高丽槐素与水溶性磷酸盐柱[6]芳烃包合物的制备、表征及分子模拟研究

引用本文: 陶欣, 张郡童, 杨云汉, 杨举, 苏丽娇, 陈艳, 杨明坤, 杨丽娟. 高丽槐素与水溶性磷酸盐柱[6]芳烃包合物的制备、表征及分子模拟研究[J]. 分析化学, 2023, 51(2): 219-228. doi: 10.19756/j.issn.0253-3820.221469 shu

Citation: TAO Xin, ZHANG Jun-Tong, YANG Yun-Han, YANG Ju, SU Li-Jiao, CHEN Yan, YANG Ming-Kun, YANG Li-Juan. Preparation, Characterization and Molecular Modeling Studies of Inclusion Complex of Vincamine With Water-Soluble Phosphate Salt Pillar[6]Arene[J]. Chinese Journal of Analytical Chemistry, 2023, 51(2): 219-228. doi: 10.19756/j.issn.0253-3820.221469 shu

高丽槐素与水溶性磷酸盐柱[6]芳烃包合物的制备、表征及分子模拟研究

云南民族大学化学与环境学院, 云南省高校智能超分子化学重点实验室,生物基材料绿色制备技术国家地方联合工程中心, 昆明 650500

通讯作者: 杨丽娟,E-mail:yangljyang@sina.com

基金项目:
国家自然科学基金项目(No.21762051)、云南省兴滇人才支持计划项目、云南省高校有机功能分子及材料科技创新团队项目和研究生基金项目(No.2022SKY031)资助。

摘要: 以水溶性磷酸盐柱[6]芳烃（PP6A）为主体，天然药物高丽槐素（MAA）为客体，采用饱和溶液法构建了一种新型的主客体包合物MAA/PP6A。以包合物的载药量为指标，通过正交试验优化MAA/PP6A包合物的制备工艺；采用荧光光谱法、扫描电子显微镜（SEM）、X-射线粉末衍射（XRD）和傅里叶红外光谱（FT-IR）对MAA/PP6A包合物进行表征；运用核磁共振、分子模拟对接、半经验分子轨道法研究了MAA与PP6A包合物的包合模式。正交实验结果表明，包合物的最优制备条件为： PP6A与MAA物质的量之比为2∶1，温度为50℃，制备时间为8 h，乙醇与水的体积比为1∶1。荧光光谱滴定结果表明，MAA与PP6A之间的包合比为1∶1，并且主客体之间有较强的相互作用；采用非线性最小二乘曲线拟合法计算得到主客体络合常数为2.458×10⁴ L/mol；分析测试结果表明，MAA/PP6A包合物已制备成功；MAA与PP6A形成包合物后，其水溶性从0.3463 mg/mL提高至6.123 mg/mL，有效改善了MAA的水溶性。半经验分子轨道法和分子对接计算结果表明，主客体之间存在弱相互作用，MAA进入PP6A的空腔中形成构象稳定的包合物，PP6A是MAA的良好宿主，最优包合模式与核磁共振研究结果一致。

关键词:

English

Preparation, Characterization and Molecular Modeling Studies of Inclusion Complex of Vincamine With Water-Soluble Phosphate Salt Pillar[6]Arene

National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, Key Laboratory of Intelligent Supramolecular Chemistry at the University of Yunnan Province, School of Chemistry & Environment, Yunnan Minzu University, Kunming 650500, China

Corresponding author: YANG Li-Juan, yangljyang@sina.com

Received Date: 22 September 2022
Revised Date: 08 December 2022
Fund Project:
Supported by the National Natural Science Foundation of China (No. 21762051), the Program for Xingdian Talents (Jiaoxue Mingshi), the Program for Innovative Research Team (in science and technology) in University of Yunnan Province and the Postgraduate Fund (No. 2022SKY031).

Abstract: A novel host-guest inclusion complex MAA/PP6A was constructed by the saturated solution method with water-soluble phosphate salt pillar[6]arene (PP6A) as the host and the natural medicine maackiain (MAA) as the guest. The preparation process of MAA/PP6A clathrate was screened by orthogonal test with the drug loading of clathrate as an index. The inclusion complex MAA/PP6A was characterized by fluorescence spectroscopy, scanning electron microscope (SEM), X-ray powder diffraction (XRD), and infrared spectroscopy (FT-IR). The inclusion mode of MAA and PP6A inclusion complex was studied by nuclear magnetic resonance spectroscopy (NMR), molecular simulation docking and semi-empirical molecular orbital methods. The results of orthogonal experiments showed that the optimal conditions for the preparation of the inclusion complex were as follows: the mass ratio of PP6A to MAA was 2:1, the volume ratio of ethanol to water was 1:1, and reaction at 50 ℃ for 8 h. Fluorescence spectroscopic titration experiment showed that the inclusion ratio between MAA and PP6A was 1:1 and there was a strong interaction between the host and the guest. The host-guest complex constant was calculated to be 2.458×10⁴ L/mol by the non-linear least squares curve fitting method. Analytical test results showed that the inclusion complex was successfully prepared. The water solubility of MAA increased from 0.3463 to 6.123 mg/mL after the formation of the inclusion complex between MAA and PP6A, which effectively improved the water solubility of MAA. Semi-empirical molecular orbital method and molecular docking calculations indicated that there was no hydrogen bond formed between the host and the guest. MAA could enter the cavity of PP6A and formed a conformationally stable inclusion complex. PP6A was a good host for MAA, and the optimal mode was consistent with the NMR results.

