Determination of N-methyl-1,3-propanediamine in bovine muscle by liquid chromatography with triple quadrupole and ion trap tandem mass spectrometry detection.

Morantel, pyrantel and their drug-related metabolites in food of animal-origin are regulated as sum of residues which may be hydrolysed to N-methyl-1,3-propanediamine (NMPA). In this study, an isotope dilution liquid chromatography tandem mass spectrometry (LC-MS/MS) method with pentafluoropropionic acid anhydride (PFPA) derivatization was developed for the determination of NMPA in bovine muscle. A stable isotope labeled internal standard N-methyl-d(3)-3,3'-d(2)-propane-1,3-diamine (NMPA-d(5)) was synthesized as internal standard. NMPA was derivatized with PFPA to form an N,N'-bis (pentafluoroacyl) derivative (NMPA-PFPA) and analyzed by liquid chromatography triple quadrupole mass spectrometry (LC-QqQ-MS/MS) and liquid chromatography ion trap mass spectrometry (LC-IT-MS/MS) using negative ion electrospray ionization (ESI). Chromatographic behavior of several perfluorocarboxylic acid anhydride derivatives of NMPA and other structurally related diamines on C-18 and perfluorophenyl (PFP) columns was studied. Conversion of the parent drugs to NMPA under various hydrolysis conditions was evaluated. In addition, comparison of the matrix effect and linearity with isotopically labeled internal standard (I.S.) and analogous I.S. were performed and investigated. The method was validated using fortified bovine muscle samples. The apparent recovery (obtained after correction with an isotopically labeled I.S.) was between 89% and 97% and repeatability was less than 10%. The lowest LOD and LOQ (0.42 and 1.39μg/kg, respectively) were obtained with LC-QqQ-MS/MS.

[1]  Comparative study of hydrocarbon, fluorocarbon, and aromatic bonded RP-HPLC stationary phases by linear solvation energy relationships. , 1999 .

[2]  P. Persson,et al.  Determination of 4,4'-methylenedianiline in hydrolysed human urine by micro liquid chromatography with ultraviolet detection. , 1992, Journal of chromatography.

[3]  J. Van Loco,et al.  Validation of a method for the detection and confirmation of nitroimidazoles and the corresponding hydroxy metabolites in pig plasma by high performance liquid chromatography-tandem mass spectrometry. , 2007, Analytica chimica acta.

[4]  G. Knupp,et al.  Identification and Structural Elucidation of Corrosion Inhibiting Long-Chain N-1-Alkyl-1,3-propanediamines by GC–MS , 2009 .

[5]  M. Longo,et al.  Determination of aromatic amines at trace levels by derivatization with heptafluorobutyric anhydride and gas chromatography-electron-capture negative-ion chemical ionization mass spectrometry , 1996 .

[6]  A. Monro,et al.  The comparative metabolism of pyrantel in five species. , 1972, Journal of the science of food and agriculture.

[7]  L. Alhonen,et al.  Synthesis of novel deuterium labelled derivatives of N-alkylated polyamines , 2009 .

[8]  P. Plaza-Bolaños,et al.  Comparison of tandem-in-space and tandem-in-time mass spectrometry in gas chromatography determination of pesticides: application to simple and complex food samples. , 2008, Journal of chromatography. A.

[9]  P. Stepnowski,et al.  Retention mechanism of selected ionic liquids on a pentafluorophenylpropyl polar phase: investigation using RP-HPLC. , 2009, Journal of chromatographic science.

[10]  D. Karlsson,et al.  Extractable organic compounds in polyurethane foam with special reference to aromatic amines and derivatives thereof , 2004 .

[11]  G. Bartolucci,et al.  Liquid chromatography tandem mass spectrometric quantitation of sulfamethazine and its metabolites: direct analysis of swine urine by triple quadrupole and by ion trap mass spectrometry. , 2000, Rapid communications in mass spectrometry : RCM.

