摘要
目的合成一系列脂酰苯丙氨酸凝胶因子——肉豆蔻酰-苯丙氨酸甲酯（C14-L-Phe-OMe）、棕榈酰-苯丙氨酸甲酯（C16-L-Phe-OMe）及硬脂酰-苯丙氨酸甲酯（C18-L-Phe-OMe）,并对其进行结构表征和性质考察。方法以L-苯丙氨酸甲酯盐酸盐为母核,肉豆蔻酰氯、棕榈酰氯、硬脂酰氯为酰化剂,合成一系列脂酰苯丙氨酸凝胶因子,采用IR、1H-NMR、MS等手段对其结构进行表征,并考察其熔点、一级大豆油中的相转变温度和凝胶能力。结果成功合成了C14-L-Phe-OMe、C16-L-Phe-OMe及C18-L-Phe-OMe,并确证了其结构;三种凝胶因子的熔程分别为61.3~63.1、72.1~73.0和62.3~64.1;胶凝能力大小顺序是：C16-L-Phe-OMe〉C18-L-Phe-OMe〉C14-L-Phe-OMe;三种凝胶因子在一级大豆油中的胶凝焓变分别为42.58 k J/mol、22.61 k J/mol和65.01 k J/mol。结论合成的一系列脂酰苯丙氨酸凝胶因子具有较好的胶凝能力,其中C16-L-Phe-OMe的胶凝能力最强,有望作为一种局部给药的长效释药载体。
Objective To synthesize a series of fatty acyl-L-phenylalanine methyl ester gelators including N-myristoyl-L-phenylalanine methyl ester（ C14-L-Phe-OMe）,N-palmityl-L-phenylalanine methyl ester（ C16-L-Phe-OMe）,N-octadecanoyl-L-phenylalanine methyl ester（ C18-L-Phe-OMe）,and to investigate their structural characteristics and property. Methods The gelators including C14-L-Phe-OMe,C16-L-Phe-OMe and C18-L-Phe-OMe were synthesized by reaction of L-phenylalanine methyl ester with chloride including myristoyl chloride,palmityl chloride and octadecanoyl chloride. Their structures were characterized by IR,1H-NMR and MS. The melting points,gelatinizing ability and phase transition temperature in refined soybean oil were investigated. Results The C14-L-Phe-OMe,C16-L-Phe-OMe and C18-L-Phe-OMe were successfully synthesized,moreover,their structures were identified; the melting points of three kinds of gelatins were 61. 3 ~ 63. 1℃,72. 1 ~ 73. 0℃ and 62. 3 ~ 64. 1℃,respectively; the sequence of gelatinizing ability was C16-L-Phe-OMe〉 C18-L-Phe-OMe 〉C14-L-Phe-OMe; the enthalpy（ ΔH） of three kinds of gelators in refined soybean oil was 42. 58 k J / mol,22. 61 k J / mol and 65. 01 k J / mol,respectively. Conclusion The synthesized a series of gelators including C14-L-Phe-OMe,C16-L-Phe-OMe and C18-L-Phe-OMe have better gelatinizing ability in which C16-L-Phe-OMe has the best gelatinizing ability,which is hopeful to be used as a controlled release drug carrier in local medication.
出处
《河北医药》
CAS
2015年第1期24-27,共4页
Hebei Medical Journal
基金
广东省医学科研基金项目(编号:B2014208)
广州市科技计划资助项目(编号:2010Y1-C841)
关键词
超分子有机凝胶
凝胶因子
最低胶凝浓度
supramolecular organogel
gelator
minimal gelling concentration