Key words:

Maackiain
/ Water-soluble phosphate salt pillar[6]arene
/ Inclusion behavior
/ Molecule docking
/ Molecule dynamics

1. [1]
  CHEN Lu, ZHAO Jing, LIANG Li-Wei, GAO Xiao-Li. Northwest Pharm. J., 2018, 33(3):364-368. 陈露, 赵静, 梁丽薇, 高晓黎. 西北药学杂志, 2018, 33(3):364-368.
2. [2]
  WANG Xiao-Lin, ZHENG Xiao-Xiao, HUANG Feng, TANG Guo-Lin, WANG Wen, JIANG Gui-Hua, LI Pei, ZHAO Yan. West China J. Pharm. Sci., 2018, 33(3):245-250. 王潇霖, 郑潇潇, 黄凤, 唐国琳, 王雯, 蒋桂华, 李培, 赵燕. 华西药学杂志, 2018, 33(3):245-250.
3. [3]
  DU Shun-Xia, MENG Xue-Fang, WANG Liu-Ping, LIANG Qiu-Yun, XIE Chan, HUANG Ben-Yang. J. Guangxi Med. Univ., 2017, 34(8):1237-1240. 杜顺霞, 蒙雪芳, 王柳萍, 梁秋云, 谢婵, 黄本杨. 广西医科大学学报, 2017, 34(8):1237-1240.
4. [4]
  LEE H W, RYU H W, KANG M G, PARK D, OH S R, KIM H. Bioorg. Med. Chem. Lett., 2016, 26(19):4714-4719.LEE H W, RYU H W, KANG M G, PARK D, OH S R, KIM H. Bioorg. Med. Chem. Lett., 2016, 26(19):4714-4719.
5. [5]
  LIU Y H, ZENG W Z, MA C, WANG Z Y, WANG C, LI S B, HE W, ZHANG Q, XU J K, ZHOU C. J. Cell. Mol. Med., 2020, 24(21):12308-12317.LIU Y H, ZENG W Z, MA C, WANG Z Y, WANG C, LI S B, HE W, ZHANG Q, XU J K, ZHOU C. J. Cell. Mol. Med., 2020, 24(21):12308-12317.
6. [6]
  YANG Xin-Zhou, LV Jing-Nan, XU Chan, LIN Qin-Xiong, YANG Jing, WANG Chao, SONG Ping. J. Yunnan Univ., Nat. Sci. Ed., 2015, 37(1):134-139. 杨新洲, 吕静南, 徐婵, 林亲雄, 杨静, 汪超, 宋萍. 云南大学学报:自然科学版, 2015, 37(1):134-139.
7. [7]
  ARATANECHEMUGE Y, HIBASAMI H, KATSUZAKI H, IMAI K, KOMIYA T. Oncol Rep., 2004, 12(6):1183.ARATANECHEMUGE Y, HIBASAMI H, KATSUZAKI H, IMAI K, KOMIYA T. Oncol Rep., 2004, 12(6):1183.
8. [8]
  ZENG Y T, JIANG J M, LAO H Y, GUO J W, LUN Y N, YANG M. Mol. Med. Rep., 2015, 11(3):2234-2240.ZENG Y T, JIANG J M, LAO H Y, GUO J W, LUN Y N, YANG M. Mol. Med. Rep., 2015, 11(3):2234-2240.
9. [9]
  LAN Jun-Jie, ZHANG Hua, LOU Hua-Yong, WU Hong-Guo, PAN Wei-Dong. J. Trop. Subtrop. Bot., 2016, 24(4):471-476. 蓝俊杰, 张华, 娄华勇, 吴红果, 潘卫东. 热带亚热带植物学报, 2016, 24(4):471-476.
10. [10]
  MIZUGUCHI H, NARIAI Y, KATO S, NAKANO T, KANAYAMA T, KASHIWADA Y, NEMOTO H, KAWAZOE K, TAKAISHI Y, KITAMURA Y, TAKEDA N, FUKUI H. Pharmacol. Res. Perspect., 2015, 3(5):e00166.MIZUGUCHI H, NARIAI Y, KATO S, NAKANO T, KANAYAMA T, KASHIWADA Y, NEMOTO H, KAWAZOE K, TAKAISHI Y, KITAMURA Y, TAKEDA N, FUKUI H. Pharmacol. Res. Perspect., 2015, 3(5):e00166.
11. [11]
  PENG T, ZHAO F, CHEN X, JIANG G, WANG S. Biomed. Rep., 2016, 4(2):219-222.PENG T, ZHAO F, CHEN X, JIANG G, WANG S. Biomed. Rep., 2016, 4(2):219-222.
12. [12]
  Editorial Board of Chinese Materia Medica, State Administration of Traditional Chinese Medicine, Shanghai:Shanghai Science and Technology Press, 1999:571-572. 国家中医药管理局《中华本草》编委会. 上海:上海科学技术出版社, 1999:571-572.
