Photo-responsive Bioactive Surfaces Based on Cucurbit[8]uril-Mediated Host-Guest Interactions of Arylazopyrazoles

Maike Wiemann; Rebecca Niebuhr; Alberto  Juan; Emanuela Cavatorta; Bart Jan Ravoo; Pascal Jonkheijm

doi:10.1002/chem.201705426

Photo-responsive Bioactive Surfaces Based on Cucurbit[8]uril-Mediated Host-Guest Interactions of Arylazopyrazoles

Maike Wiemann, Rebecca Niebuhr, Alberto Juan, Emanuela Cavatorta, Bart Jan Ravoo^* (Corresponding Author), Pascal Jonkheijm (Corresponding Author)

^*Corresponding author for this work

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

19 Citations (Scopus)

126 Downloads (Pure)

Abstract

A photoswitchable arylazopyrazole (AAP) derivative binds with cucurbit[8]uril (CB[8]) and methylviologen (MV²⁺) to form a 1:1:1 heteroternary host-guest complex with a binding constant of K_a=2×10³m^-1. The excellent photoswitching properties of AAP are preserved in the inclusion complex. Irradiation with light of a wavelength of 365 and 520nm leads to quantitative E- to Z- isomerization and vice versa, respectively. Formation of the Z-isomer leads to dissociation of the complex as evidenced using ¹HNMR spectroscopy. AAP derivatives are then used to immobilize bioactive molecules and photorelease them on demand. When Arg-Gly-Asp-AAP (AAP-RGD) peptides are attached to surface bound CB[8]/MV²⁺ complexes, cells adhere and can be released upon irradiation. The heteroternary host-guest system offers highly reversible binding properties due to efficient photoswitching and these properties are attractive for designing smart surfaces.

Original language	English
Pages (from-to)	813-817
Number of pages	5
Journal	Chemistry : a European journal
Volume	24
Issue number	4
DOIs	https://doi.org/10.1002/chem.201705426
Publication status	Published - 19 Jan 2018

Keywords

UT-Hybrid-D
Cucurbit[8]uril
Host-guest systems
Photo-responsive
Stimuli-responsive
Arylazopyrazoles
host–guest systems
photo-responsive
arylazopyrazoles
cucurbit[8]uril
stimuli-responsive

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Wiemann2018photo-responsiveFinal published version, 969 KBLicence: CC BY-NC-ND

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title = "Photo-responsive Bioactive Surfaces Based on Cucurbit[8]uril-Mediated Host-Guest Interactions of Arylazopyrazoles",

abstract = "A photoswitchable arylazopyrazole (AAP) derivative binds with cucurbit[8]uril (CB[8]) and methylviologen (MV2+) to form a 1:1:1 heteroternary host-guest complex with a binding constant of Ka=2×103m-1. The excellent photoswitching properties of AAP are preserved in the inclusion complex. Irradiation with light of a wavelength of 365 and 520nm leads to quantitative E- to Z- isomerization and vice versa, respectively. Formation of the Z-isomer leads to dissociation of the complex as evidenced using 1HNMR spectroscopy. AAP derivatives are then used to immobilize bioactive molecules and photorelease them on demand. When Arg-Gly-Asp-AAP (AAP-RGD) peptides are attached to surface bound CB[8]/MV2+ complexes, cells adhere and can be released upon irradiation. The heteroternary host-guest system offers highly reversible binding properties due to efficient photoswitching and these properties are attractive for designing smart surfaces.",

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author = "Maike Wiemann and Rebecca Niebuhr and Alberto Juan and Emanuela Cavatorta and Ravoo, {Bart Jan} and Pascal Jonkheijm",

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AU - Juan, Alberto

AU - Cavatorta, Emanuela

AU - Ravoo, Bart Jan

AU - Jonkheijm, Pascal

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AB - A photoswitchable arylazopyrazole (AAP) derivative binds with cucurbit[8]uril (CB[8]) and methylviologen (MV2+) to form a 1:1:1 heteroternary host-guest complex with a binding constant of Ka=2×103m-1. The excellent photoswitching properties of AAP are preserved in the inclusion complex. Irradiation with light of a wavelength of 365 and 520nm leads to quantitative E- to Z- isomerization and vice versa, respectively. Formation of the Z-isomer leads to dissociation of the complex as evidenced using 1HNMR spectroscopy. AAP derivatives are then used to immobilize bioactive molecules and photorelease them on demand. When Arg-Gly-Asp-AAP (AAP-RGD) peptides are attached to surface bound CB[8]/MV2+ complexes, cells adhere and can be released upon irradiation. The heteroternary host-guest system offers highly reversible binding properties due to efficient photoswitching and these properties are attractive for designing smart surfaces.

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Photo-responsive Bioactive Surfaces Based on Cucurbit[8]uril-Mediated Host-Guest Interactions of Arylazopyrazoles

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