Beilstein J. Org. Chem.2019,15, 2801–2811, doi:10.3762/bjoc.15.273
concentrations potentially allows greater control over certain biological functions. In order to permit remote regulation of Ca2+, a selective BAPTA-type synthetic receptor / host was integrated with a photoswitchable azobenzene motif, which upon photoirradiation would enhance (or diminish) the capacity to bind
μM, respectively). Reversible photoliberation/uptake leading to a variation of free calcium concentration in solution was detected using a fluorescent Ca2+ chemosensor.
Keywords: azobenzene; BAPTA; calcium binding; photorelease; photoswitch; Introduction
In terms of synthetic calcium binding
molecules, since the 1,2-bis(o-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid (BAPTA) scaffold was first described by Tsien, it has been widely used in biological systems and has given rise to a wealth of derivatives [1]. Key to the wide interest in this cation binder are its high specificity for Ca2+ ions
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Graphical Abstract
Figure 1:
Azobenzene-BAPTA 1E and 1Z (a, b, c, d and e denote specific protons), showing idealized Ca2+ uptak...