Analysis of interactions of brevetoxin-B and human serum albumin by liquid chromatography/mass spectrometry

Chemical Research in Toxicology

Volumn 24, Issue 1, 2011, Pages 54-64

  Wang, Zhihong ^a   Ramsdell, John S ^a  

^a CENTER FOR COASTAL ENVIRONMENTAL HEALTH AND BIOMOLECULAR RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BREVETOXIN; HUMAN SERUM ALBUMIN;

ARTICLE; CHEMICAL STRUCTURE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PROTEIN ANALYSIS; PROTEIN PROTEIN INTERACTION;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CHYMOTRYPSIN; CYSTEINE; DINOFLAGELLIDA; HISTIDINE; HUMANS; MARINE TOXINS; MASS SPECTROMETRY; OXOCINS; PRONASE; PROTEIN BINDING; SERUM ALBUMIN; TRYPSIN;

ALGAE; DINOPHYCEAE; KARENIA BREVIS;

EID: 78651512227     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx1002854     Document Type: Article

References (45)

1. Landsberg, J. H., Flewelling, L. J., and Naar, J. (2009) Karenia brevis red tides, brevetoxins in the food web, and impacts on natural resources: decadal advancements Harmful Algae 8, 598-607
2. Shimizu, Y., Chou, H. N., and Bando, H. (1986) Structure of brevetoxin A (GB-1 toxin), the most potent toxin in the Florida red tide organism Gymnodinium breve (Ptychodiscus brevis) J. Am. Chem. Soc. 108, 514-515
3. Lin, Y.-Y., Risk, M., Ray, S. M., Van Engen, D., Clardy, J., Golik, J., James, J. C., and Nakanishi, K. (1981) Isolation and structure of brevetoxin B from the "red tide" dinoflagellate Ptychodiscus brevis (Gymnodinium breve) J. Am. Chem. Soc. 103, 6773-6775
4. Cheng, Y. S., Zhou, Y., Irvin, C. M., Pierce, R. H., Naar, J., Backer, L. C., Fleming, L. E., Kirkpatrick, B., and Baden, D. G. (2005) Characterization of marine aerosol for assessment of human exposure to brevetoxins Environ. Health Perspect. 113, 638-643
5. Pierce, R. H., Henry, M. S., Blum, P. C., Hamel, S. L., Kirkpatrick, B., Cheng, Y. S., Zhou, Y., Irvin, C. M., Naar, J., Weidner, A., Fleming, L. E., Backer, L. C., and Baden, D. G. (2005) Brevetoxins composition in water and marine aerosol along a Florida beach: assessing potential human exposure to marine biotoxins Harmful Algae 4, 965-972
6. Wang, Z., Plakas, S. M., El Said, K. R., Jester, E. L. E., Granade, H. R., and Dickey, R. W. (2004) LC/MS analysis of brevetoxin metabolites in the Eastern oyster (Crassostrea virginica) Toxicon 43, 455-465
7. Plakas, S. M., Wang, Z., El Said, K. R., Jester, E. L. E., Granade, H. R., and Dickey, R. W. (2004) Brevetoxin metabolism and elimination in the Eastern oyster (Crassostrea virginica) after control exposure to Karenia brevis Toxicon 44, 677-685
8. Radwan, F. F. Y., Wang, Z., and Ramsdell, J. S. (2005) Identification of a rapid detoxification mechanism for brevetoxin in rats Toxicol. Sci. 85, 839-846
9. Ramsdell, J. S. (2008) The molecular and integrative basis to brevetoxin toxicity. In Seafood and Freshwater Toxins; Pharmacology, Physiology and Detection (Botana, L., Ed.), pp 519 -550, Taylor and Francis, London, U.K.
10. Bossart, G. D., Baden, D. G., Ewing, R. Y., Roberts, B., and Wright, S. D. (1998) Brevetoxicosis in manatees (Trichechus manatus latirostris) from the 1996 epizootic: gross, histologic, and immunohistochemical features Toxicol. Pathol. 26, 276-282
11. Walsh, K. J., Leggett, S. R., Carter, B. J., and Colle, C. (2010) Effects of brevetoxin exposure on the immune system of loggerhead sea turtles Aquat. Toxicol. 97, 293-303
12. Woofter, R., Dechraoui, M. Y., Garthwaite, I., Towers, N. R., Gordon, C. J., Cordova, J., and Ramsdell, J. S. (2003) Measurement of brevetoxin levels by radioimmunoassay of blood collection cards after acute, long-term, and low-dose exposure in mice Environ. Health Perspect. 111, 1595-1600
