4800-57-1Relevant academic research and scientific papers
Evaluation of the antidepressant therapeutic potential of isocyanine and pseudoisocyanine analogues of the organic cation decynium-22
Krause-Heuer, Anwen M.,Fraser-Spears, Rheaclare,Dobrowolski, Jeremy C.,Ashford, Mark E.,Wyatt, Naomi A.,Roberts, Maxine P.,Gould, Georgianna G.,Cheah, Wai-Ching,Ng, Clarissa K.L.,Bhadbhade, Mohan,Zhang, Bo,Greguric, Ivan,Wheate, Nial J.,Kumar, Naresh,Koek, Wouter,Callaghan, Paul D.,Daws, Lynette C.,Fraser, Benjamin H.
, p. 476 - 487 (2017/06/20)
Herein we describe the synthesis and evaluation of antidepressant properties of seven analogues (1–7) of the low affinity/high capacity transporter blocker decynium-22 (D-22). All analogues (1–7) were synthesized via base promoted coupling reactions between N-alkylated-2-methylquinolinium iodides or N-alkylated-4-methylquinolinium iodides and electrophilic N-alkylated-2-iodoquinolinium iodides. All final compounds were purified by re-crystallization or preparative HPLC and initial evaluation studies included; 1) screening for in vitro α1-adrenoceptor activity (a property that can lead to unwanted side-effects), 2) measuring antidepressant-like activity in a mouse tail suspension test (TST), and 3) measuring effects upon mouse locomotion. The results showed some analogues have lower affinities at α1-adrenoceptors compared to D-22 and showed antidepressant-like activity without the need for co-administration of SSRIs. Additionally, many analogues did not affect mouse locomotion to the same extent as D-22. Plans for additional evaluations of these promising analogues, including measurement of antidepressant-like activity with co-administration of selective serotonin re-uptake inhibitors (SSRIs), are outlined.
New cyanine-oligonucleotide conjugates: Relationships between chemical structures and properties
Lartia, Remy,Asseline, Ulysse
, p. 2270 - 2281 (2008/02/03)
Because the influence of the chemical structure of monomethine cyanine-oligo-2′-deoxyribonudeotide (ODN) conjugates on their binding and fluorescence properties has remained largely undetermined, we synthesized and studied a wide range of conjugates with various structural patterns. Different cyanine dyes such as thiocyanine, quinocyanine, and thiazole orange isomers were obtained. In the case of unsymmetrical cyanines. the linker was attached to either the quinoline or the benzothiazole nucleus. The influence of the ODN counterpart was evaluated by linking the cyanines to the 5'-end or to an internucleotidic phosphate. In the first case, the influence of neighboring nucleic bases was studied, whereas in the second, the stereochemical configuration at the phosphorus atom bearing the cyanine was investigated. We report here on relationships between the structures of the dyes and conjugates and some of their properties, such as the stability and fluorescence changes observed on their hybridization with the target sequence. This study provides useful information towards the design of ODN-cyanine conjugates.
Chiral Polymethine Dyes, III. Synthesis and Spectroscopic Properties of an Unsymmetrical, Chiral Monomethine Cyanine Dye with Thiazolyl and Quinolinyl End Group
Reichardt, Christian,Budnik, Ulrich
, p. 927 - 930 (2007/10/02)
The synthesis of the unsymmetrical monomethine cyanine dye 6 in its monochiral (6a, b) and isochiral form (6c), first realized by Goetze in 1938, has been significantly improved and its spectroscopic properties have been studied.According to the synthetic
