Encapsulation of cinnamic acid by cucurbit[7]uril for enhancing photoisomerization

Na'il Saleh; Muna S. Bufaroosha; Ziad Moussa; Rukayat Bojesomo; Hebah Al-Amodi; Asia Al-Ahdal

doi:10.3390/molecules25163702

Encapsulation of cinnamic acid by cucurbit[7]uril for enhancing photoisomerization

Na'il Saleh, Muna S. Bufaroosha, Ziad Moussa, Rukayat Bojesomo, Hebah Al-Amodi, Asia Al-Ahdal

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

Cis- or Z-configuration is required for the plant growth-promoting activity of cinnamic acid (CA), whereas the E-form is inactive. Herein, we describe the encapsulation of E-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 that E-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 (α-, β-, and γ-CD). Irradiation of (300 nm) UV light to an aqueous solution of the CB7-bound E isomers induces E to Z photoisomerization and the dissociation of the complex. When the same solution is irradiated by (254 nm) UV light, Z to E conformational changes of the unbound Z isomers are observed and are accompanied by restoring the host-guest complex formation.

Original language	English
Article number	3702
Journal	Molecules
Volume	25
Issue number	16
DOIs	https://doi.org/10.3390/molecules25163702
Publication status	Published - Aug 2020

Keywords

Cis-cinnamic acid
Cucurbituril
Light stimuli
Photoisomerization
Responsiveness

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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10.3390/molecules25163702

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title = "Encapsulation of cinnamic acid by cucurbit[7]uril for enhancing photoisomerization",

abstract = "Cis- or Z-configuration is required for the plant growth-promoting activity of cinnamic acid (CA), whereas the E-form is inactive. Herein, we describe the encapsulation of E-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 that E-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 (α-, β-, and γ-CD). Irradiation of (300 nm) UV light to an aqueous solution of the CB7-bound E isomers induces E to Z photoisomerization and the dissociation of the complex. When the same solution is irradiated by (254 nm) UV light, Z to E conformational changes of the unbound Z isomers are observed and are accompanied by restoring the host-guest complex formation.",

keywords = "Cis-cinnamic acid, Cucurbituril, Light stimuli, Photoisomerization, Responsiveness",

author = "Na'il Saleh and Bufaroosha, {Muna S.} and Ziad Moussa and Rukayat Bojesomo and Hebah Al-Amodi and Asia Al-Ahdal",

note = "Funding Information: Funding: We thank the research program in United Arab Emirates University for financial grant number UPAR (2020) 31S392 and Start-up (2019) 31S401 from the UAE University. Publisher Copyright: {\textcopyright} 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).",

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AU - Bufaroosha, Muna S.

AU - Moussa, Ziad

AU - Bojesomo, Rukayat

AU - Al-Amodi, Hebah

AU - Al-Ahdal, Asia

N1 - Funding Information: Funding: We thank the research program in United Arab Emirates University for financial grant number UPAR (2020) 31S392 and Start-up (2019) 31S401 from the UAE University. Publisher Copyright: © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

PY - 2020/8

Y1 - 2020/8

N2 - Cis- or Z-configuration is required for the plant growth-promoting activity of cinnamic acid (CA), whereas the E-form is inactive. Herein, we describe the encapsulation of E-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 that E-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 (α-, β-, and γ-CD). Irradiation of (300 nm) UV light to an aqueous solution of the CB7-bound E isomers induces E to Z photoisomerization and the dissociation of the complex. When the same solution is irradiated by (254 nm) UV light, Z to E conformational changes of the unbound Z isomers are observed and are accompanied by restoring the host-guest complex formation.

AB - Cis- or Z-configuration is required for the plant growth-promoting activity of cinnamic acid (CA), whereas the E-form is inactive. Herein, we describe the encapsulation of E-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 that E-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 (α-, β-, and γ-CD). Irradiation of (300 nm) UV light to an aqueous solution of the CB7-bound E isomers induces E to Z photoisomerization and the dissociation of the complex. When the same solution is irradiated by (254 nm) UV light, Z to E conformational changes of the unbound Z isomers are observed and are accompanied by restoring the host-guest complex formation.

KW - Cis-cinnamic acid

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KW - Light stimuli

KW - Photoisomerization

KW - Responsiveness

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Encapsulation of cinnamic acid by cucurbit[7]uril for enhancing photoisomerization

Abstract

Keywords

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