title: Protein-mediated dethreading of a biotin-functionalised pseudorotaxane.
abstract: In this article, we describe the synthesis of new biotin-functionalised naphthalene derivatives 3 and 4 and their complexation behaviour with avidin and neutravidin using a range of analytical techniques. We have shown using 2-(4'-hydroxyazobenzene)benzoic acid displacement and ITC experiments, that compounds 3 and 4 have the propensity to form reasonably high-affinity bioconjugates with avidin and neutravidin. We have also demonstrated using (1)H NMR, UV-vis and fluorescence spectroscopy that the naphthalene moiety of 3 and 4 facilitates the formation of pseudorotaxane-like structures with 1 in water. We have then investigated the ability of avidin and neutravidin to modulate the complexation between 1 and 3 or 4. UV-vis and fluorescence spectroscopy has shown that in both cases the addition of the protein disrupts complexation between the naphthalene moieties of 3 and 4 with 1.
authors.affiliation: Glasgow Centre for Physical Organic Chemistry, WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, UK. Graeme.Cooke@glasgow.ac.uk.
authors.forename: Stuart T
authors.initials: ST
authors.lastname: Caldwell
authors.forename: Catherine
authors.initials: C
authors.lastname: Maclean
authors.forename: Mathis
authors.initials: M
authors.lastname: Riehle
authors.forename: Alan
authors.initials: A
authors.lastname: Cooper
authors.forename: Margaret
authors.initials: M
authors.lastname: Nutley
authors.forename: Gouher
authors.initials: G
authors.lastname: Rabani
authors.forename: Brian
authors.initials: B
authors.lastname: Fitzpatrick
authors.forename: Vincent M
authors.initials: VM
authors.lastname: Rotello
authors.forename: Brian O
authors.initials: BO
authors.lastname: Smith
authors.forename: Belal
authors.initials: B
authors.lastname: Khaled
authors.forename: Patrice
authors.initials: P
authors.lastname: Woisel
authors.forename: Graeme
authors.initials: G
authors.lastname: Cooke
mesh_terms: D001360:Avidin / Q000737:chemistry*; D001710:Biotin / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D043862:Rotaxanes / Q000737:chemistry*
chemical_list: D009281:Naphthalenes; D043862:Rotaxanes; D001360:Avidin; D001710:Biotin