High-throughput receptor-based assay for the detection of spirolides by chemiluminescence

Toxicon

Volumn 75, Issue , 2013, Pages 35-43

  Rodríguez, Laura P ^a   Vilariño, Natalia ^a   Molgó, Jordi ^b   Aráoz, Rómulo ^b   Botana, Luis M ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b CNRS   (France)

Author keywords

bungarotoxin; Competition assay; Cyclic imines; Nicotinic acetylcholine receptors; Single laboratory pre validation

Indexed keywords

13 DESMETHYL SPIROLIDE C; 13,19 DIDESMEHTYL SPIROLIDE C; 20 METHYL SPIROLIDE G; ALPHA BUNGAROTOXIN; BIOTIN; HORSERADISH PEROXIDASE; IMMUNOGLOBULIN G ANTIBODY; MARINE TOXIN; NICOTINIC RECEPTOR; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ANIMAL TISSUE; ARTICLE; CHEMICAL STRUCTURE; CHEMOLUMINESCENCE; CONTROLLED STUDY; CROSS REACTION; HIGH THROUGHPUT SCREENING; IMMOBILIZATION; NONHUMAN; PRIORITY JOURNAL; RECEPTOR BINDING; SCALLOP; SENSITIVITY ANALYSIS; SHELLFISH; TOXICITY;

ARMORACIA RUSTICANA; DINOPHYCEAE;

BOVINE SERUM ALBUMIN; BSA; COEFFICIENT OF VARIATION; COMPETITION ASSAY; CR; CROSS-REACTIVITY; CV; CYCLIC IMINES; HORSERADISH PEROXIDASE; HRP; I.P.; INTRAPERITONEAL; LC-MS; LIMIT OF DETECTION; LIQUID CHROMATOGRAPHY-MASS SPECTROMETRY; LOD; MBA; MOLECULAR-WEIGHT-CUTOFF; MOUSE BIOASSAY; MWCO; NACHR; NICOTINIC ACETYLCHOLINE RECEPTOR; NICOTINIC ACETYLCHOLINE RECEPTORS; PBS; PHOSPHATE-BUFFERED SALINE; SD; SEM; SINGLE-LABORATORY PRE-VALIDATION; STANDARD DEVIATION; STANDARD ERROR OF THE MEAN; Α-BTX; Α-BUNGAROTOXIN;

ANIMALS; BIOLOGICAL ASSAY; BIOTIN; BUNGAROTOXINS; DINOFLAGELLIDA; FOOD CONTAMINATION; HIGH-THROUGHPUT SCREENING ASSAYS; LIMIT OF DETECTION; LUMINESCENCE; LUMINESCENT MEASUREMENTS; MARINE TOXINS; RECEPTORS, NICOTINIC; SHELLFISH; SPIRO COMPOUNDS; STREPTAVIDIN;

EID: 84885300999     PISSN: 00410101     EISSN: 18793150     Source Type: Journal    
DOI: 10.1016/j.toxicon.2013.06.015     Document Type: Article

References (38)

