225531-75-9Relevant academic research and scientific papers
Development of photoswitchable estrogen receptor ligands
Demizu, Yosuke,Fukuhara, Kiyoshi,Misawa, Takashi,Tanaka, Masakazu,Tsuchiya, Keisuke,Tsuji, Genichiro,Umeno, Tomohiro,Yokoo, Hidetomo
, p. 398 - 402 (2020/05/14)
Photopharmacology has attracted attention as an approach for the development of novel therapeutics because it allows regulation of the bioactivity of compounds based on their conformational change by photo-irradiation. Previously, we have reported several types of selective estrogen receptor (ER) modulators based on diphenylmethane skeleton. To develop novel photopharmacological reagents, we designed and synthesized a set of ER ligands based on azobenzene skeleton, which can switch its conformation following UV irradiation. Our results showed that after UV irradiation, the Z-form of the synthesized compound 9 interacted with ERα, with a KD value of 2.5μM, whereas the E-form of compound 9 did not bind ability to ERα at 10μM.
Photocontrol of Antibacterial Activity: Shifting from UV to Red Light Activation
Wegener, Michael,Hansen, Mickel J.,Driessen, Arnold J. M.,Szymanski, Wiktor,Feringa, Ben L.
, p. 17979 - 17986 (2017/12/26)
The field of photopharmacology aims to introduce smart drugs that, through the incorporation of molecular photoswitches, allow for the remote spatial and temporal control of bioactivity by light. This concept could be particularly beneficial in the treatment of bacterial infections, by reducing the systemic and environmental side effects of antibiotics. A major concern in the realization of such light-responsive drugs is the wavelength of the light that is applied. Studies on the photocontrol of biologically active agents mostly rely on UV light, which is cytotoxic and poorly suited for tissue penetration. In our efforts to develop photoswitchable antibiotics, we introduce here antibacterial agents whose activity can be controlled by visible light, while getting into the therapeutic window. For that purpose, a UV-light-responsive core structure based on diaminopyrimidines with suitable antibacterial properties was identified. Subsequent modification of an azobenzene photoswitch moiety led to structures that allowed us to control their activity against Escherichia coli in both directions with light in the visible region. For the first time, full in situ photocontrol of antibacterial activity in the presence of bacteria was attained with green and violet light. Most remarkably, one of the diaminopyrimidines revealed an at least 8-fold difference in activity before and after irradiation with red light at 652 nm, showcasing the effective "activation" of a biological agent otherwise inactive within the investigated concentration range, and doing so with red light in the therapeutic window.
Azobenzene-porphyrins
Hunter,Hunter, Christopher A.,Sarson,Sarson, Luke D.
, p. 699 - 702 (2007/10/02)
A series of covalently-connected azobenzene-porphyrin derivatives have been synthesised and their photochemical properties investigated. The photochemistry of the porphyrin components is essentially unaltered, but photochemical isomerisation of the azobenzene components can not be detected.
