Production of monoclonal antibodies for sandwich immunoassay detection of Pacific ciguatoxins

Toxicon

Volumn 56, Issue 5, 2010, Pages 797-803

  Tsumuraya, Takeshi ^a   Fujii, Ikuo ^a   Hirama, Masahiro ^b  

^a Osaka Prefecture University   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

Ciguatera; Ciguatoxin; Monoclonal antibody; Sandwich ELISA

Indexed keywords

51 HYDROXY CTX3C; BREVETOXIN; BREVETOXIN A; BREVETOXIN B; CIGUATOXIN; CTX3C; HAPTEN; MAITOTOXIN; MONOCLONAL ANTIBODY; OKADAIC ACID; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIBODY PRODUCTION; ARTICLE; BINDING AFFINITY; CONJUGATION; CONTROLLED STUDY; CROSS REACTION; ENZYME IMMUNOASSAY; ENZYME LINKED IMMUNOSORBENT ASSAY; HAPTEN CARRIER COMPLEX; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN SYNTHESIS; TOXIN ANALYSIS; TOXIN STRUCTURE;

ANIMALS; ANTIBODIES, MONOCLONAL; CIGUATOXINS; ENZYME-LINKED IMMUNOSORBENT ASSAY; HAPTENS; MICE;

CIGUATERA; MUS;

EID: 77954231219     PISSN: 00410101     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxicon.2009.06.003     Document Type: Article

References (36)

