Synthesis of bifunctional saxitoxin analogues by biotinylation

Toxicon

Volumn 53, Issue 4, 2009, Pages 460-465

  Robillot, Cedric ^a,b   Kineavy, Daniel ^a   Burnell, James ^c   Llewellyn, Lyndon E ^a  

^a AUSTRALIAN INSTITUTE OF MARINE SCIENCE   (Australia)

^b Cleveland Biosensors Pty Ltd   (Australia)

^c JAMES COOK UNIVERSITY   (Australia)

Author keywords

Avidin; Biotin; Conjugation; Saxiphilin; Saxitoxin; Streptavidin

Indexed keywords

AVIDIN; BIOTIN; CARBAMOYL PHOSPHATE; FRESH WATER; SAXITOXIN; STREPTAVIDIN;

ARTICLE; BINDING AFFINITY; BIOTINYLATION; CONJUGATION; MEDICAL RESEARCH; METHODOLOGY; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; SEA FOOD; SYNTHESIS; WATER CONTAMINATION;

BIOTIN; BIOTINYLATION; MOLECULAR STRUCTURE; PROTEIN BINDING; SAXITOXIN;

EID: 60449085442     PISSN: 00410101     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxicon.2008.12.020     Document Type: Article

References (29)

1. Diamandis E.P., and Christopoulos T.K. The biotin-(strept)avidin system: principles and applications in biotechnology. Clin. Chem. 37 (1991) 625-636
2. Dill K., Montgomery D.D., Wang W., and Tsai J.C. Antigen detection using microelectrode array microchips. Anal. Chim. Acta 444 (2001) 69-78
3. Doucette G.J., Logan M.M., Ramsdell J.S., and Van Dolah F.M. Development and preliminary validation of a microtiter plate-based receptor binding assay for paralytic shellfish poisoning toxins. Toxicon 35 (1997) 625-636
4. Gitlin G., Khait I., Bayer E.A., Wilchek M., and Muszkat K.A. Studies on the biotin-binding sites of avidin and streptavidin. A chemically induced dynamic nuclear polarization investigation of the status of tyrosine residues. Biochem. J. 259 (1989) 493-498
5. Hendrickson W.A., Pahler A., Smith J.L., Satow Y., Merritt E.A., and Phizackerley R.P. Crystal structure of core streptavidin determined from multiwavelength anomalous diffraction of synchrotron radiation. Proc. Natl. Acad. Sci. U.S.A. 86 (1989) 2190-2194
6. Holmberg A., Blomstergren A., Nord O., Lukacs M., Lundeberg J., and Uhlén M. The biotin-streptavidin interaction can be reversibly broken using water at elevated temperatures. Electrophoresis 26 (2005) 501-510
7. Koehn F.E., Ghazarossian V.E., Schantz E.J., Schnoes H.K., and Strong F.M. Derivatives of saxitoxin. Bioorg. Chem. 10 (1981) 412-428
8. Kulagina N.V., Mikulski C.M., Gray S., Ma W., Doucette G.J., Ramsdell J.S., and Pancrazio J.J. Detection of marine toxins, brevetoxin-3 and saxitoxin, in seawater using neuronal networks. Environ. Sci. Technol 40 (2006) 578-583
9. Lawrence J.F., Niedzwiadek B., and Menard C. Quantitative determination of paralytic shellfish poisoning toxins in shellfish using prechromatographic oxidation and liquid chromatography with fluorescence detection: collaborative study. J. AOAC Int 88 (2005) 1714-1732
10. Lewis P., Fritsch I., Gawley R.E., Henry R., Kight A., Lay Jr. J.O., Liyanage R., and McLachlin J. Dynamics of saxitoxin binding to saxiphilin c-lobe reveals conformational change. Toxicon 51 (2008) 208-217
11. Llewellyn L.E. Haemolymph protein in xanthid crabs: its selective binding of saxitoxin and possible role in toxin bioaccumulation. Mar. Biol. 128 (1997) 599-606
12. Llewellyn L.E. Saxitoxin, a toxic marine natural product that targets a multitude of receptors. Nat. Prod. Rep 23 (2006) 200-222
