Dataset Information

Synthesis and testing of the first azobenzene mannobioside as photoswitchable ligand for the bacterial lectin FimH.

ABSTRACT: In order to allow spatial and temporal control of carbohydrate-specific bacterial adhesion, it has become our goal to synthesise azobenzene mannosides as photoswitchable inhibitors of type 1 fimbriae-mediated adhesion of E. coli. An azobenzene mannobioside 2 was prepared and its photochromic properties were investigated. The E?Z isomerisation was found to be highly effective, yielding a long-lived (Z)-isomer. Both isomers, E and Z, show excellent water solubility and were tested as inhibitors of mannoside-specific bacterial adhesion in solution. Their inhibitory potency was found to be equal and almost two orders of magnitude higher than that of the standard inhibitor methyl mannoside. These findings could be rationalised on the basis of computer-aided docking studies. The properties of the new azobenzene mannobioside have qualified this glycoside to be eventually employed on solid support, in order to fabricate photoswitchable adhesive surfaces.

SUBMITTER: Chandrasekaran V

PROVIDER: S-EPMC3566865 | biostudies-literature | 2013

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Synthesis and testing of the first azobenzene mannobioside as photoswitchable ligand for the bacterial lectin FimH.

Chandrasekaran Vijayanand V Kolbe Katharina K Beiroth Femke F Lindhorst Thisbe K TK

Beilstein journal of organic chemistry 20130201

In order to allow spatial and temporal control of carbohydrate-specific bacterial adhesion, it has become our goal to synthesise azobenzene mannosides as photoswitchable inhibitors of type 1 fimbriae-mediated adhesion of E. coli. An azobenzene mannobioside 2 was prepared and its photochromic properties were investigated. The E→Z isomerisation was found to be highly effective, yielding a long-lived (Z)-isomer. Both isomers, E and Z, show excellent water solubility and were tested as inhibitors of ...[more]

PMID: 23399876

Similar Datasets

Project description:In the vast majority of studies on semiconductor particles ligands or capping agents are used that bind to the surface of the particles covering them with an electrically insulating shell. Since the transport of charge carriers and/or energy across interfaces is desirable for a variety of applications, the use of ?-conjugated ligands becomes increasingly interesting. Among them are compounds that react to external stimuli. Molecular switches in particular are fascinating because the properties of the interfaces can be potentially adjusted as required. However, there is debate about how the properties of such special ligands are influenced by the presence of a semiconductor and vice versa. Here ammonium-modified azobenzene compounds were selected as prototypes for molecular switches and organic-inorganic hybrid perovskites as semiconductor materials. The class of ammonium-lead-halide phases as prototypes is peculiar because, in addition to the surface functionalization of 3D crystals, organic compounds can actually be incorporated into the crystal as 2D phases. Thus, for example, layered Ruddlesden-Popper phases are obtained. We present photoswitchable azobenzene ligands with different head-group lengths for the synthesis of 2D and 3D hybrid perovskite phases. The energy transfer mechanisms are influenced by the length of the molecular spacer moiety, which determines the distance between the ? system and the semiconductor surfaces. We find huge differences in the photoswitching behaviour between the free, surface-coordinated and integrated ligands between the perovskite layers. Photoswitching of azobenzene ligands incorporated in 2D phases is nearly quenched, while the same mechanism for surface-coordinating ligands is greatly improved, compared to the free ligands. The improvement originates from an energy transfer from perovskite to azobenzene, which is strongly distance-dependent. This study provides evidence for the photoswitching of azobenzenes as ligands of hybrid perovskites, which depends on the spacing between the chromophore and the perovskite phase.

Dataset Information

Synthesis and testing of the first azobenzene mannobioside as photoswitchable ligand for the bacterial lectin FimH.

Publications

Synthesis and testing of the first azobenzene mannobioside as photoswitchable ligand for the bacterial lectin FimH.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets