Fluorescent-Labeled Lipophilic Analogues of Serotonin, Dopamine, and Acetylcholine: Synthesis, Mass Spectrometry, and Biological Activity

Fragmentation patterns of boron‐dipyrromethene (BODIPY) dyes by electrospray ionization high‐resolution tandem mass spectrometry

“…Similar challenges occurred when the action of ROS was studied by the above mentioned ratiometric probes; the high cost of the commercial labelling molecules did not allow the generation of sufficient amounts of product for reliable structural elucidation. As a result, researchers switched to mass spectrometry (MS) for characterization purposes …”

“…Until today, only very few studies have focused on the MS/MS behaviour of BODIPY dyes. Most of these investigations have applied CID to the analysis of commercial BODIPYs as well as structural characterization of labelled ROS products . However, due to the insufficient mass resolving power of the ion trap mass spectrometer used in those studies, only product ions from side‐chain losses were identified; superimposed fragmentation reactions from parallel [M] +• and [M+H] + species were never reported.…”

“…As a result, researchers switched to mass spectrometry (MS) for characterization purposes. [18][19][20][21] High-resolution mass spectrometry (HRMS) is a powerful method for determining elemental compositions from measured accurate masses. In addition, structural information can be deduced from tandem mass spectrometry (MS/MS) experiments.…”

“…Most of these investigations have applied CID to the analysis of commercial BODIPYs as well as structural characterization of labelled ROS products. [18][19][20][21] However, due to the insufficient mass resolving power of the ion trap mass spectrometer used in those studies, only product ions from side-chain losses were identified; superimposed fragmentation reactions from parallel [M] +• and [M+H] + species were never reported. Here, both triple quadrupole and Fourier transform ion cyclotron resonance (FTICR) mass spectrometry were applied to study the CID fragmentation patterns of ten BODIPY dyes ( Table 1).…”

Fluorescent mimics of 5-hydroxytryptamine based on N-alkylated derivatives of 6-hydroxycarbostyril

“…16 Fluorescently labeled neurotransmitters have been reported, yet they either are limited to reporting the presence of cell surface receptors 17 or exhibit activity markedly different from the natural substrate. 18 We have synthesized a series of fluorescent analogs of 5HT as novel probes for the serotonergic system, and explored their optical properties and behavior in vitro. In screening their activity against cultured neurons and astroglia in the presence and absence of the SRI clomipramine, we have determined that two probes, 1 and 4, may function as fluorescent analogs of 5HT.…”