1. Arevalo J.H., Taussig M.J., Wilson I.A. Molecular basis of crossreactivity and the limits of antibody-antigen complementarity. Nature 1993, 365:859.
2. Dechraoui M.-Y., Naar J., Pauillac S., Legrand A.-M. Ciguatoxins and brevetoxins, neurotoxic polyether compounds active on sodium channels. Toxicon 1999, 37:125.
3. Friguet B., Chaffotte A.F., Djabadi-Ohaniance L., Goldberg M.E. Measurements of the true affinity constant in solution of antigen-antibody complexes by enzyme-linked immunosorbent assay. J. Immunol. Methods 1985, 77:305.
4. Hirama M., Oishi T., Uehara H., Inoue M., Maruyama M., Oguri H., Satake M. Total synthesis of ciguatoxin CTX3C. Science 2001, 294:1904.
5. Hokama Y., Banner A.H., Boylan D.B. A radioimmunoassay for the detection of ciguatoxin. Toxicon 1977, 15:317.
6. Hokama Y., Hong T.W.P., Isobe M., Ichikawa Y., Yasumoto T. Cross-reactivity of highly purified okadaic acid (OA), synthetic, spiroketal east sphere of OA and ciguatoxin. J. Clin. Lab. Anal. 1992, 6:54.
7. Hokama Y. Immunological studies using monoclonal antibodies for detection of low Dalton marine toxins. Food Addit. Contam. 1993, 10:83.
8. Hokama Y., Takenaka W.E., Nishimura K.L., Ebesu J.S.M.A. Simple membrane immunobead assay for detecting ciguatoxin and related polyethers from human ciguatera intoxication and natural reef fishes. J. AOAC Int. 1998, 81:727.
9. Inoue M., Miyazaki K., Uehara H., Maruyama M., Hirama M. First- and second-generation total synthesis of ciguatoxin CTX3C. Proc. Natl. Acad. Sci. U.S.A. 2004, 191:120.
10. Jeffrey P.D., Schildbach J.F., Chang C.-Y.Y., Kussie P.H., Margolies M.N., Sheriff S. Structure and specificity of the anti-digoxin antibody 40-50. J. Mol. Biol. 1995, 248:344.
11. Kurihara S., Tsumuraya T., Suzuki K., Kuroda M., Liu L., Takaoka Y., Fujii I. Antibody-catalyzed removal of the p-nitrobenzyl ester protecting group: the molecular basis of the broad substrate specificity. Chem. Eur. J. 2000, 6:1656.
12. Lewis R.J., Jones A. Characterization of ciguatoxins and ciguatoxin congeners present in ciguateric fish by gradient reverse-phase high performance liquid chromatography/mass spectroscopy. Toxicon 1997, 35:159.
13. Lewis R.J., Vernoux J.-P., Brereton I.M. Structure of Caribbean ciguatoxin isolated from Caranx latus. J. Am. Chem. Soc. 1998, 120:5914-5920.
14. Lewis R.J., Jones A., Vermoux J.-P. HPLC/tandem electrospray mass spectroscopy for the determination of sub-ppb levels of Pacific and Caribbean ciguatoxins in crude extracts of fish. Anal. Chem. 1999, 72:247.
15. Lewis R.J. The changing face of ciguatera. Toxicon 2001, 39:97.
16. Manger R.L., Leja L.S., Lee S.Y., Hungerford J.M., Hokama Y., Dickey R.W., Granade H.R., Lewis R., Yasumoto T., Wekell M.M. Detection of sodium channel toxins: directed cytotoxicity assays of purified ciguatoxins, brevetoxins, saxitoxins, and seafood extracts. J. AOAC Int. 1995, 78:521.
17. Murata M., Legrand A.-M., Ishibashi Y., Fukui M., Yasumoto T. Structures and configurations of ciguatoxin from the moray eel Gymnothorax javanicus and its likely precursor from the dinoflagellate Gambierdiscus toxicus. J. Am. Chem. Soc. 1990, 112:4380.
18. Nagumo Y., Oguri H., Shindo Y., Sasaki S., Oishi T., Hirama M., Tomioka Y., Mizugaki M., Tsumuraya T. Concise synthesis of ciguatoxin ABC-ring fragments and surface plasmon resonance study of the interaction of their BSA conjugates with monoclonal antibodies. Bioorg. Med. Chem. Lett. 2001, 15:2037.
19. Oguri H., Tanaka S., Hishiyama S., Oishi T., Hirama M., Tsumuraya T., Tomioka Y., Mizugaki M. Designed hapten aimed at anti-ciguatoxin monoclonal antibody: synthesis, immunization and discrimination of the C2 configuration. Synthesis 1999, 1431. (special issue).
20. Oguri H., Hirama M., Tsumuraya T., Fujii I., Maruyama M., Uehara H., Nagumo Y. Synthesis-based approach toward direct sandwich immunoassay for ciguatoxin CTX3C. J. Am. Chem. Soc. 2003, 125:7608.
21. Pauillac S., Sasaki M., Inoue M., Naar J., Branaa P., Chinain M., Tachibana K., Legrand A.-M. Characterization of mice antisera elicited with a ciguatoxin tetracyclic synthetic ring fragment (JKLM) conjugated to carrier proteins. Toxicon 2000, 38:669.
22. Poli M.A., Rewis R.J., Dickey R.W., Musser A.M., Buckner C.A., Carpenter L.G. Identification of Caribbean ciguatoxins as the cause of an outbreak of fish poisoning among US soldiers in Haiti. Toxicon 1997, 38:733.
23. Romesberg F.E., Spiller B., Schultz P.G., Raymond C.S. Immunological origins of binding and catalysis in a Diels-Alderase antibody. Science 1998, 279:1929.
24. Satake M., Murata M., Yasumoto T. The structure of CTX3C, a ciguatoxin congener isolated from cultured Gambierdiscus toxicus. Tetrahedron Lett. 1993, 34:1975.
25. Satake M., Fukui M., Legrand A.-M., Cruchet P., Yasumoto T. Isolation and structures of new ciguatoxin analogs, 2,3-dihydroxyCTX3C and 51-hydroxyCTX3C, accumulated in tropical reef fish. Tetrahedron Lett. 1998, 39:1197.
26. Scheuer P.J. Ciguatera and its off-shoots chance encounters en route to a molecular structure. Tetrahedron 1994, 50:3.
27. Suga H., Ersoy O., Tsumuraya T., Lee J., Sinskey A.J., Masamaune S. Esterolytic antibodies induced to haptens with a 1,2-amino alcohol functionality. J. Am. Chem. Soc. 1994, 116:487.
28. Tsumuraya T., Suga H., Meguro S., Tsunakawa A., Masamune S. Catalytic antibodies generated via homologous and heterologous immunization. J. Am. Chem. Soc. 1995, 117:11390.
29. Tsumuraya T., Takazawa N., Tsunakawa A., Fleck R., Masamune S. Catalytic antibodies induced by a zwitterionic hapten. Chem. Eur. J. 2001, 7:3748.
30. Tsumuraya T., Fujii I., Inoue M., Tatami A., Miyazaki K., Hirama M. Production of monoclonal antibodies for sandwich immunoassay detection of ciguatoxin 51-hydroxyCTX3C. Toxicon 2006, 48:287.
31. Tanaka F., Kinoshita K., Tanimura R., Fujii I. Relaxing substrate specificity in antibody-catalyzed reactions: enantioselective hydrolysis of N-Cbz-amino acid esters. J. Am. Chem. Soc. 1996, 118:2332.
32. Xu J., Deng Q., Chen J., Houk K.N., Bartek J., Hilvert D., Wilson I.A. Evolution of shape complementarity and catalytic efficiency from a primordial antibody template. Science 1999, 286:2345.
33. Yasumoto T., Fukui M., Sasaki K., Sugiyama K. Determination of marine toxins in foods. J. AOAC Int. 1995, 78:574.
34. Yasumoto T., Murata M. Marine toxins. Chem. Rev. 1993, 93:1897.
35. Yasumoto T., Igarashi T., Legrand A.-M., Cruchet P., Chinain M., Fujita T., Naokki H. Structural elucidation of ciguatoxin congeners by fast-atom bombardment tandem mass spectroscopy. J. Am. Chem. Soc. 2000, 122:4988.
36. Yasumoto T. The chemistry and biological function of natural marine toxins. Chem. Rec. 2001, 1:228.