Synthesis and antioxidant activity of new homocarnosine β-cyclodextrin conjugates
Synthesis and antioxidant activity of new homocarnosine β-cyclodextrin conjugates
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DOI：
10.1016/j.ejmech.2006.12.036
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发表时间：
2007-07-01
影响因子：
6.7
通讯作者：
Vecchio, Graziella
中科院分区：
文献类型：
--
作者：
Amorini, Angela Maria;Bellia, Francesco;Vecchio, Graziella
几项体外和体内研究表明，肌肽（β-丙氨酰-L-组氨酸）和高肌苷（β-氨基丁酰-L-组氨酸）可以作为活性氧的清除剂。β-环糊精用高肌苷官能化，获得以下新的生物缀合物异构体：6（A）-[（4-1[（IS）-1-羧基-2-甲基-IH-吡唑-4-基）氨基]-2-氧代-IH-吡唑-4-基]-2-甲基-IH-吡唑-4-甲酰胺（1H-咪唑-4-基）乙基]氨基}-4-氧代丁基）氨基]-6（A）-脱氧-O-环糊精和（2（A）S，3（A）R）-3（A）+4-{ [（1 S）-1-羧基-2-（1H-咪唑-4-基）乙基]氨基}-4-氧代丁基）氨基]-3（A）-脱氧-β-环糊精。脉冲辐解研究表明，β-环糊精高卡霉素生物缀合物是（OH）-O-中心点自由基的清除剂，这是由于形成了稳定的咪唑中心自由基和大环葡萄糖分子的清除能力。这些新的β-环糊精衍生物抑制铜（II）驱动的LDL氧化的能力进行了测定，与类似的camosine衍生物所显示的比较。这两种β-环糊精肌肽异构体显示出更高的保护效果比游离二肽和homocarnosine衍生物，使光的β-CD cavity. The的作用，这些新的β-环糊精衍生物抑制铜（II）驱动的LDL氧化的能力进行了测定，与所显示的类似肌肽衍生物相比。这两种β-环糊精肌肽异构体都显示出比游离二肽和高肌苷衍生物更高的保护作用，从而揭示了O-CD腔的作用。(c)2007年Elsevier Masson SAS。All rights reserved.
Several in vitro and in vivo studies have suggested that carnosine (beta-alanil-L-histidine) and homocamosine (beta-aminobutyril-L-histidine) can act as scavengers of reactive oxygen species. beta-Cyclodextrin was functionalized with homocamosine, obtaining the following new bioconjugate isomers: 6(A)-[(4-1[(IS)-1-carboxy-2-(1H-imidazol-4-yl)ethyl] amino}-4-oxobutyl)amino]-6(A)-deoxy-o-cyclodextrin and (2(A)S,3(A)R)-3(A)+4-{ [(1S)-1-carboxy-2-(1H-imidazol-4-yl)ethyl] amino}-4-oxobutyl)amino]-3(A)-deoxy-beta-cyclodextrin. Pulse radiolysis investigations show that the beta-cyclodextrin homocamosine bioconjugates are scavengers of (OH)-O-center dot radicals because of the formation of stable imidazole-centered radicals and the scavenger ability of glucose molecules of the macrocycle. The ability of these new beta-cyclodextrin derivatives to inhibit the copper(II) driven LDL oxidation was determined in comparison with that displayed by the analogous camosine derivatives. Both the beta-cyclodextrin carnosine isomers show a higher protective effect than that of free dipeptide and homocarnosine derivatives, bringing into light the role of the beta-CD cavity.The ability of these new beta-cyclodextrin derivatives to inhibit the copper(II) driven LDL oxidation was determined in comparison with that displayed by the analogous carnosine derivatives. Both the beta-cyclodextrin carnosine isomers show a higher protective effect than that of free dipeptide and homocamosine derivatives, bringing into light the role of the O-CD cavity. (c) 2007 Elsevier Masson SAS. All rights reserved.