13. Woofter, R., Brendtro, K., and Ramsdell, J. S. (2005) Uptake and elimination of brevetoxin in blood of striped mullet (Mugil cephalus) after aqueous exposure to Karenia brevis Environ. Health Perspect. 113, 11-16
14. Woofter, R., Spiess, P. C., and Ramsdell, J. S. (2005) Distribution of brevetoxin (PbTx-3) in mouse plasma: association with high-density lipoproteins Environ. Health Perspect. 113, 1491-1496
15. Woofter, R. and Ramsdell, J. S. (2007) Distribution of brevetoxin to lipoproteins in human plasma Toxicon 49, 1010-1018
16. Uchida, K. and Stadtman, E. R. (1992) Modification of histidine residues in proteins by reaction with 4-hydroxynonenal Proc. Natl. Acad. Sci. U.S.A. 89, 4544-4548
17. Szweda, L. I., Uchida, K., Tsai, L., and Stadtman, E. R. (1993) Inactivation of glucose-6-phosphate dehyddrogenase by 4-hydroxy-2-nonenal J. Biol. Chem. 268, 3342-3347
18. Bolgar, M. S. and Gaskell, S. J. (1996) Determination of the sites of 4-hydroxy-2-nonenal adduction to protein by electrospray tandem mass spectrometry Anal. Chem. 68, 2325-2330
19. Cohn, J. A., Tsai, L., Friguet, B., and Szweda, L. I. (1996) Chemical characterization of a protein-4-hydroxy-2-nonenal cross-link: immunochemical detection in mitochondria exposed to oxidative stress Arch. Biochem. Biophys. 328, 158-164
20. Requena, J. R., Fu, M. X., Ahmed, M. U., Jenkins, A. J., Lyons, T. J., Baynes, J. W., and Thorpe, S. R. (1997) Quantification of malondialdehyde and 4-hydroxynonenal adducts to lysine residues in native and oxidized human low-density lipoprotein Biochem. J. 322, 317-325
21. Crabb, J. W., O'Neil, J., Miyagi, M., West, K., and Hoff, H. F. (2002) Hydroxynonenal inactivates cathepsin B by forming Michael adducts with active site residues Protein Sci. 11, 831-840
22. Aldini, G., Dalle-Donne, I., Vistoli, G., Facino, R. M., and Carini, M. (2005) Covalent modification of actin by 4-hydroxy-trans -2-nonenal (HNE): LC-ESI-MS/MS evidence for Cys374 Michael adduction J. Mass Spectrom. 40, 946-954
23. Szapacs, M. E., Riggins, J. N., Zimmerman, L. J., and Liebler, D. C. (2006) Covalent adduction of human serum albumin by 4-hydroxy-trans -2-nonenal: kinetic analysis of competing alkylation reactions Biochemistry 45, 10521-10528
24. Dalle-Donne, I., Carini, M., Vistoli, G., Gamberoni, L., Giustarini, D., Colombo, R., Facino, R. M., Rossi, R., Milzani, A., and Aldini, G. (2007) Actin Cys374 as a nucleophilic target of α,β-unsaturated aldehydes Free Radical Biol. Med 42, 583-598
25. Aldini, G., Vistoli, G., Regazzoni, L., Gamberoni, L., Facino, R. M., Yamaguchi, S., Uchida, K., and Carini, M. (2008) Albumin is the main nucleophilic target of human plasma: a protective role against pro-atherogenic electrophilic reactive carbonyl species? Chem. Res. Toxicol. 21, 824-835
26. Selwood, A. I., van Ginkel, R., Wilkins, A. L., Munday, R., Ramsdell, J. S., Jensen, D. J., Cooney, J. M., and Miles, C. O. (2008) Semisynthesis of S-desoxybrevetoxin-B2 and brevetoxin-B2, and assessment of their acute toxicities Chem. Res. Toxicol. 21, 944-950
27. Roth, P. B., Twiner, M. J., Wang, Z., Bottein Dechraoui, M. Y., and Doucette, G. J. (2007) Fate and distribution of brevetoxin (PbTx) following lysis of Karenia brevis by algicidal bacterial, including analysis of open A-ring derivatives Toxicon 50, 1175-1191
28. Kinter, M. and Sherman, N. E. (2000) The preparation of protein digests for mass spectrometric sequencing experiments. In Protein Sequencing and Identification Using Tandem Mass Spectrometry (Kinter, M. and Sherman, N. E., Eds.), pp 161 -163, Wiley, New York.
29. Starkenmann, C. (2003) Analysis of a model reaction system containing cysteine and (E)-2-methyl-2-butenal, (E)-2-hexenal, or mesityl oxide J. Agric. Food Chem. 51, 7146-7155