13. Llewellyn L.E., and Doyle J. The effect of shellfish extracts and other matrices upon the microtitre plate saxiphilin assay for paralytic shellfish poisons. Toxicon 39 (2000) 217-224
14. Llewellyn L.E., and Moczydlowski E.G. Characterization of saxitoxin binding to saxiphilin, a relative of the transferrin family that displays pH-dependent ligand binding. Biochemistry 33 (1994) 12312-12322
15. Llewellyn L.E., Bell P.M., and Moczydlowski E.G. Phylogenetic survey of soluble saxitoxin-binding activity in pursuit of the function and molecular evolution of saxiphilin, a relative of transferrin. Proc. R. Soc. Lond. B Biol. Sci. 264 (1997) 891-902
16. Llewellyn L.E., Doyle J., and Negri A. A high-throughput, microtiter plate assay for paralytic shellfish poisons using the saxitoxin-specific receptor, saxiphilin. Anal. Biochem 261 (1998) 51-56
17. Llewellyn L., Negri A., and Quilliam M. High affinity for the rat brain sodium channel of newly discovered hydroxybenzoate saxitoxin analogues from the dinoflagellate Gymnodinium catenatum. Toxicon 43 (2004) 101-104
18. Lonnberg M., and Carlsson J. Quantitative detection in the attomole range for immunochromatographic tests by means of a flatbed scanner. Anal. Biochem 293 (2001) 224-231
19. Louzao M.C., Vieytes M.R., Cabado A.G., de Sousa J., and Botana L.M. A fluorimetric microplate assay for detection and quantitation of toxins causing paralytic shellfish poisoning. Chem. Res. Toxicol 16 (2003) 433-438
20. Manger R.L., Leja L.S., Lee S.Y., Hungerford J.M., Kirkpatrick M.A., Yasumoto T., and Wekell M.M. Detection of paralytic shellfish poison by rapid cell bioassay: antagonism of voltage-gated sodium channel active toxins in vitro. J. AOAC Int 86 (2003) 540-543
21. McFarren E.F. Report on collaborative studies of the bioassay for paralytic shellfish poison. J. AOAC Int 42 (1959) 263-271
22. + channels by guanidinium toxins. J. Gen. Physiol 84 (1984) 687-704
23. Negri A.P., and Jones G.J. Bioaccumulation of paralytic shellfish poisoning (PSP) toxins from the cyanobacterium Anabaena circinalis by the freshwater mussel Alathyria condola. Toxicon 33 (1995) 667-678
24. Oshima Y., Itakura H., Lee K.-C., Yasumoto T., Blackburn S., and Hallegraeff G. Toxin production by the dinoflagellate Gymnodinium catenatum. In: Smayda T.J., and Shimizu Y. (Eds). Toxic Phytoplankton in the Sea (1993), Elsevier, New York 907-912
25. Ritchie J.M., Rogart R.B., and Strichartz G.R. A new method for labelling saxitoxin and its binding to non-myelinated fibres of the rabbit vagus, lobster walking leg, and garfish olfactory nerves. J. Physiol 261 (1976) 477-494
26. Usleber E., Schneider E., Terplan G., and Laycock M.V. Two formats of enzyme immunoassay for the detection of saxitoxin and other paralytic shellfish poisoning toxins. Food Addit. Contam 12 (1995) 405-413
27. Usup G., Leaw C.P., Cheah M.Y., Ahmad A., and Ng B.K. Analysis of paralytic shellfish poisoning toxin congeners by a sodium channel receptor binding assay. Toxicon 44 (2004) 37-43
28. van Egmond H.P. Natural toxins: risks, regulations and the analytical situation in Europe. Anal. Bioanal. Chem. 378 (2004) 1152-1160
29. Yoo J.S., Cheun B.S., Park I.S., Song Y.C., Seo Y., Kim N.G., Shin H.W., and Lee J.H. Use of sodium transfer tissue biosensor (STTB) for monitoring of marine toxic organism. J. Environ. Biol. 25 (2004) 431-436