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Application of thin layer and column chromatography in monitoring the synthesis of α- tocopheryl-lysine ester

Primena metoda tankoslojne hromatografije i hromatografije na koloni u praćenju sinteze α-tokoferil-lizin estra

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2014
2276.pdf (369.9Kb)
Authors
Gagić, Žarko
Ivković, Branka
Nikolić, Katarina
Agbaba, Danica
Article (Published version)
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Abstract
Vitamin E comprises of two families of compounds, tocopherols and tocotrienols. It is well known for its antioxidant activity, but recently special attention is paid to the use of vitamin E and its derivatives in the prevention and the treatment of cancer. Various derivatives of vitamin E are synthesized, which exhibit antiproliferative activity. It has been shown that the α-tocopherol ester with the amino acid lysine exhibits improved antiproliferative activity on MCF-7 breast cancer cell line as compared to commercially available preparations. The first stage was the synthesis of α-tocopherol ester with di-Cbz-lysine. Synthesis of ester was monitored by thin layer chromatography (mobile phase: n-hexane-ethyl acetate 3: 1,2 v/v) and the purification of product was done by dry flash column chromatography and by preparative plate chromatography (mobile phase: n-hexane-ethyl acetate 3: 1,2 v/v). In the second stage, Cbz protecting groups were removed by catalytic hydrogenation. The final... product α- tocopheryl-lysine ester was detected by TLC (mobile phase: dichloromethane-methanolammonia 9 : 0,9 : 0,1 v/v).

Vitamin E sačinjavaju dve klase jedinjenja, tokoferoli i tokotrienoli. Dobro je poznata njegova antioksidativna aktivnost, a danas se posebna pažnja obraća na upotrebu vitamina E i njegovih derivata u prevenciji i terapiji kancera. Sintetisani su brojni derivati vitamina E koji ispoljavaju antiproliferativnu aktivnost. Pokazano je da estar α-tokoferola sa aminokiselinom lizinom ispoljava bolju antiproliferativnu aktivnost na MCF-7 ćelijskoj liniji karcinoma dojke u odnosu na komercijalno dostupne preparate. U prvoj fazi sintetisan je estar α-tokoferola sa di- Cbz-lizinom. Tok sinteze estra praćen je metodom tankoslojne hromatografije (mobilna faza: nheksan/ etilacetat 3: 1,2 v/v), dok je prečišćavanje proizvoda izvršeno dry flash hromatografijom i preparativnom hromatografijom na ploči (mobilna faza: n-heksan -etil acetat 3: 1,2 v/v). U drugoj fazi katalitičkom hidrogenacijom uklonjene su zaštitne Cbz-grupe sa amino grupa lizina. Finalni proizvod α-tokoferil lizin estar detektovan je p...rimenom TLC metode (mobilna faza: dihlormetan-metanol-amonijak 9 : 0,9 : 0,1 v/v/v).

Keywords:
α-tocopherol / antiproliferative activity / MCF-7 / thin layer chromatography / dry flash chromatography / α-tokoferol / antiproliferativna aktivnost / MCF-7 / tankoslojna hromatografija / dry flash hromatografija
Source:
Arhiv za farmaciju, 2014, 64, 3, 261-270
Publisher:
  • Savez farmaceutskih udruženja Srbije, Beograd

