17104-27-7Relevant articles and documents
Self-assembly of Fluorescent Dehydroberberine Enhances Mitochondria-Dependent Antitumor Efficacy
An, Ruibing,Gu, Zhanni,Sun, Haifeng,Hu, Yuxuan,Yan, Runqi,Ye, Deju,Liu, Hong
, p. 9812 - 9819 (2018)
Selective imaging and inducing mitochondrial dysfunction in tumor cells using mitochondria-targeting probes has become as a promising approach for cancer diagnosis and therapy. Here, we report the design of a fluorescent berberine analog, dehydroberberine (DH-BBR), as a new mitochondria-targeting probe capable of self-assembling into monodisperse organic nanoparticles (DTNPs) upon integration with a lipophilic counter anion, allowing for enhanced fluorescence imaging and treatment of tumors in living mice. X-ray crystallography revealed that the self-assembly process was attributed to a synergy of different molecular interactions, including π–π stacking, O???π interaction and electrostatic interaction between DH-BBR and counter anions. We demonstrated that DTNPs could efficiently enter tumor tissue following intravenous injection and enhance mitochondrial delivery of DH-BBR via an electrostatic interaction driven anion exchange process. Selective accumulation in the mitochondria capable of emitting strong fluorescence and causing mitochondrial dysfunction was achieved, enabling efficient inhibition of tumor growth in living mice. This study demonstrates promise for applying lipophilic anions to control molecular self-assembly and tune antitumor activity of mitochondria-targeting probes, which can facilitate to improve cancer treatment in vivo.
A very mild access to 3,4-dihydroisoquinolines using triphenyl phosphite-bromine-mediated bischler-napieralski-type cyclization
Vaccari, Daniele,Davoli, Paolo,Ori, Claudia,Spaggiari, Alberto,Prati, Fabio
scheme or table, p. 2807 - 2810 (2009/05/07)
Substituted β-phenylethylamides undergo smooth intramolecular cyclization to 3,4-dihydroisoquinolines in good to excellent yields when treated with bromotriphenoxyphosphonium bromide at -60°C in dichloromethane in the presence of triethylamine. The reaction proceeds under the mildest conditions ever reported for Bischler-Napieralski-type cyclizations. When chlorotriphenoxyphosphonium choride is used, low yields are obtained instead. Georg Thieme Verlag Stuttgart.
The E.S.R. Spectra of Cation Radicals Derived from Phenethyltetrahydroisoquinoline Ethers and Model Compounds
Hewgill, Frank R.,Pass, Michael C.
, p. 555 - 563 (2007/10/02)
Cation radicals derived from the title compounds by oxidation with thallium tristrifluoroacetate have been characterized.The structures assigned to these radicals suggest that initial oxidation occures at the phenethyl ring in the compounds examined.Oxidation of homolaudanosine in this way gave the expected homoaporphine.
