α-Tocopherol pro-vitamins:: synthesis, hydrolysis and accumulation in rabbit ear skin
α-Tocopherol pro-vitamins:: synthesis, hydrolysis and accumulation in rabbit ear skin
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DOI：
10.1016/j.jconrel.2004.08.002
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发表时间：
2004-10-19
影响因子：
10.8
通讯作者：
Santi, P
中科院分区：
文献类型：
--
作者：
Ostacolo, C;Marra, F;Santi, P
我们合成了α -tocoplierol （VE）酯，目的是开发新的前维生素，容易被皮肤中的酶重新转化，并能够释放另一种活性部分，如氨基酸，以获得协同效应。特别注意的是氨基酸甘氨酸、丙氨酸和焦谷氨酸。采用猪肝酯酶对维生素原的酶解敏感性进行了体外评价。采用兔耳皮肤进行渗透实验，定量测定表皮和真皮层中原维生素和衍生性VE的含量。合成的新衍生物，特别是甘氨酸和丙氨酸衍生物，在兔皮肤中大量积累，并产生大量的a-生育酚。与醋酸酯衍生物（VEAc）相比，累积的量相当或更高。此外，新的衍生物，更亲水，允许使用载体，如混合物水/丙二醇/乙醇广泛用于乳霜和凝胶的制备。最后，这些新衍生物的酶代谢不仅产生VE，而且还产生对皮肤有进一步有利作用的成分。(C) 2004 Elsevier B.V.版权所有
We synthesized esters of alpha-tocoplierol (VE) with the aim to develop new pro-vitamins, easily reconverted by enzymes in the skin and able to release another active moiety such as an amino acid, in order to obtain a synergic effect. In particular, the attention was dedicated to the amino acids glycine and alanine and to pyroglutamic acid. The sensitivity of pro-vitamins to enzymatic hydrolysis was evaluated in vitro using porcine liver esterase. Permeation experiments were performed using rabbit ear skin, for the quantification of pro-vitamins and derived VE in the epidermis and dermis. The new derivatives synthesized, and in particular the glycine and alanine derivatives, accumulated in rabbit skin in a significant extent and originated substantial amounts of a-tocopherol. In comparison with the acetate derivative (VEAc), the amounts accumulated are comparable or higher. Moreover, the new derivatives, being more hydrophilic, allow the use of vehicles such as the mixture water/propylene glycol/ethanol widely employed for the preparation of creams and gels. Finally, the enzymatic metabolism of these new derivatives generates not only VE, but also components that can have a further advantageous action on skin. (C) 2004 Elsevier B.V. All rights reserved.