36092-33-8Relevant academic research and scientific papers
Synthesis, dual fluorescence, and fluoroionophoric behavior of dipyridylaminomethylstilbenes
Yang, Jye-Shane,Lin, Yan-Duo,Chang, Ya-Ho,Wang, Shin-Shin
, p. 6066 - 6073 (2007/10/03)
The synthesis, dual fluorescence, and fluoroionophoric behavior of two donor-σ spacer-acceptor (D-s-A) compounds, trans-4-(N,N-bis(2-pyridyl) amino)methylstilbene (1H) and trans-4-(N,N-bis(2-pyridyl)amino)methyl-4′- cyanostilbene (1CN), are reported and compared to that of trans-4-(N,N-bis(2- pyridyl)amino)methyl-4′-(N,N-dimethylammo)stilbene (1DPA). To gain insights into the dual fluorescence properties for 1H and 1CN in polar but not in nonpolar solvents, model compounds resulting from a replacement of the stilbene group by alkyl (2R) or xylyl (2X) groups or from a replacement of the dipyridylamino (dpa) group by dianisoleamino (3AA), diethylamino (SEE), methylanilino (3MP), or diphenylamino (3PP) groups also have been investigated. In addition to 1H and 1CN, all four compounds of 3 display dual fluorescence. The locally excited (LE) fluorescence mainly results from the stilbene group and the ICT fluorescence from the through-bond interactions between the amino donor and the stilbene acceptors. In the presence of transition metal ions such as Zn(II), Ni(II), Cu(II), and Cd(II), the ICT processes are switched from dpa → stilbene (A) in 1H and 1CN to stilbene (D) → dpa/metal ion (A) in their complexes. Whereas the ICT states for the complexes are generally nonfluorescent, an exception was found for the case of 1H/Zn(II). As a result, substituent-dependent fluoroionophoric behavior has been demonstrated by 1H, 1CN, and 1DPA in response to Zn(II).
Synthesis and characterization of fluorescent ligands for the norepinephrine transporter: Potential neuroblastoma imaging agents
Hadrich, Dirk,Berthold, Frank,Steckhan, Eberhard,B?nisch, Heinz
, p. 3101 - 3108 (2007/10/03)
Radiolabeled m-iodobenzylguanidine (MIBG) is a tumor-seeking radioactive drug used in the diagnosis and treatment of pheochromocytomas and neuroblastomas. It is transported into the tumor cells by the neuronal norepinephrine (NE) transporter (NET) which is expressed in almost all neuroblastoma cells. Here, we describe the synthesis and some pharmacological properties of a series of fluorescent compounds structurally related to the NET substrate, MIBG, or to the NET inhibitors, (-)-(2R,3S)-cocaine and nisoxetine. Three of 10 synthesized fluorescent compounds, 1-(1- naphthylmethyl)guanidinium sulfate (1), 1-[2-(dibenz[b,f]azepin-5- yl)ethyl]guanidinium sulfate (2), and (2R,3S)-2β-ethoxycarbonyl-3β-tropanyl 5-(dimethylamino)naphthalene-1-sulfonate (6), exhibited high affinity (IC50 about 50 nM) for the NET. The nisoxetine derivatives 8 (rac-N-[(3- methylamino-1-phenyl)propyl]-5-(dimethylamino)-1-naphthalene-sulfonamide) and 9 (rac-4-[(3-methylamino-1-phenyl)propyl]amino-7-nitro-2,1,3-benzoxadiazole) and especially the guanidine derivative 4 (1-[4-(4-phenyl-l,3- butadienyl)benzyl]guanidinium sulfate) which are characterized by intermediate affinity for the NET (IC50 370-850 nM) caused significant and nisoxetine-sensitive cell fluorescence. At least the guanidine derivative 4 might represent a potentially useful agent for imaging of neuroblastoma cells.
