A novel organogel of breviscapine via supramolecular self-assembly in DCM

被引:0
作者
Ma, Yan [1 ]
Wang, Jiao [1 ]
Dong, Zhi [1 ]
Yang, Zhizhong [1 ,2 ]
Cao, Tianhai [3 ]
Ma, Yanni [4 ]
Wang, Wenping [1 ,2 ]
机构
[1] Yunnan Univ Chinese Med, Coll Chinese Mat Med, Kunming 650500, Peoples R China
[2] Yunnan Key Lab Southern Med Utilizat, Kunming 650500, Peoples R China
[3] Jida Pharmaceut Co Ltd, Kunming 650500, Peoples R China
[4] Ningxia Med Univ, Gen Hosp, Yinchuan 750004, Peoples R China
基金
中国国家自然科学基金;
关键词
Breviscapine; Organogel; Supramolecular interaction; Self-assembly; Natural product; Low-molecular-weight gelator; DRUG-DELIVERY; GELATORS; GELS; HYDROGEL; DYNAMICS; FEATURES; ACID;
D O I
10.1016/j.molliq.2023.123917
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Supramolecular gels provide great advantages for technological applications. More recently, the natural product gelators (NPGs) has been revealed as an interesting strategy to produce soft materials while combining stimuliresponsiveness and biological activities. However, the discovered NPGs till now was quite rare in spite of the enormous quantity of natural products. Herein, a supramolecular organogel with novel architecture was reported for the first time. Breviscapine (Bre), a natural flavonoid glycoside, was found to be spontaneously forming gels in dichloromethane during the ultrasonication-aided anti-solvent precipitation process. The corresponding xerogel were revealed a spherical network of packed microspheres and maintained a certain crystalline state. Hydrogen bonding and pi-pi stacking were confirmed as the main driving forces for the self-assembly of the organogel by FTIR, NMR and molecular dynamic simulation analysis. Moreover, the obtained Bre organogel showed excellent solvent-retention property and higher skin penetration rate than the pure drug. These would be of great benefit for future discovery of new NPGs and exploration on novel applications of NPG-based gels.
引用
收藏
页数:9
相关论文
共 58 条
  • [1] Personal Perspective on Understanding Low Molecular Weight Gels
    Adams, Dave J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (25) : 11047 - 11053
  • [2] Preparation and Evaluation of Tubular Micelles of Pluronic Lecithin Organogel for Transdermal Delivery of Sumatriptan
    Agrawal, Varsha
    Gupta, Vandana
    Ramteke, Suman
    Trivedi, Piyush
    [J]. AAPS PHARMSCITECH, 2010, 11 (04): : 1718 - 1725
  • [3] Supramolecular Nucleoside-Based Gel: Molecular Dynamics Simulation and Characterization of Its Nanoarchitecture and Self-Assembly Mechanism
    Angelerou, Maria G. F.
    Frederix, Pim W. J. M.
    Wallace, Matthew
    Yang, Bin
    Rodger, Alison
    Adams, Dave J.
    Marlow, Maria
    Zelzer, Mischa
    [J]. LANGMUIR, 2018, 34 (23) : 6912 - 6921
  • [4] Self-assemblyofRenewable Nano-sized Triterpenoids
    Bag, Braja Gopal
    Majumdar, Rakhi
    [J]. CHEMICAL RECORD, 2017, 17 (09) : 841 - 873
  • [5] Self-assembly of a renewable nano-sized triterpenoid 18β-glycyrrhetinic acid
    Bag, Braja Gopal
    Majumdar, Rakhi
    [J]. RSC ADVANCES, 2012, 2 (23): : 8623 - 8626
  • [6] First self-assembly study of betulinic acid, a renewable nano-sized, 6-6-6-6-5 pentacyclic monohydroxy triterpenic acid
    Bag, Braja Gopal
    Dash, Shib Shankar
    [J]. NANOSCALE, 2011, 3 (11) : 4564 - 4566
  • [7] Light-modulation of gel stiffness: a glyconucleoside based bolaamphiphile as a photo-cleavable low molecular weight gelator
    Bansode, Nitin
    Verget, Julien
    Barthelemy, Philippe
    [J]. SOFT MATTER, 2023, 19 (36) : 6867 - 6870
  • [8] Beutler John A, 2009, Curr Protoc Pharmacol, VChapter 9, DOI 10.1002/0471141755.ph0911s46
  • [9] New Application of Proton Nuclear Spin Relaxation Unraveling the Intermolecular Structural Features of Low-Molecular-Weight Organogel Fibers
    Bouguet-Bonnet, Sabine
    Yemloul, Mehdi
    Canet, Daniel
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) : 10621 - 10627
  • [10] B97-3c: A revised low-cost variant of the B97-D density functional method
    Brandenburg, Jan Gerit
    Bannwarth, Christoph
    Hansen, Andreas
    Grimme, Stefan
    [J]. JOURNAL OF CHEMICAL PHYSICS, 2018, 148 (06)