum proteins, and these proteins might play a role in the conjugate uptake.
• α-Tocopherol (Vitamin E) has been successfully utilized as a carrier molecule of siRNA in vivo to the liver and
brain.
• In membranes, the phytyl side chain of the Vitamin E is embedded in the membrane, with the phenolic
hydroxyl group towards the surface. Thus attachment of the oligonucleotide to the phenolic hydroxyl group
should have a minimal effect on the interactions of the Vitamin E with membranes.
• The hydrophobic nature of Tocopherol has also been utilized as a means of improving the purification of
ribozymes.
Importent Note: α-(+)-Tocopherol modification can be conveniently incorporated at the 3’-end using the reverse RNA
technology developed by ChemGenes Corporation.
References:
1. Kappus, H.; Diplock, A. T. Free Radic. Biol. Med. 1992, 13, 55.
2. Will, D. W.; Brown, T. Tet. Lett. 1992, 2729.
3. Nihina, K.; Unno, T.; Uno, Y.; Kubodera, T.; Kanouchi, T.; Mizusawa, H.; Yokota, T. Mol. Ther., 2008, 16, 734.
4. Sproat, B. S.; Rupp, T.; Menhardt, N.; Keane, D.; Beijer, B. Nucleic Acids Res. 27, 1999, 1950.
5. Rigotti, A. Mol. Asp. Med. 2007, 28, 423.
For a complete product listing, visit us at www.chemgenes.com
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