槐果碱与水溶性磷酸盐柱[6]芳烃的主客体行为研究

引用本文: 杨云汉, 保秋连, 古捷, 高振杰, 鲁佳佳, 杨举, 杨丽娟. 槐果碱与水溶性磷酸盐柱[6]芳烃的主客体行为研究[J]. 分析化学, 2021, 49(5): 768-778. doi: 10.19756/j.issn.0253-3820.201416 shu

Citation: YANG Yun-Han, BAO Qiu-Lian, GU Jie, GAO Zhen-Jie, LU Jia-Jia, YANG Ju, YANG Li-Juan. Study on Host Guest Behavior of Sophocarpine and Water-soluble Phosphate Salt Pillar[6]arene[J]. Chinese Journal of Analytical Chemistry, 2021, 49(5): 768-778. doi: 10.19756/j.issn.0253-3820.201416 shu

槐果碱与水溶性磷酸盐柱[6]芳烃的主客体行为研究

云南民族大学化学与环境学院云南省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（Nos.21762051，21562048）、云南省高校有机功能分子及材料科技创新团队项目和云南省教育厅科学研究基金项目（Nos.2019Y0193，2020Y0261）资助。

摘要: 采用饱和水溶液法制备了天然药物槐果碱（SOP）和水溶性磷酸盐柱[6]芳烃（PP6A）的包合物（SOP/PP6A）。通过荧光光谱研究了SOP与PP6A的主客体络合性质及化学计量比。采用扫描电子显微镜（SEM）、红外光谱（FT-IR）、X-射线粉末衍射（XRD）和热重（TG）分析对SOP/PP6A包合物进行了表征，采用核磁共振（¹H NMR、2D NMR）、半经验分子轨道法和分子对接推测了SOP/PP6A包合物可能的包合模式。荧光光谱滴定表明，客体分子SOP与主体分子PP6A之间存在着较强的主客体相互作用，采用非线性最小二乘曲线拟合法得到的主客体络合常数为3360 L/mol。等摩尔连续变化法结果表明，主客体化学计量比为1：1；SEM、FT-IR和XRD分析测试结果证明成功制备了包合物；TG分析表明形成包合物后，SOP的热稳定性得到提升；¹H NMR和2D NMR分析结果表明，SOP进入了PP6A的空腔；半经验分子轨道法和分子对接计算表明，PP6A是SOP的良好宿主，主客体空间匹配度高，但主客体间未形成氢键，包合物形成的驱动力主要为疏水作用。本研究为天然药物分子SOP新型药物制剂的研究提供了一种新思路。

关键词:

English

Study on Host Guest Behavior of Sophocarpine and Water-soluble Phosphate Salt Pillar[6]arene

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

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

Received Date: 16 July 2020
Revised Date: 25 March 2021
Fund Project:
Supported by the National Natural Science Foundation of China (Nos. 21562048, 21762051), the Program for Innovative Research Team (in science and technology) in University of Yunnan Province and Yunnan Provincial Department of Education Science Research Fund Project (Nos. 2019Y0193, 2020Y0261).

Abstract: The inclusion compound (SOP/PP6A) of natural medicine sophocarpine (SOP) and water-soluble phosphate salt pillar[6]arene (PP6A) was prepared by saturated aqueous solution method. The host-guest complex properties of SOP and PP6A and their stoichiometric ratio were studied by fluorescence spectroscopy. The SOP/PP6A inclusion complex was characterized by scanning electron microscope (SEM), infrared spectroscopy (FT-IR), X-ray powder diffraction (XRD) and thermos gravimetry (TG), and the nuclear magnetic resonance (¹H NMR, 2D NMR), semi-empirical molecular orbital method and molecular docking speculated the possible inclusion mode of SOP/PP6A inclusion complex. Fluorescence spectroscopy showed that there was a strong host-guest interaction between the guest molecule SOP and the host-guest macrocyclic PP6A. The host-guest complex constant of 3360 L/mol was obtained by the nonlinear least squares curve fitting method. The equimolar continuous change method showed that the host-guest stoichiometric ratio was 1:1. SEM, FT-IR and XRD analysis tests indicated the successful preparation of the inclusion compound. TG analysis showed that the thermal stability of SOP was improved after the formation of the inclusion compound. ¹H NMR and 2D NMR revealed that SOP entered the cavity of PP6A. The semi-empirical molecular orbital method and molecular docking calculations showed that PP6A was a good host for SOP. The host-guest space matching was high, but there was no hydrogen bond formation between the host and guest, and the driving force for the formation of clathrate was mainly hydrophobic. This study provided a selective idea for the research of new drug preparations of natural drug molecule SOP.