30. Harris, R., Patel, S. U., and Viles, J. H. (1996) Observation of albumin resonance in proton nuclear magnetic resonance spectra of human blood plasma: N-terminal assignments aided by use of modified recombinant albumin Analyst 121, 913-922
31. Fasano, M., Curry, S., Terreno, E., Galliano, M., Fanali, G., Narciso, P., Notari, S., and Ascenzi, P. (2005) The extraordinary ligand binding properties of human serum albumin IUBMB Life 57, 787-796 (Pubitemid 43062399)
32. Skipper, P. L. (1996) Influence of tertiary structure on nucleophilic substitution reactions of proteins Chem. Res. Toxicol. 9, 918-923
33. Brunmark, P., Harriman, S., Skipper, P. L., Wishnok, J. S., Amin, S., and Tannenbaum, S. R. (1997) Identification of subdomain IB in human serum albumin as a major binding site for polycyclic aromatic hydrocarbon epoxides Chem. Res. Toxicol. 10, 880-886
34. Noort, D., Hulst, A. G., de Jong, L. P. A., and Benschop, H. P. (1999) Alkylation of human serum albumin by sulfur mustard in vitro and in vivo: mass spectrometric analysis of a cysteine adduct as a sensitive biomarker of exposure Chem. Res. Toxicol. 12, 715-721
35. Damsten, M. C., Commandeur, J. N. M., Fidder, A., Hulst, A. G., Touw, D., Noort, D., and Vermeulen, N. P. E. (2007) Liquid chromatography/tandem mass spectrometry detection of covalent binding of acetaminophen to human serum albumin Drug Metab. Dispos. 35, 1408-1417
36. Silveira, V. C., Caramori, G. F., Abbott, M. P., Goncalves, M. B., Petrilli, H. M., and Ferreira, A. M. D. C. (2009) Oxindole-schiff base copper(II) complexes interactions with human serum albumin: spectroscopic, oxidative damage, and computational studies J. Inorg. Biochem. 103, 1331-1341
37. Törnqvist, M., Fred, C., Haglund, J., Haglund, J., Helleberg, H., Paulsson, B., and Rydberg, P. (2002) Protein adducts: quantitative and qualitative aspects of their formation, analysis and applications J. Chromatogr., B 778, 279-308
38. Plakas, S. M. and Dickey, R. W. (2010) Advances in monitoring and toxicity assessment of brevetoxins in molluscan shellfish Toxicon 56, 137-149
39. Hinton, M. and Ramsdell, J. S. (2008) Brevetoxin in two planktivorous fishes after exposure to Karenia brevis: implications for food-web transfer to bottlenose dolphins Mar. Ecol. Prog. Ser. 356, 251-258
40. Flewelling, L. J., Naar, J. P., Abbott, J. P., Baden, D. G., Barros, N. B., Bossart, G. D., Bottein, M. Y., Hammond, D. G., Haubold, E. M., Heil, C. A., Henry, M. S., Jacocks, H. M., Leighfield, T. A., Pierce, R. H., Pitchford, T. D., Rommel, S. A., Scott, P. S., Steidinger, K. A., Truby, E. W., Van Dolah, F. M., and Landsberg, J. H. (2005) Brevetoxicosis: red tides and marine mammal mortalities Nature 435, 755-756
41. Walsh, C. J., Leggett, S. R., Henry, M. S., Blum, P. C., Osborn, S., and Pierce, R. H. (2009) Cellular metabolism of brevetoxin (PbTx-2) by a monocyte cell line (U-937) Toxicon 53, 135-145
42. Pournamdari, M., Saadi, A., Ellis, E., Andrew, R., Walker, B., and Watson, D. G. (2009) Development of a derivatisation method for the analysis of aldehyde modified amino acid residues in proteins by Fourier transform mass spectrometry Anal. Chim. Acta 633, 216-222
43. Friguet, B., Stadtman, E. R., and Szweda, L. I. (1994) Modification of glucose-6-phosphate dehydrogenase by 4-hydroxy-2-nonenal J. Biol. Chem. 269, 21639-21643
44. Fenaille, F., Guy, P. A., and Tabet, J. (2003) Study of protein modification by 4-hydroxy-2-nonenal and other short chain aldehydes analyzed by electrospray ionization tandem mass spectrometry J. Am. Soc. Mass Spectrom. 14, 215-226
45. Dechraoui, M. Y., Wang, Z., and Ramsdell, J. S. (2007) Intrinsic potency of synthetically prepared brevetoxin cysteine metabolites BTX-B2 and desoxyBTX-B2 Toxicon 50, 825-834