Detection of 28 neurotransmitters and related compounds in biological fluids by liquid chromatography/tandem mass spectrometry

Bourcier, Sophie; Benoist, Jean‐François; Clerc, Frédèric; Rigal, Odile; Taghi, Méryam; Hoppilliard, Y.

doi:10.1002/rcm.2459

Cited by 65 publications

(52 citation statements)

References 32 publications

(44 reference statements)

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“…11,12 The facile elimination of NH 3 upon collision-induced dissociation 11,12 is compatible with preferential protonation at the terminal amino group of the ethyl side chain, as predicted by theory. 5 The proton affinity calculated at the B3LYP/6-31G(d) level amounts to 940 kJ mol À1 , 13 however no experimental determination of this quantity appears to be available [13][14][15] for comparison to 16 In these studies, protonation of the neurotransmitter molecule is accomplished by ionization-induced intracluster proton transfer occurring in a hydrogen-bonded phenol-neurotransmitter cluster generated in a molecular beam.…”

Section: Introductionsupporting

confidence: 61%

“…11,12 However, the fragment with m = 119 u was only observed in the CID spectra at 35 eV collision energy. 11 As outlined above, the analysis of the IR action spectra monitored in the 137 and 91/119 u fragment channels indicates that photoinduced fragmentation occurs in a sequential fashion (i.e., 154 u -137 u -91/119 u). A similar process was recently observed for IRMPD of protonated benzaldehyde.…”

Section: Fragmentation Processmentioning

confidence: 99%

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Infrared spectra of protonated neurotransmitters: dopamine

Lagutschenkov

Langer

Berden

et al. 2011

Phys. Chem. Chem. Phys.

108

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The infrared (IR) spectrum of the isolated protonated neurotransmitter dopamine was recorded in the fingerprint range (570-1880 cm À1) by means of IR multiple photon dissociation (IRMPD) spectroscopy. The spectrum was obtained in a Fourier transform ion cyclotron resonance mass spectrometer equipped with an electrospray ionization source, which was coupled to a free electron laser (FEL). The spectroscopic studies are complemented by quantum chemical calculations at the B3LYP and MP2 levels of theory using the cc-pVDZ basis set. Several low-energy isomers with protonation occurring at the amino group are predicted in the energy range 0-50 kJ mol À1. Good agreement between the measured IRMPD spectrum and the calculated linear absorption spectra is observed for the two gauche conformers lowest in energy (DE) and free energy (DG) at both levels of theory, denoted gÀ1 and g+1. Minor contributions of higher lying gauche isomers cannot be ruled out spectroscopically but their calculated energies suggest only minor population in the sampled ion cloud. In all these gauche structures, one of the three protons of the ammonium group is pointing toward the catechol subunit, thereby maximizing the intramolecular NH-p interaction of the positive charge with the aromatic ring. In total, 16 distinct vibrational bands are observed in the IRMPD spectrum and assigned to individual normal modes of the energetically most stable gÀ1 conformer, with deviations of less than 24 cm À1 (average 11 cm À1) between measured and calculated frequencies. Comparison with neutral dopamine reveals the effects of protonation on the geometric and electronic structure.

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Section: Introductionsupporting

confidence: 61%

Section: Fragmentation Processmentioning

confidence: 99%

Infrared spectra of protonated neurotransmitters: dopamine

Lagutschenkov

Langer

Berden

et al. 2011

Phys. Chem. Chem. Phys.

108

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“….loss of oxygen, or oxygen and a proton." However, this is not consistent with reported fragmentation patterns for the parent molecule (43,44).…”

contrasting

confidence: 56%

Importance of single molecular determinants in the fidelity of expanded genetic codes

Antonczak¹,

Šimová²,

Yonemoto³

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

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The site-selective encoding of noncanonical amino acids (NAAs) is a powerful technique for the installation of novel chemical functional groups in proteins. This is often achieved by recoding a stop codon and requires two additional components: an evolved aminoacyl tRNA synthetase (AARS) and a cognate tRNA. Analysis of the most successful AARSs reveals common characteristics. The highest fidelity NAA systems derived from the Methanocaldococcus jannaschii tyrosyl AARS feature specific mutations to two residues reported to interact with the hydroxyl group of the substrate tyrosine. We demonstrate that the restoration of just one of these determinants for amino acid specificity results in the loss of fidelity as the evolved AARSs become noticeably promiscuous. These results offer a partial explanation of a recently retracted strategy for the synthesis of glycoproteins. Similarly, we reinvestigated a tryptophanyl AARS reported to allow the site-selective incorporation of 5-hydroxy tryptophan within mammalian cells. In multiple experiments, the enzyme displayed elements of promiscuity despite its previous characterization as a high fidelity enzyme. Given the many similarities of the TyrRSs and TrpRSs reevaluated here, our findings can be largely combined, and in doing so they reinforce the long-established central dogma regarding the molecular basis by which these enzymes contribute to the fidelity of translation. Thus, our view is that the central claims of fidelity reported in several NAA systems remain unproven and unprecedented. directed evolution | protein engineering

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“…Currently, a combination of high-performance liquid chromatography and tandem mass spectrometry (HPLC-MS-MS) has been developed as a powerful modern analytical technique that merges the resolving power of HPLC with the detection specificity and potentially low detection limits of tandem MS. Several HPLC-MS methods have been developed for the determination of GABA in biological fluids by combining chromatography with atmospheric pressure chemical ionization mass spectrometry, capillary liquid chromatography and MS-MS, as well as LC-MS-MS (Ma et al, 1999;Song et al, 2005;Bourcier et al, 2006). The only published study of the brain-penetrating properties of phenibut did not describe technical details and failed to quantify the concentration of the drug in adult rat brains (Khaunina and Maslova, 1968).…”

Section: Introductionmentioning

confidence: 97%

Quantitative analysis of phenibut in rat brain tissue extracts by liquid chromatography–tandem mass spectrometry

Grı̄nberga

Zvejniece

Liepinsh

et al. 2008

Biomedical Chromatography

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Phenibut (3-phenyl-4-aminobutyric acid) is a gamma-aminobutyric acid mimetic drug, which is used clinically as a mood elevator and tranquilizer. In the present work, a rapid, selective and sensitive liquid chromatography-tandem mass spectrometry method for quantification of phenibut in biological matrices has been developed. The method is based on protein precipitation with acidic acetonitrile followed by isocratic chromatographic separation using acetonitrile-formic acid (0.1% in water; 8:92, v/v) mobile phase on a reversed-phase column. Detection of the analyte was performed by electrospray ionization mass spectrometry in multiple reaction monitoring mode with the precursor-to-product ion transition m/z 180.3 --> m/z 117.2. The calibration curve was linear over the concentration range 50-2000 ng/mL. The lower limit of quantification for phenibut in rat brain extracts was 50 ng/mL. Acceptable precision and accuracy were obtained over the whole concentration range. The validated method was successfully applied in a pharmacological study to analyze phenibut concentration in rat brain tissue extract samples.

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Detection of 28 neurotransmitters and related compounds in biological fluids by liquid chromatography/tandem mass spectrometry

Cited by 65 publications

References 32 publications

Infrared spectra of protonated neurotransmitters: dopamine

Infrared spectra of protonated neurotransmitters: dopamine

Importance of single molecular determinants in the fidelity of expanded genetic codes

Quantitative analysis of phenibut in rat brain tissue extracts by liquid chromatography–tandem mass spectrometry

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