Controlled Molecular Arrangement of Cinnamic Acid in Layered Double Hydroxide through pi-pi Interaction for Controlled Release

被引:0
|
作者
Kim, Taeho [1 ]
Paek, Seung-Min [2 ]
Wang, Kang-Kyun [3 ]
Park, Jin Kuen [4 ]
Salles, Fabrice [5 ]
Oh, Jae-Min [1 ]
机构
[1] Dongguk Univ, Dept Energy & Mat Engn, Seoul 04620, South Korea
[2] Kyungpook Natl Univ, Dept Chem, Daegu 41566, South Korea
[3] BI Biophoton Co Ltd, Gimpo 10090, South Korea
[4] Hankuk Univ Foreign Studies, Dept Chem, Yongin 17035, South Korea
[5] Univ Montpellier, Inst Charles Gerhardt ICGM, ENSCM, CNRS, F-34090 Montpellier, France
关键词
layered double hydroxide; molecular arrangement; phenolic acid; cinnamic acid; pi-pi interaction; release; intermolecular interaction; INTERCALATION; BEHAVIOR; DRUGS;
D O I
10.3390/ijms25084506
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Cinnamic acid (CA) was successfully incorporated into Zn-Al layered double hydroxide (LDH) through coprecipitation. The CA moiety was stabilized in the interlayer space through not only electrostatic interaction but also intermolecular pi-pi interaction. It was noteworthy that the CA arrangement was fairly independent of the charge density of LDH, showing the important role of the layer-CA and CA-CA interactions in molecular stabilization. Computer simulations using the Monte Carlo method as well as analytical approaches including infrared, UV-vis spectroscopy, and differential scanning calorimetry showed the existence of intermolecular interaction. In order to reinforce molecular stabilization, a neutral derivative of CA, cinnamaldehyde (CAD), was additionally incorporated into LDH. It was clearly shown that CAD played a role as a pi-pi interaction mediator to enhance the stabilization of CA. The time-dependent release of CA from LDH was first governed by the layer charge density of LDH; however, the existence of CAD provided additional stabilization to the CA arrangement to slow down the release kinetics.
引用
收藏
页数:15
相关论文
共 50 条
  • [1] Controlled molecular arrangement of easily aggregated deoxycholate with layered double hydroxide
    Lee, Kyounghyoun
    Xie, Jing
    Park, Hyeonjin
    Jung, Hyun
    Oh, Jae-Min
    ROYAL SOCIETY OPEN SCIENCE, 2023, 10 (10):
  • [2] Characterization, physiochemical, controlled release studies of zinc–aluminium layered double hydroxide and zinc layered hydroxide intercalated with salicylic acid
    Nurain Adam
    Sheikh Ahmad Izaddin Sheikh Mohd Ghazali
    Nur Nadia Dzulkifli
    Cik Rohaida Che Hak
    Bulletin of Materials Science, 2021, 44
  • [3] MgAl- Layered Double Hydroxide Nanoparticles for controlled release of Salicylate
    Mondal, Soumini
    Dasgupta, Sudip
    Maji, Kanchan
    MATERIALS SCIENCE & ENGINEERING C-MATERIALS FOR BIOLOGICAL APPLICATIONS, 2016, 68 : 557 - 564
  • [4] Layered double hydroxide/sepiolite hybrid nanoarchitectures for the controlled release of herbicides
    Rebitski, Ediana Paula
    Darder, Margarita
    Aranda, Pilar
    BEILSTEIN JOURNAL OF NANOTECHNOLOGY, 2019, 10 : 1679 - 1690
  • [5] Characterization, physiochemical, controlled release studies of zinc-aluminium layered double hydroxide and zinc layered hydroxide intercalated with salicylic acid
    Adam, Nurain
    Ghazali, Sheikh Ahmad Izaddin Sheikh Mohd
    Dzulkifli, Nur Nadia
    Hak, Cik Rohaida Che
    BULLETIN OF MATERIALS SCIENCE, 2021, 44 (02)
  • [6] Intercalation and controlled release of pharmaceutically active compounds from a layered double hydroxide
    Khan, AI
    Lei, LX
    Norquist, AJ
    O'Hare, D
    CHEMICAL COMMUNICATIONS, 2001, (22) : 2342 - 2343
  • [7] Controlled release of salycilate from the lamella ZnAl layered double hydroxide nanocomposite
    Frunza, M.
    Popa, M. I.
    Hulea, V.
    JOURNAL OF OPTOELECTRONICS AND ADVANCED MATERIALS, 2007, 9 (11): : 3376 - 3378
  • [8] Adsorption of nisin into layered double hydroxide nanohybrids and in-vitro controlled release
    Bouaziz, Zaineb
    Djebbi, Mohamed Amine
    Soussan, Laurence
    Janot, Jean-Marc
    Amara, Abdesslem Ben Haj
    Balme, Sebastien
    MATERIALS SCIENCE AND ENGINEERING C-MATERIALS FOR BIOLOGICAL APPLICATIONS, 2017, 76 : 673 - 683
  • [9] Controlled Release Compound Based on Metanilate-Layered Double Hydroxide Nanohybrid
    Hussein, Mohd Zobir
    Nasir, Norashikin Mat
    Yahaya, Asmah H. J.
    JOURNAL OF NANOSCIENCE AND NANOTECHNOLOGY, 2008, 8 (11) : 5921 - 5928
  • [10] Controlled release of drug from cyclodextrin-intercalated layered double hydroxide
    Nakayama, Hirokazu
    Kuwano, Kouzou
    Tsuhako, Mitsutomo
    JOURNAL OF PHYSICS AND CHEMISTRY OF SOLIDS, 2008, 69 (5-6) : 1552 - 1555