1. Aasen J., MacKinnon S.L., LeBlanc P., Walter J.A., Hovgaard P., Aune T., Quilliam M.A. Detection and identification of spirolides in Norwegian shellfish and plankton. Chem. Res. Toxicol. 2005, 18:509-515.
2. Álvarez G., Uribe E., Avalos P., Marino C., Blanco J. First identification of azaspiracid and spirolides in Mesodesma donacium and Mulinia edulis from Northern Chile. Toxicon 2009, 55:638-641.
3. Amzil Z., Sibat M., Royer F., Masson N., Abadie E. Report on the first detection of pectenotoxin-2, spirolide-A and their derivatives in French shellfish. Mar. Drugs 2007, 5:168-179.
4. Anderson D.M., Kulis D.M., Keafer B.A., Gribble K.E., Marin R., Scholin C.A. Identification and enumeration of Alexandrium spp. from the Gulf of Maine using molecular probes. Deep Sea Res. Part 2 Top Stud. Oceanogr. 2005, 52:2467-2490.
5. Aráoz R., Ramos S., Pelissier F., Guérineau V., Benoit E., Vilariño N., Botana L.M., Zakarian A., Molgó J. Coupling the Torpedo microplate-receptor binding assay with mass spectrometry to detect cyclic imine neurotoxins. Anal. Chem. 2012, 10445-10453.
6. Biré R., Krys S., Frémy J.M., Dragacci S., Stirling D., Kharrat R. First evidence on occurrence of gymnodimine in clams from Tunisia. J. Nat. Toxin. 2002, 11:269-275.
7. Bourne Y., Radic Z., Araoz R., Talley T.T., Benoit E., Servent D., Taylor P., Molgó J., Marchot P. Structural determinants in phycotoxins and AChBP conferring high affinity binding and nicotinic AChR antagonism. Proc. Natl. Acad. Sci. U. S. A. 2010, 107:6076-6081.
8. Cembella A.D., Lewis N.I., Quilliam M.A. Spirolide composition of micro-extracted pooled cells isolated from natural plankton assemblages and from cultures of the dinoflagellate Alexandrium ostenfeldii. Nat. Toxin. 1999, 7:197-206.
9. Cembella A.D., Lewis N.I., Quilliam M.A. The marine dinoflagellate Alexandrium ostenfeldii (Dinophyceae) as the causative organism of spirolide shellfish toxins. Phycologia 2000, 39:67.
10. Ciminiello P., Dell'Aversano C., Fattorusso E., Magno S., Tartaglione L., Cangini M., Pompei M., Guerrini F., Boni L., Pistocchi R. Toxin profile of Alexandrium ostenfeldii (Dinophyceae) from the Northern Adriatic Sea revealed by liquid chromatography-mass spectrometry. Toxicon 2006, 47:597-604.
11. EC 2002/657/EC: Commission Decision of 12 August 2002 implementing Council Directive 96/23/EC concerning the performance of analytical methods and the interpretation of results. Off. J. Eur. Communities 2002, L221:8.
12. Fonfría E.S., Vilariño N., Espiña B., Louzao M.C., Álvarez M., Molgó J., Araoz R., Botana L.M. Feasibility of gymnodimine and 13-desmethyl C spirolide detection by fluorescence polarization using a receptor-based assay in shellfish matrixes. Anal. Chim. Acta 2010, 657:75-82.
13. Fonfría E.S., Vilariño N., Molgó J., Araoz R., Otero P., Espiña B., Louzao M.C., Álvarez M., Botana L.M. Detection of 13,19-didesmethyl C spirolide by fluorescence polarization using Torpedo electrocyte membranes. Anal. Biochem. 2010, 403:102-107.
14. Fux E., McMillan D., Biré R., Hess P. Development of an ultra-performance liquid chromatography-mass spectrometry method for the detection of lipophilic marine toxins. J. Chromatogr. A 2007, 1157:273-280.
15. Hu T., Burton I.W., Cembella A.D., Curtis J.M., Quilliam M.A., Walter J.A., Wright J.L. Characterization of spirolides A, C, and 13-desmethyl C, new marine toxins isolated from toxic plankton and contaminated shellfish. J. Nat. Prod. 2001, 64:308-312.
16. Hu T., Curtis J.M., Oshima Y., Quilliam M.A., Walter J.A., Watson-Wright W.M., Wright J.L.C. Spirolides B and D, two novel macrocycles isolated from the digestive glands of shellfish. J. Chem. Soc. Chem. Commun. 1995, 20:2159-2161.
17. Hu T., Curtis J.M., Walter J.A., Wright J.L.C. Characterization of biologically inactive spirolides E and F: Identification of the spirolide pharmacophore. Tetrahedron Lett. 1996, 37:7671-7674.
18. John U., Cembella A., Hummert C., Elbrächter M., Groben R., Medlin L. Discrimination of the toxigenic dinoflagellates Alexandrium tamarense and A. ostenfeldii in co-occurring natural populations from Scottish coastal waters. Eur. J. Phycol. 2003, 38:25-40.