Key words:

Sophocarpine
/ Water-soluble phosphate salt pillar[6]arene
/ Inclusion complex
/ Inclusion behavior
/ Theoretical calculation

1. [1]
  LU Y, Xu D, LIU J Y, GU L N. Int. Immunopharmacol., 2019, 70:180-186.
2. [2]
  HE L J, LIU J S, LUO D, ZHENG Y R, ZHANG Y B, WANG G C, LI Y L. Fitoterapia, 2019, 139:104391-104396.
3. [3]
  MA Hu-Qiang, MU Jun, LIU Yang, ZHANG Hong, DING Teng, TIAN Huan, WANG Chun-Liu, LI Ye, LIU Feng. Northwest Pharm. J., 2019, 34(1):84-87. 马虎强, 穆珺, 刘洋, 张红, 丁腾, 田欢, 王春柳, 李晔, 刘峰. 西北药学杂志, 2019, 34(1):84-87.
4. [4]
  ZHANG Ming-Fa, SHEN Ya-Qin. Drug Eval. Res., 2019, 42(3):578-585. 张明发, 沈雅琴. 药物评价研究, 2019, 42(3):578-585.
5. [5]
  LI Min, LIU Xiao-Yun. Northwest Pharma. J., 1996, (5):207-208. 郦敏, 刘晓云. 西北药学杂志, 1996, (5):207-208.
6. [6]
  ZHANG Ai-Hua, ZHANG Yue-Han. Chin. J. Pharm. Anal., 2008, 28(6):964-966. 张爱华, 张悦晗. 药物分析杂志, 2008, 28(6):964-966.
7. [7]
  SUN Peng, YAN Qing-Xiang, DU Tong-Tong, DAI Hang. Asia-Pac. Trad. Med., 2018, 14(11):76-80. 孙朋, 嫣庆祥, 杜同同, 戴航. 亚太传统医药, 2018, 14(11):76-80.
8. [8]
  JIAN Y L, GUO Y Z, ZHAO J C, ZHANG K Z. J. Chromatogr. A, 2007, 1145(1-2):123-127.
9. [9]
  LI Y, WANG G, LIU J, OUYANG L. Eur. J. Med. Chem., 2020, 188:111972-111996.
10. [10]
  WANG R Z, DENG X X, GAO Q X, WU X L, HAN L, GAO X J, ZHAO S Q, CHEN W B, ZHOU R R, LI Z Y, BAI C C. J. Ethnopharmacol., 2020, 248:112172-112193.
11. [11]
  MA T, YAN H, SHI X L, LIU B T, MA Z Q, ZHANG X. Ind. Crops Prod., 2018, 111:149-157.
12. [12]
  WU D Y, ZHU X Y, KANG X D, HUANG H S, YU J L, PAN J, ZHANG X T. Int. Immunopharmacol., 2019, 67:145-151.
13. [13]
  JI Yu-Bin, ZHAO He, WANG Fu-Ling. Chin. Tradit. Herbal Drugs, 2018, 49(20):4945-4948. 季宇彬, 赵贺, 王福玲. 中草药, 2018, 49(20):4945-4948.
14. [14]
  ZHANG P P, WANG P Q, QIAO C P, ZHANG Q, ZHANG J P, CHEN F, ZHANG X, XIE W F, YUAN Z L, LI Z S, CHEN Y X. Cancer Lett., 2016, 376:95-103.
15. [15]
  KRZAK A, BILEWICZ R. Bioelectrochemistry, 2020, 136:107587.
16. [16]
  LI X X, BAI Y X, JI H Y, JIN Z Y. Food Chem., 2020, 321:126750.
17. [17]
  ROY N, BOMZAN P, ROY M N. Chem. Phys. Lett., 2020, 748:137372.
18. [18]
  CHI Shao-Ming, YANG Song-Lin, JIN Wen, YANG Hui-Wen, WANG Yu-Fei, LEI Ze, ZHU Hong-You, ZHAO Yan. Chin. J. Anal. Chem., 2020, 48(2):215-223. 迟绍明, 杨松霖, 晋文, 杨惠文, 王宇飞, 雷泽, 朱洪友, 赵焱. 分析化学, 2020, 48(2):215-223.
19. [19]
  JIN Wen, LI Fei-Yang, HUANG Yu-Rong, YANG Hui-Wen, CHI Shao-Ming, ZHU Hong-You, LEI Ze, ZHAO Yan. Chin. J. Anal. Chem., 2019, 47(8):1235-1242. 晋文, 李飞杨, 黄宇蓉, 杨惠文, 迟绍明, 朱洪友, 雷泽, 赵焱. 分析化学, 2019, 47(8):1235-1242.
20. [20]
