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
Апстракт
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).
Кључне речи:
α-tocopherol / antiproliferative activity / MCF-7 / thin layer chromatography / dry flash chromatography / α-tokoferol / antiproliferativna aktivnost / MCF-7 / tankoslojna hromatografija / dry flash hromatografijaИзвор:
Arhiv za farmaciju, 2014, 64, 3, 261-270Издавач:
- Savez farmaceutskih udruženja Srbije, Beograd
Институција/група
PharmacyTY - 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 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" }
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
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 .
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 . .