DOI: 10.5937/arhfarm1403261G

ISSN: 0004-1963

Scopus: 2-s2.0-84943763872
[ Google Scholar ]
URI
https://farfar.pharmacy.bg.ac.rs/handle/123456789/2278
Collections
  • Radovi istraživača / Researchers’ publications
Institution/Community
Pharmacy
TY  - JOUR
AU  - Gagić, Žarko
AU  - Ivković, Branka
AU  - Nikolić, Katarina
AU  - Agbaba, Danica
PY  - 2014
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2278
AB  - Vitamin E comprises of two families of compounds, tocopherols and tocotrienols. It is well known for its antioxidant activity, but recently special attention is paid to the use of vitamin E and its derivatives in the prevention and the treatment of cancer. Various derivatives of vitamin E are synthesized, which exhibit antiproliferative activity. It has been shown that the α-tocopherol ester with the amino acid lysine exhibits improved antiproliferative activity on MCF-7 breast cancer cell line as compared to commercially available preparations. The first stage was the synthesis of α-tocopherol ester with di-Cbz-lysine. Synthesis of ester was monitored by thin layer chromatography (mobile phase: n-hexane-ethyl acetate 3: 1,2 v/v) and the purification of product was done by dry flash column chromatography and by preparative plate chromatography (mobile phase: n-hexane-ethyl acetate 3: 1,2 v/v). In the second stage, Cbz protecting groups were removed by catalytic hydrogenation. The final product α- tocopheryl-lysine ester was detected by TLC (mobile phase: dichloromethane-methanolammonia 9 : 0,9 : 0,1 v/v).
AB  - Vitamin E sačinjavaju dve klase jedinjenja, tokoferoli i tokotrienoli. Dobro je poznata njegova antioksidativna aktivnost, a danas se posebna pažnja obraća na upotrebu vitamina E i njegovih derivata u prevenciji i terapiji kancera. Sintetisani su brojni derivati vitamina E koji ispoljavaju antiproliferativnu aktivnost. Pokazano je da estar α-tokoferola sa aminokiselinom lizinom ispoljava bolju antiproliferativnu aktivnost na MCF-7 ćelijskoj liniji karcinoma dojke u odnosu na komercijalno dostupne preparate. U prvoj fazi sintetisan je estar α-tokoferola sa di- Cbz-lizinom. Tok sinteze estra praćen je metodom tankoslojne hromatografije (mobilna faza: nheksan/ etilacetat 3: 1,2 v/v), dok je prečišćavanje proizvoda izvršeno dry flash hromatografijom i preparativnom hromatografijom na ploči (mobilna faza: n-heksan -etil acetat 3: 1,2 v/v). U drugoj fazi katalitičkom hidrogenacijom uklonjene su zaštitne Cbz-grupe sa amino grupa lizina. Finalni proizvod α-tokoferil lizin estar detektovan je primenom TLC metode (mobilna faza: dihlormetan-metanol-amonijak 9 : 0,9 : 0,1 v/v/v).
PB  - Savez farmaceutskih udruženja Srbije, Beograd
T2  - Arhiv za farmaciju
T1  - Application of thin layer and column chromatography in monitoring the synthesis of α- tocopheryl-lysine ester
T1  - Primena metoda tankoslojne hromatografije i hromatografije na koloni u praćenju sinteze α-tokoferil-lizin estra
VL  - 64
IS  - 3
SP  - 261
EP  - 270
DO  - 10.5937/arhfarm1403261G
UR  - conv_523
ER  - 
@article{
author = "Gagić, Žarko and Ivković, Branka and Nikolić, Katarina and Agbaba, Danica",
year = "2014",
abstract = "Vitamin E comprises of two families of compounds, tocopherols and tocotrienols. It is well known for its antioxidant activity, but recently special attention is paid to the use of vitamin E and its derivatives in the prevention and the treatment of cancer. Various derivatives of vitamin E are synthesized, which exhibit antiproliferative activity. It has been shown that the α-tocopherol ester with the amino acid lysine exhibits improved antiproliferative activity on MCF-7 breast cancer cell line as compared to commercially available preparations. The first stage was the synthesis of α-tocopherol ester with di-Cbz-lysine. Synthesis of ester was monitored by thin layer chromatography (mobile phase: n-hexane-ethyl acetate 3: 1,2 v/v) and the purification of product was done by dry flash column chromatography and by preparative plate chromatography (mobile phase: n-hexane-ethyl acetate 3: 1,2 v/v). In the second stage, Cbz protecting groups were removed by catalytic hydrogenation. The final product α- tocopheryl-lysine ester was detected by TLC (mobile phase: dichloromethane-methanolammonia 9 : 0,9 : 0,1 v/v)., Vitamin E sačinjavaju dve klase jedinjenja, tokoferoli i tokotrienoli. Dobro je poznata njegova antioksidativna aktivnost, a danas se posebna pažnja obraća na upotrebu vitamina E i njegovih derivata u prevenciji i terapiji kancera. Sintetisani su brojni derivati vitamina E koji ispoljavaju antiproliferativnu aktivnost. Pokazano je da estar α-tokoferola sa aminokiselinom lizinom ispoljava bolju antiproliferativnu aktivnost na MCF-7 ćelijskoj liniji karcinoma dojke u odnosu na komercijalno dostupne preparate. U prvoj fazi sintetisan je estar α-tokoferola sa di- Cbz-lizinom. Tok sinteze estra praćen je metodom tankoslojne hromatografije (mobilna faza: nheksan/ etilacetat 3: 1,2 v/v), dok je prečišćavanje proizvoda izvršeno dry flash hromatografijom i preparativnom hromatografijom na ploči (mobilna faza: n-heksan -etil acetat 3: 1,2 v/v). U drugoj fazi katalitičkom hidrogenacijom uklonjene su zaštitne Cbz-grupe sa amino grupa lizina. Finalni proizvod α-tokoferil lizin estar detektovan je primenom TLC metode (mobilna faza: dihlormetan-metanol-amonijak 9 : 0,9 : 0,1 v/v/v).",
publisher = "Savez farmaceutskih udruženja Srbije, Beograd",
journal = "Arhiv za farmaciju",
title = "Application of thin layer and column chromatography in monitoring the synthesis of α- tocopheryl-lysine ester, Primena metoda tankoslojne hromatografije i hromatografije na koloni u praćenju sinteze α-tokoferil-lizin estra",
volume = "64",
number = "3",
pages = "261-270",
doi = "10.5937/arhfarm1403261G",
url = "conv_523"
}
Gagić, Ž., Ivković, B., Nikolić, K.,& Agbaba, D.. (2014). Application of thin layer and column chromatography in monitoring the synthesis of α- tocopheryl-lysine ester. in Arhiv za farmaciju
Savez farmaceutskih udruženja Srbije, Beograd., 64(3), 261-270.
https://doi.org/10.5937/arhfarm1403261G
conv_523
Gagić Ž, Ivković B, Nikolić K, Agbaba D. Application of thin layer and column chromatography in monitoring the synthesis of α- tocopheryl-lysine ester. in Arhiv za farmaciju. 2014;64(3):261-270.
doi:10.5937/arhfarm1403261G
conv_523 .
Gagić, Žarko, Ivković, Branka, Nikolić, Katarina, Agbaba, Danica, "Application of thin layer and column chromatography in monitoring the synthesis of α- tocopheryl-lysine ester" in Arhiv za farmaciju, 64, no. 3 (2014):261-270,
https://doi.org/10.5937/arhfarm1403261G .,
conv_523 .

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