Encapsulation of Cinnamic Acid by Cucurbit[7]uril for Enhancing Photoisomerization

被引：5

作者：

Saleh, Na'il ^{[1
]}

Bufaroosha, Muna S. ^{[1
]}

Moussa, Ziad ^{[1
]}

Bojesomo, Rukayat ^{[1
]}

Al-Amodi, Hebah ^{[1
]}

Al-Ahdal, Asia ^{[1
]}

机构：

[1] United Arab Emirates Univ, Coll Sci, Dept Chem, POB 15551, Al Ain, U Arab Emirates

来源：

MOLECULES | 2020年 / 25卷 / 16期

关键词：

cis-cinnamic acid; cucurbituril; photoisomerization; responsiveness; light stimuli; BETA-CYCLODEXTRIN; CRYSTAL-STRUCTURE; PHOTODIMERIZATION; CATALYSIS; EMISSION;

D O I：

10.3390/molecules25163702

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：

Cis- orZ-configuration is required for the plant growth-promoting activity of cinnamic acid (CA), whereas theE-form is inactive. Herein, we describe the encapsulation ofE-CA by cucurbit[7]uril (CB7) and show that photoisomerization reactions can be more efficiently controlled in aqueous solutions by utilizing this supramolecular approach. Measurements of UV-visible absorption and proton NMR spectra at different pH values confirm thatE-CA and its methyl ester, methyl-E-cinnamate (MC), form stronger 1:1 host-guest complexes with CB7 compared to cucurbit[8]uril (CB8) or three cyclodextrins (alpha-, beta-, and gamma-CD). Irradiation of (300 nm) UV light to an aqueous solution of the CB7-boundEisomers inducesEtoZphotoisomerization and the dissociation of the complex. When the same solution is irradiated by (254 nm) UV light,ZtoEconformational changes of the unboundZisomers are observed and are accompanied by restoring the host-guest complex formation.

引用

页数：11

共 50 条

[21] Encapsulation of cisplatin by cucurbit[7]uril decreases the neurotoxic and cardiotoxic side effects of cisplatin
Oun, Rabbab
Plumb, Jane
Rowan, Edward
Wheate, Nial
TOXICOLOGY LETTERS, 2013, 221 : S92 - S92
[22] Supramolecular Encapsulation of Vitamin B6 by Macrocyclic Nanocontainer Cucurbit[7]uril
Li, Wanying
Li, Shengke
Wyman, Ian W.
Macartney, Donal H.
Zhang, Qingwen
Zheng, Ying
Wang, Ruibing
JOURNAL OF NANOMATERIALS, 2015, 2015
[23] Inclusion complexation of diquat and paraquat by the hosts cucurbit[7]uril and cucurbit[8]uril
Ling, Yonghua
Mague, Joel T.
Kaifer, Angel E.
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (28) : 7908 - 7914
[24] Toxicity of cucurbit[7]uril and cucurbit[8]uril: an exploratory in vitro and in vivo study
Uzunova, Vanya D.
Cullinane, Carleen
Brix, Klaudia
Nau, Werner M.
Day, Anthony I.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (09) : 2037 - 2042
[25] Inclusion of methylviologen in cucurbit[7]uril
Kim, HJ
Jeon, WS
Ko, YH
Kim, K
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (08) : 5007 - 5011
[26] Synthesis and Electronic Properties of 1,2-Hemisquarimines and Their Encapsulation in a Cucurbit[7] uril Host
De Filippo, Christian C.
Tang, Hao
Ravotto, Luca
Bergamini, Giacomo
Salice, Patrizio
Mba, Miriam
Ceroni, Paola
Galoppini, Elena
Maggini, Michele
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (21) : 6412 - 6420
[27] Supramolecular Encapsulation and Bioactivity Modulation of a Halonium Ion by Cucurbit[n]uril (n=7, 8)
Yin, Hang
Huang, Qiaoxian
Zhao, Wenwen
Bardelang, David
Siri, Didier
Chen, Xiuping
Lee, Simon M. Y.
Wang, Ruibing
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (08): : 4882 - 4887
[28] Supramolecular Control of Reactivity toward Hydrolysis of 7-Diethylaminocoumarin Schiff Bases by Cucurbit[7]uril Encapsulation
Alcazar, Jackson J.
Geue, Niklas
Valladares, Veronica
Canete, Alvaro
Perez, Edwin G.
Garcia-Rio, Luis
Santos, Jose G.
Aliaga, Margarita E.
ACS OMEGA, 2021, 6 (15): : 10333 - 10342
[29] Trifluoromethanesulfonate Anion-linked Supramolecular Frameworks of Cucurbit[5]uril and Cucurbit[7]uril
Zhang, Jie
Ren, Huifang
Liu, Li
CHEMISTRY LETTERS, 2010, 39 (09) : 1016 - 1017
[30] Binding modes of cucurbit[6]uril and cucurbit[7]uril with a tetracationic bis(viologen) guest
Yuan, Lina
Wang, Ruibing
Macartney, Donal H.
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (12): : 4539 - 4542

← 1 2 3 4 5 →