906533-44-6Relevant articles and documents
Fluorescence phenomena in nerve-labeling styryl-type dyes
Siclovan, Tiberiu M.,Zhang, Rong,Cotero, Victoria,Bajaj, Anshika,Dylov, Dmitry V.,Yazdanfar, Siavash,Carter, Randall L.,Hehir, Cristina A.Tan,Natarajan, Arunkumar
, p. 104 - 116 (2016)
Several classes of diversely substituted styryl type dyes have been synthesized with the goal of extending their expected fluorescent properties as much toward red as possible given the constraint that they maintain drug-like properties and retain high affinity binding to their biological target. We report on the synthesis, optical properties of a series of styryl dyes (d1-d14), and the anomalous photophysical behavior of several of these donor-acceptor pairs separated by long conjugated π-systems (d7-d10). We further describe an unusual dual emission behavior with two distinct ground state conformers which could be individually excited to locally excited (LE) and twisted intramolecular charge transfer (TICT) excited state in push-pull dye systems (d7, d9 and d10). Additionally, unexpected emission behavior in dye systems d7 and d8 wherein the amino-derivative d7 displayed a dual emission in polar medium while the N,N-dimethyl derivative d8 and other methylated derivatives d12-d14 showed only LE emission but did not show any TICT emission. Based on photophysical and nerve binding studies, we down selected compounds that exhibited the most robust fluorescent staining of nerve tissue sections. These dyes (d7, d9, and d10) were subsequently selected for in vivo fluorescence imaging studies in rodents using the small animal multispectral imaging instrument and the dual-mode laparoscopic instrument developed in-house.
Polyfluorinated bis-styrylbenzenes as amyloid-β plaque binding ligands
Nabuurs, Rob J.A.,Kapoerchan, Varsha V.,Metaxas, Athanasios,De Jongh, Sanne,De Backer, Maaike,Welling, Mick M.,Jiskoot, Wim,Windhorst, Albert D.,Overkleeft, Hermen S.,Van Buchem, Mark A.,Overhand, Mark,Van Der Weerd, Louise
, p. 2469 - 2481 (2014/05/06)
Detection of cerebral β-amyloid (Aβ) by targeted contrast agents remains of great interest to aid the in vivo diagnosis of Alzheimer's disease (AD). Bis-styrylbenzenes have been previously reported as potential Aβ imaging agents. To further explore their potency as 19F MRI contrast agents we synthetized several novel fluorinated bis-styrylbenzenes and studied their fluorescent properties and amyloid-β binding characteristics. The compounds showed a high affinity for Aβ plaques on murine and human brain sections. Interestingly, competitive binding experiments demonstrated that they bound to a different binding site than chrysamine G. Despite their high logP values, many bis-styrylbenzenes were able to enter the brain and label murine amyloid in vivo. Unfortunately initial post-mortem 19F NMR studies showed that these compounds as yet do not warrant further MRI studies due to the reduction of the 19F signal in the environment of the brain.
