TY - JOUR
T1 - Molecular Motors in Aqueous Environment
AU - Lubbe, Anouk S.
AU - Böhmer, Christian
AU - Tosi, Filippo
AU - Szymanski, Wiktor
AU - Feringa, Ben L.
PY - 2018/9/21
Y1 - 2018/9/21
N2 - Molecular motors are Nature's solution for (supra)molecular transport and muscle functioning and are involved in most forms of directional motion at the cellular level. Their synthetic counterparts have also found a myriad of applications, ranging from molecular machines and smart materials to catalysis and anion transport. Although light-driven rotary molecular motors are likely to be suitable for use in an artificial cell, as well as in bionanotechnology, thus far they are not readily applied under physiological conditions. This results mainly from their inherently aromatic core structure, which makes them insoluble in aqueous solution. Here, the study of the dynamic behavior of these motors in biologically relevant media is described. Two molecular motors were equipped with solubilizing substituents and studied in aqueous solutions. Additionally, the behavior of a previously reported molecular motor was studied in micelles, as a model system for the biologically environment. Design principles were established for molecular motors in these media, and insights are given into pH-dependent behavior. The work presented herein may provide a basis for the application of the remarkable properties of molecular motors in more advanced biohybrid systems.
AB - Molecular motors are Nature's solution for (supra)molecular transport and muscle functioning and are involved in most forms of directional motion at the cellular level. Their synthetic counterparts have also found a myriad of applications, ranging from molecular machines and smart materials to catalysis and anion transport. Although light-driven rotary molecular motors are likely to be suitable for use in an artificial cell, as well as in bionanotechnology, thus far they are not readily applied under physiological conditions. This results mainly from their inherently aromatic core structure, which makes them insoluble in aqueous solution. Here, the study of the dynamic behavior of these motors in biologically relevant media is described. Two molecular motors were equipped with solubilizing substituents and studied in aqueous solutions. Additionally, the behavior of a previously reported molecular motor was studied in micelles, as a model system for the biologically environment. Design principles were established for molecular motors in these media, and insights are given into pH-dependent behavior. The work presented herein may provide a basis for the application of the remarkable properties of molecular motors in more advanced biohybrid systems.
KW - UNIDIRECTIONAL ROTARY MOTION
KW - SINGLE STEREOGENIC CENTER
KW - THERMAL HELIX INVERSION
KW - STRUCTURAL MODIFICATION
KW - PHOTOSWITCHABLE INHIBITORS
KW - REVERSIBLE PHOTOREGULATION
KW - AZOBENZENE PHOTOSWITCHES
KW - ANTIBACTERIAL ACTIVITY
KW - PROTEASOME INHIBITORS
KW - SECONDARY STRUCTURE
U2 - 10.1021/acs.joc.8b01627
DO - 10.1021/acs.joc.8b01627
M3 - Article
SN - 0022-3263
VL - 83
SP - 11008
EP - 11018
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 18
ER -