[12]  G. Knupp,et al.  Identification of corrosion inhibiting long-chain primary alkyl amines by gas chromatography and gas chromatography–mass spectrometry , 2007 .

[13]  G. Skarping,et al.  Determination of 4,4'-methylenedianiline in hydrolysed human urine using liquid chromatography with UV detection and peak identification by absorbance ratio. , 1990, Journal of chromatography.

[14]  A. Garnier-Suillerot,et al.  Impact of the carbon chain length of novel platinum complexes derived from N-alkyl-propanediamines on their cytotoxic activity and cellular uptake. , 2008, Journal of inorganic biochemistry.

[15]  P. Petersson,et al.  Chromatographic classification and comparison of commercially available perfluorinated stationary phases for reversed‐phase liquid chromatography using Principal Component Analysis , 2003 .

[16]  Yolanda Picó,et al.  Comparison of liquid chromatography using triple quadrupole and quadrupole ion trap mass analyzers to determine pesticide residues in oranges. , 2005, Journal of chromatography. A.

[17]  Fernanda Galgano,et al.  Role of biogenic amines as index of freshness in beef meat packed with different biopolymeric materials , 2009 .

[18]  Claudia Ruiz-Capillas,et al.  Biogenic Amines in Meat and Meat Products , 2005, Critical reviews in food science and nutrition.

[19]  Johanna Smeyers-Verbeke,et al.  Handbook of Chemometrics and Qualimetrics: Part A , 1997 .

[20]  B. Matuszewski,et al.  Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS. , 2003, Analytical chemistry.

[21]  D. Durden,et al.  A comparison of the gas chromatographic and mass spectrometric properties of the pentafluoropropionyl and heptafluorobutyryl derivatives of the methyl, trifluoroethyl, pentafluoropropyl and hexafluoroisopropyl esters of twelve acidic metabolites of biogenic amines. , 1987, Biomedical & environmental mass spectrometry.

[22]  L. Leuthold,et al.  Triple quadrupole linear ion trap mass spectrometer for the analysis of small molecules and macromolecules. , 2004, Journal of mass spectrometry : JMS.

[23]  H. Tinnerberg,et al.  Biological monitoring of hexamethylene- and isophorone-diisocyanate by the determination of hexamethylene- and isophorone-diamine in hydrolysed urine using liquid chromatography and mass spectrometry. , 1994, The Analyst.

[24]  M. T. Veciana-Nogués,et al.  Biogenic amine and polyamine contents in meat and meat products , 1997 .

[25]  D. Karlsson,et al.  Determination of amines as pentafluoropropionic acid anhydride derivatives in biological samples using liquid chromatography and tandem mass spectrometry. , 2004, The Analyst.

[26]  P. Worsfold,et al.  Separation and detection of siderophores produced by marine bacterioplankton using high-performance liquid chromatography with electrospray ionization mass spectrometry. , 2003, Analytical chemistry.

[27]  M. Fountoulakis,et al.  Hydrolysis and amino acid composition analysis of proteins , 1998 .

[28]  M. Dalene,et al.  Liquid chromatography and mass spectrometry determination of aromatic amines in hydrolysed urine from workers exposed to thermal degradation products of polyurethane , 1994 .

[29]  B. Jönsson,et al.  Analysis of 3,5-dichloroaniline as a biomarker of vinclozolin and iprodione in human urine using liquid chromatography/triple quadrupole mass spectrometry. , 2007, Rapid communications in mass spectrometry : RCM.

[30]  R. Yost,et al.  Tandem-in-space and tandem-in-time mass spectrometry: triple quadrupoles and quadrupole ion traps , 1990 .

[31]  P. de Backer,et al.  Quantitative determination of dihydrostreptomycin in bovine tissues and milk by liquid chromatography-electrospray ionization-tandem mass spectrometry. , 2007, Journal of mass spectrometry : JMS.