  YANG L J, CHANG Q, ZHOU S Y, YANG Y H, XIA F T, CHEN W, Li M Y, YANG X D. Dyes Pigm., 2018, 150:193-201.
21. [21]
  DU Yao, ZHOU Shu-Ya, YANG Yun-Han, YANG Jun-Li, CHEN Wen, YANG Li-Juan. Chin. J. Anal. Chem., 2019, 47(3):371-379. 杜瑶, 周树娅, 杨云汉, 杨俊丽, 陈文, 杨丽娟. 分析化学, 2019, 47(3):371-379.
22. [22]
  ZHAO Fang, ZHAO Xue-Qiu, CHANG Qing, WANG Shu-Hui, DU Yao, YANG Li-Juan. Chin. J. Anal. Chem., 2017, 45(10):1547-1555. 赵芳, 赵雪秋, 常清, 王淑慧, 杜瑶, 杨丽娟. 分析化学, 2017, 45(10):1547-1555.
23. [23]
  YANG L J, WANG S H, ZHOU S Y, ZHAO F, CHANG Q, LI M Y, CHEN W, YANG X D. Mat. Sci. Eng., C, 2017, 76:1136-1145.
24. [24]
  YANG Yun-Han, ZHAO Xue-Qiu, DU Yao, YANG Jun-Li, CHEN Wen, LI Yan-Hua, YANG Li-Juan, CHUAN Yong-Ming. Chin. Tradit. Herbal Drugs, 2019, 50(2):352-362. 杨云汉, 赵雪秋, 杜瑶, 杨俊丽, 陈文, 李燕华, 杨丽娟, 钏永明. 中草药, 2019, 50(2):352-362.
25. [25]
  WHEAT N J, DICKSON K A, KIM R R, NEMATOLLAHI A, MACQUART R B, KAYSER V, YU G C, CHURCH W B, MARSH D J. J. Pharm. Sci., 2016, 105:3615-3625.
26. [26]
  SUN G P, HE Z M, HAO M, XU Z Q, HU X Y, ZHU J J, WANG L Y. Chem. Commun., 2019, 55(73):10892-10895.
27. [27]
  SUN G P, HE Z M, HAO M, ZUO M Z, XU Z Q, HU X Y, ZHU J J, WANG L Y. J. Mater. Chem. B, 2019, 7(25):3944-3949.
28. [28]
  HU X Y, GAO L, MOSEL S, EHLERS M, ZELLERMANN E, JIANG H, KNAUER S K, WANG L Y, SCHMUCK C. Small, 2018, 4(52):1803952.
29. [29]
  ZUO M Z, QIAN W R, XU Z Q, SHAO W, HU X Y, ZHANG D Q, JIANG J L, SUN X Q, WANG L Y. Small, 2018, 14(38):1801942.
30. [30]
  HU X Y, LIU X, ZHANG W Y, QIN S, YAO C H, LI Y, CAO D R, PENG L M, WANG L Y. Chem. Mater., 2016, 28:3778-3790.
31. [31]
  LIU Y, CHEN G S, CHEN Y, LIN J. Biorg. Med. Chem., 2005, 13(12):4037-4042.
32. [32]
  EZÁČ J, HOBZA P. J. Chem. Theory Comput., 2012, 8:141-151.
33. [33]
  MOPAC2016, James J P, Stewart. Stewart Computational Chemistry. Colorado Springs, Co, USA. 2016. HTTP://OpenMOPAC.net.
34. [34]
  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.
35. [35]
  YANG Y H, YANG J L, DU Y, LI C H, WEI K K, LU J J, CHEN W, YANG L J. ACS Omega, 2019, 4(18):17741-17751.
36. [36]
  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, 廖霞俐, 杨波. 分析化学, 2017, 45(5):648-653.

扫一扫看文章

计量

PDF下载量: 17
文章访问数: 1262
HTML全文浏览量: 243

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

槐果碱与水溶性磷酸盐柱[6]芳烃的主客体行为研究

通讯作者: 杨丽娟,E-mail:yangljyang@sina.com

English

Study on Host Guest Behavior of Sophocarpine and 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

槐果碱与水溶性磷酸盐柱[6]芳烃的主客体行为研究

通讯作者: 杨丽娟,E-mail:yangljyang@sina.com

English

Study on Host Guest Behavior of Sophocarpine and 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