19. Kharrat R., Servent D., Girard E., Ouanounou G., Amar M., Marrouchi R., Benoit E., Molgó J. The marine phycotoxin gymnodimine targets muscular and neuronal nicotinic acetylcholine receptor subtypes with high affinity. J. Neurochem. 2008, 107:952-963.
20. Lu C.-K., Lee G.-H., Huang R., Chou H.-N. Spiro-prorocentrimine, a novel macrocyclic lactone from a benthic Prorocentrum sp. of Taiwan. Tetrahedron Lett. 2001, 42:1713-1716.
21. MacKinnon S.L., Walter J.A., Quilliam M.A., Cembella A.D., Leblanc P., Burton I.W., Hardstaff W.R., Lewis N.I. Spirolides isolated from Danish strains of the toxigenic dinoflagellate Alexandrium ostenfeldii. J. Nat. Prod. 2006, 69:983-987.
22. Munday R. Toxicology of cyclic imines: gymnodimine, spirolides, pinnatoxins, pteriatoxins, prorocentrolide, spiro-prorocentrimine and symbioimines. Seafood and Freshwater Toxins: Pharmacology, Physiology and Detection 2008, 581-594. CRC Press, Boca Raton, FL. second ed. L.M. Botana (Ed.).
23. Munday R., Quilliam M.A., LeBlanc P., Lewis N., Gallant P., Sperker S.A., Ewart H.S., MacKinnon S.L. Investigations into the toxicology of spirolides, a group of marine phycotoxins. Toxins 2012, 4:1-14.
24. Munday R., Towers N.R., Mackenzie L., Beuzenberg V., Holland P.T., Miles C.O. Acute toxicity of gymnodimine to mice. Toxicon 2004, 44:173-178.
25. Otero P., Alfonso A., Rodríguez P., Rubiolo J.A., Cifuentes J.M., Bermúdez R., Vieytes M.R., Botana L.M. Pharmacokinetic and toxicological data of spirolides after oral and intraperitoneal administration. Food Chem. Toxicol. 2012, 50:232-237.
26. Richard D., Arsenault E., Cembella A., Quilliam M.A. Investigations into the toxicology and pharmacology of spirolides a novel group of shellfish toxins. Harmful Algal Blooms 2000: Proceedings of the Ninth International Conference on Harmful Algal Blooms 2001, 383-390. Intergovernmental Oceanographic Commission of UNESCO, Paris. G.M. Hallegraeff, S.I. Blackburn, C.J. Bolch, R.J. Lewis (Eds.).
27. Rodríguez L.P., Vilariño N., Molgó J., Araoz R., Antelo A., Vieytes M.R., Botana L.M. Solid-phase receptor-based assay for the detection of cyclic imines by chemiluminescence, fluorescence, or colorimetry. Anal. Chem. 2011, 83:5857-5863.
28. Rodríguez L.P., Vilariño N., Molgó J., Aráoz R., Louzao M.C., Taylor P., Talley T.T., Botana L.M. Development of a solid-phase receptor-based assay for the detection of cyclic imines using a microsphere-flow cytometry system. Anal. Chem. 2013, 85:2340-2347.
29. Seki T., Satake M., Mackenzie L., Kaspar H.F., Yasumoto T. Gymnodimine, a new marine toxin of unprecedented structure isolated from New Zealand oysters and the dinoflagellate, Gymnodinium sp. Tetrahedron Lett. 1995, 36:7093-7096.
30. Sleno L., Volmer D.A. Toxin screening in phytoplankton: detection and quantitation using MALDI triple quadrupole mass spectrometry. Anal. Chem. 2005, 77:1509-1517.
31. Stirling D.J. Survey of historical New Zealand shellfish samples for accumulation of gymnodimine. N. Z. J. Mar. Freshw. Res. 2001, 35:851-857.
32. Takada N., Umemura N., Suenaga K., Chou T., Nagatsu A., Haino T., Yamada K., Uemura D. Pinnatoxins B and C, the most toxic components in the pinnatoxin series from the Okinawan bivalve Pinna muricata. Tetrahedron Lett. 2001, 42:3491-3494.
33. Takada N., Umemura N., Suenaga K., Uemura D. Structural determination of pteriatoxins A, B and C, extremely potent toxins from the bivalve Pteria penguin. Tetrahedron Lett. 2001, 42:3495-3497.
34. Torigoe K., Murata M., Yasumoto T. Prorocentrolide, a toxic nitrogenous macrocycle from a marine dinoflagellate, Prorocentrum lima. J. Am. Chem. Soc. 1988, 110:7876-7877.
35. Touzet N., Franco J.M., Raine R. Morphogenetic diversity and biotoxin composition of Alexandrium (Dinophyceae) in Irish coastal waters. Appl. Environ. Microbiol. 2008, 7:782-797.
36. Uemura D., Chou T., Haino T., Nagatsu A., Fukuzawa S., Zheng S.-Z., Chen H.-S. Pinnatoxin A: a toxic amphoteric macrocycle from the Okinawan bivalve Pinna muricata. J. Am. Chem. Soc. 1995, 117:1155-1156.
37. Vilariño N., Fonfría E.S., Molgó J., Araoz R., Botana L.M. Detection of gymnodimine-A and 13-desmethyl C spirolide phycotoxins by fluorescence polarization. Anal. Chem. 2009, 81:2708-2714.
38. Villar Gonzalez A., Rodriguez-Velasco M.L., Ben-Gigirey B., Botana L.M. First evidence of spirolides in Spanish shellfish. Toxicon 2006, 48:1068-1074.