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日用化学工业（中英文）

日用化学工业 ›› 2014, Vol. 44 ›› Issue (9): 494-496.doi: 10.13218/j.cnki.csdc.2014.09.110

• 开发与应用 • 上一篇    下一篇

壬二酸的化学改性及产物抑制酪氨酸酶活性的研究

李杨, 杨子佳, 祝钧, 董银卯   

  1. 北京工商大学 理学院,北京 100048
  • 收稿日期:2014-01-26 发布日期:2019-04-08
  • 通讯作者: 祝 钧,教授,E-mail:zhujun@btbu.edu.cn。
  • 作者简介:李 杨(1988-),女,黑龙江人,硕士研究生,电话:13718907121,E-mail:abcloveliyang@163.com。
  • 基金资助:
    北京市高等学校人才强教计划资助项目(PHR201108094)

Chemical modification of azelaic acid and tyrosinase inhibition activity of the modified product

LI Yang, YANG Zi-jia, ZHU Jun, DONG Yin-mao   

  1. School of Science,Beijing Technology and Business University,Beijing 100048,China
  • Received:2014-01-26 Published:2019-04-08

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摘要： 以壬二酰二氯和氨基酸乙酯盐酸盐为原料,采用改进后的肖顿-鲍曼缩合反应首先合成了壬二酸二丙氨酸乙酯、壬二酸二亮氨酸乙酯和壬二酸二缬氨酸乙酯,然后经过氢氧化钠溶液水解最终得到壬二酰二丙氨酸钠、壬二酰二亮氨酸钠和壬二酰二缬氨酸钠;对两步反应的产物结构采用1HNMR和LC-MS进行表征确认;考察了壬二酸化学改性产物对酪氨酸酶活性的抑制率,并与壬二酰二甘氨酸钾进行了比较。结果表明,通过在壬二酸中引入丙氨酸、亮氨酸和缬氨酸后,其水溶性明显增强,壬二酰二丙氨酸钠、壬二酰二亮氨酸钠和壬二酰二缬氨酸钠对酪氨酸酶活性有明显的抑制作用,随着质量浓度的升高抑制率均随之升高;当4种样品对酪氨酸酶活性的抑制率达到50%时,壬二酰二丙氨酸钠和壬二酰二缬氨酸钠的质量浓度(IC50)约为6.5 g·L-1,阳性对照壬二酰二甘氨酸钾的IC50约为15 g·L-1,与阳性对照壬二酰二甘氨酸钾比较,壬二酰二丙氨酸钠和壬二酰二缬氨酸钠在质量浓度较低时对酪氨酸酶活性发挥更强的抑制效果。

关键词: 壬二酸氨基酸衍生物, 合成, 酪氨酸酶抑制剂

Abstract: Intermediates,ethyl azelaoyl di-alaninate,di-valinatee and di-leucinatee were prepared via the improved Schotten-Bauman condensation with azelaoyl di-chloride and the corresponding amino acid hydrochloride as starting materials.Then the intermediates were hydrolyzed with sodium hydroxide solution and the products sodium salts of corresponding azelaoyl amino acids were obtained.Structures of the products were characterized by 1HNMR and LC-MS.Inhibition ratio of the products on tyrosinase activity was investigated,and compared with that of potassium azelaoyl di-glycine.The results showed that,their water solubility increased significantly and all of the products display strong inhibition effect on the activity of tyrosinase.The inhibition ratio increases as the raise of mass concentration of the products.Comparing with potassium azelaoyl di-glycine,when the inhibition ratio reaches 50%,the mass concentration (IC50) of sodium azelaoyl di-alanine as well as sodium azelaoyl di-valine is 6.5 g·L-1,while that (IC50) of potassium azelaoyl di-glycine is 15 g·L-1.Obviously,at low mass concentrations,inhibiting effect on tyrosinase activity of sodium azelaoyl di-alanine and sodium azelaoyl di-valine is comparatively stronger.

Key words: azelaoyl amino acid derivative, synthesis, tyrosinase inhibitor

中图分类号: 

  • TQ658