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 journalArticleAcademicpeer-review

16 Citations (Scopus)
81 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 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.

Original languageEnglish
Pages (from-to)813-817
Number of pages5
JournalChemistry: a European journal
Volume24
Issue number4
DOIs
Publication statusPublished - 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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