On-line HPLC-tandem mass spectrometry structural characterization of case-associated contaminants of L-tryptophan implicated with the onset of eosinophilia myalgia syndrome

Toxicology Letters

Volumn 99, Issue 2, 1998, Pages 139-150

  Williamson, Brian L ^a   Johnson, Kenneth L ^a   Tomlinson, Andy J ^a   Gleich, Gerald J ^a   Naylor, Stephen ^a  

^a MAYO CLINIC   (United States)

Author keywords

Case associated contaminants; Eosinophilia myalgia syndrome; HPLC tandem mass spectrometry; L tryptophan

Indexed keywords

TRYPTOPHAN;

ARTICLE; DRUG CONTAMINATION; DRUG IDENTIFICATION; EOSINOPHILIA MYALGIA SYNDROME; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG CONTAMINATION; EOSINOPHILIA-MYALGIA SYNDROME; HUMANS; MASS SPECTROMETRY; TRYPTOPHAN;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0032428208     PISSN: 03784274     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-4274(98)00223-9     Document Type: Article

References (40)

1. Belongia E.A., Hedberg C.W., Gleich G.J. et al. An investigation of the cause of the eosinophilia-myalgia syndrome associated with tryptophan use. New Engl. J. Med. 323:1990;357-365.
2. Busch K.L., Glish G.L., McLuckey S.A. Mass Spectrometry/Mass Spectrometry, Techniques and Applications in Tandem Mass Spectrometry. 1988;VCH, New York.
3. Eidson M., Philen R.M., Sewell C.M., Voorhees R., Kilbourne E.M. L-tryptophan and eosinophilia-myalgia syndrome in New Mexico. Lancet. 335:1990;645-648.
4. Fasman G.D. Practical Handbook of Biochemistry and Molecular Biology. 1989;CRC Press, Boca Raton, FL.
5. Gelpi E. Biomedical and biochemical applications of liquid chromatography-mass spectrometry. J. Chromatogr. A 703:1995;59-80.
6. Goda Y., Suzuki J., Maitani T, Yoshihira K., Takeda M., Uchiyama M. 3-Anilino-L-alanine, structural determination of UV-5, a contaminant in EMS-associated L-tryptophan samples. Chem. Pharm. Bull. (Tokyo). 40:1992;2236-2238.
7. Gutsche B., Herderich M. High performance liquid chromatography electrospray ionization-tandem mass spectrometry (HPLC-ESI-MS-MS) for the analysis of 1,2,3,4-tetrahydro-β-carboline derivatives. J. Chromatogr. A 767:1997;101-106.
8. Hatch D.L., Garona J.E., Goldman L.R., Waller K.O. Persistent eosinophilia in an infant with probable intrauterine exposure to L-tryptophan-containing supplements. Pediatrics. 88:1991;810-813.
9. Hill R.H. Jr., Caudill S.P., Philen R.M. et al. Contaminants in L-tryptophan associated with eosinophilia myalgia syndrome. Arch. Environ. Contam. Toxicol. 25:1993;134-142.
10. Kilbourne E.M., Posada de la Paz M., Borda I.A., Ruiz-Navarro M.D., Philen R.M., Falk H. Toxic oil syndrome: a current clinical and epidemiologic summary, including comparisons with the eosinophilia-myalgia syndrome. J. Am. Coll. Cardiol. 18:1991;711-717.
11. Kilbourne E.M. Eosinophilia-myalgia syndrome: coming to grips with a new illness. Epidemiol. Rev. 14:1992;16-36.
12. Lampert A., Joly P., Thomine E., Ortoli J.C., Lauret P. Scleroderma-like syndrome with bullous morphea during treatment with 5-hydroxytryptophan, carbidopa and flunitrazepam. Ann. Dermatol. Venereol. 119:1992;209-211.
13. Leclercq P.A., Desiderio D.M. Chemical ionization mass spectra of amino acids and derivatives: occurrence and fragmentation of ion-molecule reaction products. Org. Mass Spectrom. 7:1973;515-533.
14. Mayeno A.N., Lin F., Foote C.S. et al. Characterization of 'Peak E', a novel amino acid associated with eosinophilia-myalgia syndrome. Science. 250:1990;1707-1708.
15. Mayeno A.N., Belongia E.A., Lin F., Lundy S.K., Gleich G.J. 3-(Phenylamino)alanine, a novel aniline-derived amino acid associated with the eosinophilia-myalagia syndrome: a link to the toxic oil syndrome? Mayo Clin. Proc. 67:1992;1134-1139.
16. Mayeno A.N., Benson L.M., Naylor S., Colberg-Beers M., Puchalski J.T., Gleich G.J. Biotransformation of 3-(phenylamino)-1, 2-propanediol to 3-(phenylamino)alanine: A chemical link between toxic oil syndrome and eosinophilia-myalgia syndrome. Chem. Res. Toxicol. 8:1995;911-916.
17. McLafferty F.W. Tandem Mass Spectrometry. 1993;Wiley, New York.
18. Michelson D., Page S.W., Casey R. et al. An eosinophilia-myalgia syndrome related disorder associated with exposure to L-5-hydroxytryptophan. J. Rheumatol. 21:1994;1261-2265.