13. [13]
  WANG Xiao-Lin, HUANG Feng, ZHENG Xiao-Xiao, TANG Guo-Lin, WANG Wen, JIANG Gui-Hua. Pharm. Clin. Chin. Mater. Med., 2017, 8(6):46-49, 53. 王潇霖, 黄凤, 郑潇潇, 唐国林, 王雯, 蒋桂华. 中药与临床, 2017, 8(6):46-49, 53.
14. [14]
  LUO T, HUANG J, LIU J. Chem. Res. Chin. Univ., 2020, 36(6):1091-1096.LUO T, HUANG J, LIU J. Chem. Res. Chin. Univ., 2020, 36(6):1091-1096.
15. [15]
  XIE J, ZENG Z, TAO Z, ZHANG Q. Chem. Res. Chin. Univ., 2020, 36(5):804-809.XIE J, ZENG Z, TAO Z, ZHANG Q. Chem. Res. Chin. Univ., 2020, 36(5):804-809.
16. [16]
  JI X, LI Y, WANG H, ZHAO R, TANG G, HUANG F. Polym. Chem., 2015, 6(28):5021-5025.JI X, LI Y, WANG H, ZHAO R, TANG G, HUANG F. Polym. Chem., 2015, 6(28):5021-5025.
17. [17]
  OGOSHI T, KANAI S, FUJINAMI S, YAMAGISHI T, NAKAMOTO Y. J. Am. Chem. Soc., 2008, 130(15):5022-5023.OGOSHI T, KANAI S, FUJINAMI S, YAMAGISHI T, NAKAMOTO Y. J. Am. Chem. Soc., 2008, 130(15):5022-5023.
18. [18]
  XUE M, YANG Y, CHI X, ZHANG Z, HUANG F. Acc. Chem. Res., 2012, 45(8):1294-1308.XUE M, YANG Y, CHI X, ZHANG Z, HUANG F. Acc. Chem. Res., 2012, 45(8):1294-1308.
19. [19]
  DUAN Q, CAO Y, LI Y, HU X, XIAO T, LIN C, PAN Y, WANG L. J. Am. Chem. Soc., 2013, 135(28):10542-10549.DUAN Q, CAO Y, LI Y, HU X, XIAO T, LIN C, PAN Y, WANG L. J. Am. Chem. Soc., 2013, 135(28):10542-10549.
20. [20]
  PAN S, NI M, MU B, LI Q, HU X Y, LIN C, CHEN D, WANG L. Adv. Funct. Mater., 2015, 25(23):3571-3580.PAN S, NI M, MU B, LI Q, HU X Y, LIN C, CHEN D, WANG L. Adv. Funct. Mater., 2015, 25(23):3571-3580.
21. [21]
  HU X Y, LIU X, ZHANG W, QIN S, YAO C, LI Y, CAO D, PENG L, WANG L. Chem. Mater., 2016, 28(11):3778-3788.HU X Y, LIU X, ZHANG W, QIN S, YAO C, LI Y, CAO D, PENG L, WANG L. Chem. Mater., 2016, 28(11):3778-3788.
22. [22]
  SUN Tao, WANG Yi-Bo. Chem. J. Chin. Univ., 2020, 41(9):2046-2053. 孙涛, 王一波. 高等学校化学学报, 2020, 41(9):2046-2053.
23. [23]
  ZHANG Lai-Xin, MA Lin. Contemp. Chem. Ind., 2015, 44(4):723-725. 张来新, 马琳. 当代化工, 2015, 44(4):723-725.
24. [24]
  WHEATE N J, DICKSON K A, KIM R R, NEMATOLLAHI A, MACQUART R B, KAYSER V, YU G, CHURCH W B, MARSH D J. J. Pharm. Sci., 2016, 105(12):3615-3625.WHEATE N J, DICKSON K A, KIM R R, NEMATOLLAHI A, MACQUART R B, KAYSER V, YU G, CHURCH W B, MARSH D J. J. Pharm. Sci., 2016, 105(12):3615-3625.
25. [25]
  ZHOU J Y, XU H, TONG Z Z, YANG Y H, JIANG G H. Mater. Sci. Eng., 2018, 89:237-244.ZHOU J Y, XU H, TONG Z Z, YANG Y H, JIANG G H. Mater. Sci. Eng., 2018, 89:237-244.
26. [26]
  LIU Y, CHEN G S, CHEN Y, LIN J. Bioorg. Med. Chem., 2005, 13(12):4037-4042.LIU Y, CHEN G S, CHEN Y, LIN J. Bioorg. Med. Chem., 2005, 13(12):4037-4042.
