Molecular Signal Transduction through Conformational Transmission of a Perhydroanthracene Transducer

Abstract

A biconformational perhydroanthracene 1 was used as a signal transducer. Upon binding of a zinc(II) ion at the bipyridine receptor site, a fluorescence signal is generated at the pyrene effector site.

Trans-2-aminocyclohexanols as pH-triggered molecular switches

“…By affecting these interactions one can control the position of conformational equilibrium of the type 1A 1B, thus controlling the shape and the complexing ability of the macrocycle or podand. These ideas were successfully explored also by Costero et al, [28][29][30][31][32] and were expanded by Koert et al [33][34][35][36][37][38] to cis-decaline and perhydroanthracene derivatives.…”

Biomolecular Materials. Report of the January 13-15, 2002 Workshop

“…Signal amplification (Section 2.1.2) is usually a critical component, as these systems often transduce a change in tens or hundreds of molecules into a physiologically significant response. Many groups have mimicked this stimulus-driven conformational change (Krauss 2000).…”

2,3,6,7-Tetrasubstituted Decalins: Biconformational Transducers for Molecular Signal Transduction

“…This value is comparable with the related binding energy for inducing the triple ring flip in the perhydroanthracene series (∆G ϭ 7.1 kcal mol Ϫ1 ). [4] …”

“…Our goal was to effect a photosignal upon equatorial-to-axial change of the positions 2 and 3. From experience of the perhydroanthracene series, [4] we decided to use pyrene groups [14] at the effector site. The idea behind this was that, in the fluorescence spectrum of the conformer with bis(equatorial) pyrene groups, an excimer signal at 480 nm would primarily be observed, while the decalin conformer with axially linked pyrenes should show a monomer fluorescence at 380 nm as the dominant photosignal.…”

“…[3] Molecular signal transduction by conformational transmission is the product of a conformational change, upon a signal stimulus, at the receptor site. [4] The associated motion is transmitted by the transducer to the effector site, where a second conformational change gives some kind of measurable effect, such as a new signal, a chemical reaction, or a mechanical change. [5] The two-state behavior of biconformational cis-anti-cis-perhydroanthracenes [6] is suited for this purpose.…”