19. Milne G.W., Axenrod T., Fales H.M. Chemical ionization mass spectrometry of complex molecules: IV amino acids. J. Am. Chem. Soc. 92:1970;5170-5175.
20. Muller A., Busker E., Gunther K., Hoppe B. Characterization of byproducts in L-tryptophan. Bioforum. 14:1991;350-354.
21. Niessen W.M.A. Liquid chromatograph-mass spectrometry: general principles and instrumentation. J. Chromatogr. A 703:1995;37-57.
22. Philen R.M., Hill R.H. Jr., Flanders W.D. et al. Tryptophan contaminants associated with eosinophilia-myalgia syndrome. Am. J. Epidemiol. 138:1993;154-159.
23. Sato F., Hagiwara Y., Kawase Y. Subchronic toxicity of 3-phenylamino alanine, an impurity in L-tryptophan reported to be associated to be associated with eosinophilia-myalgia syndrome. Arch. Toxicol. 69:1995;444-449.
24. Savige W.E., Fontana A. A novel synthesis of 2-thioether derivatives of tryptophan: covalent binding of tryptophan to cysteine sulfhydryl groups in peptides and proteins. Int. J. Pept. Protein Res. 15:1980;102-112.
25. Silver R.M. Eosinophilia-myalgia syndrome, toxic oil syndrome, and diffuse faciitis with eosinophilia. Curr. Opin. Rheumatol. 4:1992;851-856.
26. Silver R.M. The eosinophilia-myalgia syndrome. Clin. Dermatol. 12:1994;457-465.
27. Slutsker L., Hoesly F.C., Miller L., Williams L.P., Watson J.C., Fleming D.W. Eosinophilia-myalgia syndrome associated with exposure to tryptophan from a single manufacturer. J. Am. Med. Assoc. 264:1990;213-217.
28. Smith M.J., Mazzola E.P., Farrel T.J. et al. 1,1′-ethyl-idenebis(L-tryptophan), structure determination of contaminant '97'-implicated in the eosinophilia-myalgia syndrome (EMS). Tetrahedron Lett. 32:1991;991-994.
29. Sundberg, R.J., 1970. The Chemistry of Indoles, Academic Press, New York.
30. Swygert L.A., Maes E.F., Sewell L.E., Miller L., Falk H., Kilbourne E.M. Eosinophilia-myalgia syndrome: results of national surveillance. J. Am. Med. Assoc. 264:1990;1698-1703.
31. Swygert L.A., Back E.E., Auerbach S.B., Sewell L.E., Falk H. Eosinophilia-myalgia syndrome: mortality data from the US national surveillance system. J. Rheumatol. 20:1993;1711-1717.
32. Toyo'oka T., Yamazaki T., Tanimoto T. et al. Characterization of contaminants in EMS-associated L-tryptophan samples by high performance liquid chromatography. Chem. Pharm. Bull. 39:1991;820-822.
33. Trucksess M.W. Separation and isolation of trace impurities in L-tryptophan by high performance liquid chromatography. J. Chromatogr. 630:1993;147-150.
34. Varga J., Jimenez S.A., Uitto J. L-tryptophan and the eosinophilia-myalgia syndrome: current understanding of the etiology and pathogenesis. J. Invest. Dermatol. 100:1993;97S-105.
35. Waugh R.J., Bowie J.H., Hayes R.N. Collision induced dissociations of deprotonated peptides: dipeptides containing phenylalanine, tyrosine, histidine, and tryptophan. Int. J. Mass Spectrom. Ion Proc. 107:1991;333-347.
36. Williamson B.L., Benson L.M., Tomlinson A.J., Mayeno A.N., Gleich G.J., Naylor S. On-line HPLC-tandem mass spectrometry analysis of contaminants of L-tryptophan associated with the onset of the eosinophilia-myalgia syndrome. Toxicol. Letts. 92:1997;139-148.
37. Williamson B.L., Tomlinson A.J., Gleich G.J., Naylor S. Contaminants in commercial preparations of melatonin. Mayo Clin. Proc. 72:1997;1094-1095.
38. Williamson B.L., Tomlinson A.J., Gleich G.J., Naylor S. Structural characterization of contaminants found in commercial preparations of melatonin: similarities to case-associated analogs of L-tryptophan associated with eosinophilia-myalgia syndrome (EMS). Chem. Research Toxicol. 11:1998;234-240.
39. Williamson, B.L., Tomlinson, A.J., Hurth, K.M., Gleich, G.J., Naylor, S., 1998b. Rapid HPLC screening method for contaminants found in implicated L-tryptophan associated with eosinophilia myalgia syndrome and adulterated rapeseed oil associated with toxic oil syndrome. Biomed. Chromatogr. In press.
40. Williamson, B.L., Tomlinson, A.J., Gleich, G.J., Naylor, S., 1998c. Structural characterization of Peak X: the reported contaminant in case-associated 5-hydroxy-L-tryptophan associated with eosinophilia myalgia syndrome. J. Rheumatol. In Press.