27. [27]
  ŘEZÁČ J, HOBZA P. J. Chem. Theor. Comput., 2012, 8(1):141-151.ŘEZÁČ J, HOBZA P. J. Chem. Theor. Comput., 2012, 8(1):141-151.
28. [28]
  MOPAC2016, JAMES J P, Stewart. Stewart Computation Chemistry. Colorado Springs, Co, USA. 2016. HTTP//OpenMOPAC.net.MOPAC2016, JAMES J P, Stewart. Stewart Computation Chemistry. Colorado Springs, Co, USA. 2016. HTTP//OpenMOPAC.net.
29. [29]
  MORRIS G M, HUEY R, LINDSTROM W, SANNER M F, BELEW R K, GOODSELL D S, OLSON A J. J. Comput. Chem., 2009, 30(16):2785-2791.MORRIS G M, HUEY R, LINDSTROM W, SANNER M F, BELEW R K, GOODSELL D S, OLSON A J. J. Comput. Chem., 2009, 30(16):2785-2791.
30. [30]
  REN Ke, ZAHNG Zhi-Rong, JU Jing-Hong, LIU Yang, GONG Tao. Chin. Tradit. Herb. Drugs, 2008, 39(4):518-521. 任科, 张志荣, 鞠静红, 刘阳, 龚涛. 中草药, 2008, 39(4):518-521.
31. [31]
  YANG B, LIN J, CHEN Y, LIU Y. Bioorg. Med. Chem., 2009, 17(17):6311-6317.YANG B, LIN J, CHEN Y, LIU Y. Bioorg. Med. Chem., 2009, 17(17):6311-6317.
32. [32]
  YANG Yun-Han, BAO Qiu-Lian, GU Jie, GAO Zhen-Jie, LU Jia-Jia, YANG Ju, YANG Li-Juan. Chin. J. Anal. Chem., 2021, 49(5):768-778. 杨云汉, 保秋连, 古捷, 高振杰, 鲁佳佳, 杨举, 杨丽娟. 分析化学, 2021, 49(5):768-778.
33. [33]
  ROY N, BOMZAN P, NATH ROY M. Chem. Phys. Lett., 2020, 748:137372.ROY N, BOMZAN P, NATH ROY M. Chem. Phys. Lett., 2020, 748:137372.
34. [34]
  DENG Ying-Hui, SU Li-Na, PANG Yan-Hua, GUO Ya-Fei, WANG Fen, LIAO Xia-Li, YANG Bo. Chin. J. Anal. Chem., 2017, 45(5):648-653. 邓颖慧, 苏丽娜, 庞艳华, 郭亚飞, 王芬, 廖霞丽, 杨波. 分析化学, 2017, 45(5):648-653
35. [35]
  KŘÍŽ K, ŘEZÁČ J. J. Chem. Inf. Model., 2020, 60(3):1453-1460.KŘÍŽ K, ŘEZÁČ J. J. Chem. Inf. Model., 2020, 60(3):1453-1460.
36. [36]
  MONTASSIER P, DUCHÊNE D, POELMAN M C. Int. J. Pharm., 1997, 153(2):199-209.MONTASSIER P, DUCHÊNE D, POELMAN M C. Int. J. Pharm., 1997, 153(2):199-209.

扫一扫看文章

计量

PDF下载量: 8
文章访问数: 760
HTML全文浏览量: 93

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

高丽槐素与水溶性磷酸盐柱[6]芳烃包合物的制备、表征及分子模拟研究

通讯作者: 杨丽娟,E-mail:yangljyang@sina.com

English

Preparation, Characterization and Molecular Modeling Studies of Inclusion Complex of Vincamine With Water-Soluble Phosphate Salt Pillar[6]Arene

Corresponding author: YANG Li-Juan, yangljyang@sina.com

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

高丽槐素与水溶性磷酸盐柱[6]芳烃包合物的制备、表征及分子模拟研究

通讯作者: 杨丽娟,E-mail:yangljyang@sina.com

English

Preparation, Characterization and Molecular Modeling Studies of Inclusion Complex of Vincamine With Water-Soluble Phosphate Salt Pillar[6]Arene

Corresponding author: YANG Li-Juan, yangljyang@sina.com

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs