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Journal articles on the topic 'Azaspiracidi'

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Author: Grafiati
Published: 1 April 2023

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1

Hamilton, Brett, Mónica Díaz Sierra, Mary Lehane, Ambrose Furey, and Kevin J. James. "The fragmentation pathways of azaspiracids elucidated using positive nanospray hybrid quadrupole time-of-flight (QqTOF) mass spectrometry." Spectroscopy 18, no. 2 (2004): 355–62. http://dx.doi.org/10.1155/2004/949018.

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The azaspiracids, AZA1, AZA2 and AZA3, are the predominant shellfish toxins responsible for the human toxic syndrome, azaspiracid poisoning. Collision induced dissociation (CID) mass spectra were generated for azaspiracids using nano-electrospray ionisation (ESI) with a hybrid quadrupole time-of-flight (QqTOF) mass spectrometer in positive mode. Six main backbone fragmentations of the polyether skeleton of azaspiracids were observed as well as multiple neutral losses of water molecules from the parent and product ions. The characteristic charge-remote fragmentation of the carbon skeleton of azaspiracids produced nitrogenous ions. The three azaspiracids differ from one another by 14 Da due to methylation in the A- and E-rings. Three fragmentation pathways, involving cleavage of the E-ring, C27–C28 and G-ring, gave ions that were common to all azaspiracids. Another three fragmentations involving the A-ring, C-ring and C19–C20, were useful for distinguishing between azaspiracid analogues. Multiple tandem ion‒trap mass spectrometry (MSn) was used to confirm the fragmentation pathways.
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2

Kilcoyne, Jane, Adela Keogh, Ger Clancy, Patricia LeBlanc, Ian Burton, Michael A. Quilliam, Philipp Hess, and Christopher O. Miles. "Improved Isolation Procedure for Azaspiracids from Shellfish, Structural Elucidation of Azaspiracid-6, and Stability Studies." Journal of Agricultural and Food Chemistry 60, no. 10 (March 2, 2012): 2447–55. http://dx.doi.org/10.1021/jf2048788.

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3

Abal, Paula, M. Carmen Louzao, María Fraga, Natalia Vilariño, Sara Ferreiro, Mercedes R. Vieytes, and Luis M. Botana. "Absorption and Effect of Azaspiracid-1 Over the Human Intestinal Barrier." Cellular Physiology and Biochemistry 43, no. 1 (2017): 136–46. http://dx.doi.org/10.1159/000480331.

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Background: Azaspiracids (AZAs) are marine biotoxins produced by the dinoflagellates genera Azadinium and Amphidoma. These toxins cause azaspiracid poisoning (AZP), characterized by severe gastrointestinal illness in humans after the consumption of bivalve molluscs contaminated with AZAs. The main aim of the present study was to examine the consequences of human exposure to AZA1 by the study of absorption and effects of the toxin on Caco-2 cells, a reliable model of the human intestine. Methods: The ability of AZA1 to cross the human intestinal epithelium has been evaluated by the Caco-2 transepithelial permeability assay. The toxin has been detected and quantified using a microsphere-based immunoassay. Cell alterations and ultrastructural effects has been observed with confocal and transmission electron microscopy Results: AZA1 was absorbed by Caco-2 cells in a dose-dependent way without affecting cell viability. However, modifications on occludin distribution detected by confocal microscopy imaging indicated a possible monolayer integrity disruption. Nevertheless, transmission electron microscopy imaging revealed ultrastructural damages at the nucleus and mitochondria with autophagosomes in the cytoplasm, however, tight junctions and microvilli remained unaffected. Conclusion: After the ingestion of molluscs with the AZA1, the toxin will be transported through the human intestinal barrier to blood causing damage on epithelial cells.
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4

Trainer, Vera L., and Teri L. King. "SoundToxins: A Research and Monitoring Partnership for Harmful Phytoplankton in Washington State." Toxins 15, no. 3 (March 2, 2023): 189. http://dx.doi.org/10.3390/toxins15030189.

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The more frequent occurrence of marine harmful algal blooms (HABs) and recent problems with newly-described toxins in Puget Sound have increased the risk for illness and have negatively impacted sustainable access to shellfish in Washington State. Marine toxins that affect safe shellfish harvest because of their impact on human health are the saxitoxins that cause paralytic shellfish poisoning (PSP), domoic acid that causes amnesic shellfish poisoning (ASP), diarrhetic shellfish toxins that cause diarrhetic shellfish poisoning (DSP) and the recent measurement of azaspiracids, known to cause azaspiracid poisoning (AZP), at low concentrations in Puget Sound shellfish. The flagellate, Heterosigma akashiwo, impacts the health and harvestability of aquacultured and wild salmon in Puget Sound. The more recently described flagellates that cause the illness or death of cultivated and wild shellfish, include Protoceratium reticulatum, known to produce yessotoxins, Akashiwo sanguinea and Phaeocystis globosa. This increased incidence of HABs, especially dinoflagellate HABs that are expected in increase with enhanced stratification linked to climate change, has necessitated the partnership of state regulatory programs with SoundToxins, the research, monitoring and early warning program for HABs in Puget Sound, that allows shellfish growers, Native tribes, environmental learning centers and citizens, to be the “eyes on the coast”. This partnership enables safe harvest of wholesome seafood for consumption in the region and helps to describe unusual events that impact the health of oceans, wildlife and humans.
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5

Kilcoyne, Jane, Pearse McCarron, Michael J. Twiner, Ciara Nulty, Sheila Crain, Michael A. Quilliam, Frode Rise, Alistair L. Wilkins, and Christopher O. Miles. "Epimers of Azaspiracids: Isolation, Structural Elucidation, Relative LC-MS Response, andin VitroToxicity of 37-epi-Azaspiracid-1." Chemical Research in Toxicology 27, no. 4 (February 7, 2014): 587–600. http://dx.doi.org/10.1021/tx400434b.

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6

Krock, Bernd, Urban Tillmann, Uwe John, and Allan D. Cembella. "Characterization of azaspiracids in plankton size-fractions and isolation of an azaspiracid-producing dinoflagellate from the North Sea." Harmful Algae 8, no. 2 (January 2009): 254–63. http://dx.doi.org/10.1016/j.hal.2008.06.003.

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7

OFUJI, Katsuya, Masayuki SATAKE, Terry MCMAHON, Kevin J. JAMES, Hideo NAOKI, Yasukatsu OSHIMA, and Takeshi YASUMOTO. "Structures of Azaspiracid Analogs, Azaspiracid-4 and Azaspiracid-5, Causative Toxins of Azaspiracid Poisoning in Europe." Bioscience, Biotechnology, and Biochemistry 65, no. 3 (January 2001): 740–42. http://dx.doi.org/10.1271/bbb.65.740.

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8

Rossi, Rachele, Carmela Dell’Aversano, Bernd Krock, Patrizia Ciminiello, Isabella Percopo, Urban Tillmann, Vittorio Soprano, and Adriana Zingone. "Mediterranean Azadinium dexteroporum (Dinophyceae) produces six novel azaspiracids and azaspiracid-35: a structural study by a multi-platform mass spectrometry approach." Analytical and Bioanalytical Chemistry 409, no. 4 (November 7, 2016): 1121–34. http://dx.doi.org/10.1007/s00216-016-0037-4.

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9

Li, Jialiang, Xiaohua Li, and David R. Mootoo. "Synthetic and Computational Studies on the ABC Trioxadispiroketal Subunit of the Marine Biotoxin Azaspiracid-1." Natural Product Communications 3, no. 11 (November 2008): 1934578X0800301. http://dx.doi.org/10.1177/1934578x0800301106.

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The trioxadispiroketal residue in the marine biotoxin azaspiracid-1, which exists in a configuration capable of exhibiting a double anomeric effect, is believed to be the thermodynamically most stable bis-spiroketal diastereomer. In order to get insight into how structural factors affect this equilibrium, a simplified ABC trioxadispiroketal analog of azaspiracid-1 was synthesized and subjected to equilbration and computational studies. Compound 7, which represents a double anomeric effect was obtained as the major isomer, together with diastereomers 14 and 15, in a respective ratio of 62:22:16. DFT calculations for 7, 14 and 15 qualitatively matched this observation. These results suggest that while a double anomeric effect may play a major role in the stability of the trioxadispiroketal configuration in the more complex natural product, the substitution pattern of the C ring is also a contributing factor.
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10

Alfonso, Carmen, Amparo Alfonso, Paz Otero, Paula Rodríguez, Mercedes R. Vieytes, Chris Elliot, Cowan Higgins, and Luis M. Botana. "Purification of five azaspiracids from mussel samples contaminated with DSP toxins and azaspiracids." Journal of Chromatography B 865, no. 1-2 (April 2008): 133–40. http://dx.doi.org/10.1016/j.jchromb.2008.02.020.

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11

Krock, Bernd, Urban Tillmann, Daniela Voß, Boris P. Koch, Rafael Salas, Matthias Witt, Éric Potvin, and Hae Jin Jeong. "New azaspiracids in Amphidomataceae (Dinophyceae)." Toxicon 60, no. 5 (October 2012): 830–39. http://dx.doi.org/10.1016/j.toxicon.2012.05.007.

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12

Brombacher, Stephan, Suzanne Edmonds, and Dietrich A. Volmer. "Studies on azaspiracid biotoxins. II. Mass spectral behavior and structural elucidation of azaspiracid analogs." Rapid Communications in Mass Spectrometry 16, no. 24 (2002): 2306–16. http://dx.doi.org/10.1002/rcm.863.

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13

Nicolaou, K. C., Michael O. Frederick, Goran Petrovic, Kevin P. Cole, and Eriketi Z. Loizidou. "Total Synthesis and Confirmation of the Revised Structures of Azaspiracid-2 and Azaspiracid-3." Angewandte Chemie 118, no. 16 (April 10, 2006): 2671–77. http://dx.doi.org/10.1002/ange.200600295.

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14

Nicolaou, K. C., Michael O. Frederick, Goran Petrovic, Kevin P. Cole, and Eriketi Z. Loizidou. "Total Synthesis and Confirmation of the Revised Structures of Azaspiracid-2 and Azaspiracid-3." Angewandte Chemie International Edition 45, no. 16 (April 10, 2006): 2609–15. http://dx.doi.org/10.1002/anie.200600295.

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15

Nicolaou, K. C., and Jason S. Chen. "Total synthesis of complex heterocyclic natural products." Pure and Applied Chemistry 80, no. 4 (January 1, 2008): 727–42. http://dx.doi.org/10.1351/pac200880040727.

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Total synthesis campaigns toward complex heterocyclic natural products are a prime source of inspiration for the design and execution of complex cascade sequences, powerful reactions, and efficient synthetic strategies. We highlight selected examples of such innovations in the course of our total syntheses of diazonamide A, azaspiracid-1, thiostrepton, 2,2'-epi-cytoskyrin A and rugulosin, abyssomycin C, platensimycin, and uncialamycin.
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16

Vilariño, Natalia. "Marine toxins and the cytoskeleton: azaspiracids." FEBS Journal 275, no. 24 (October 29, 2008): 6075–81. http://dx.doi.org/10.1111/j.1742-4658.2008.06713.x.

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17

Krock, Bernd, Urban Tillmann, Jan Tebben, Nicole Trefault, and Haifeng Gu. "Two novel azaspiracids from Azadinium poporum, and a comprehensive compilation of azaspiracids produced by Amphidomataceae, (Dinophyceae)." Harmful Algae 82 (February 2019): 1–8. http://dx.doi.org/10.1016/j.hal.2018.12.005.

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18

Geisler, Lisa K., Son Nguyen, and Craig J. Forsyth. "Synthesis of the Azaspiracid-1 Trioxadispiroketal." Organic Letters 6, no. 23 (November 2004): 4159–62. http://dx.doi.org/10.1021/ol048581a.

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19

Frederick, Michael O., Sandra De Lamo Marin, Kim D. Janda, K. C. Nicolaou, and Tobin J. Dickerson. "Monoclonal Antibodies with Orthogonal Azaspiracid Epitopes." ChemBioChem 10, no. 10 (July 6, 2009): 1625–29. http://dx.doi.org/10.1002/cbic.200900201.

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20

Tillmann, Urban, C. Marcela Borel, Facundo Barrera, Rubén Lara, Bernd Krock, Gastón O. Almandoz, Matthias Witt, and Nicole Trefault. "Azadinium poporum from the Argentine Continental Shelf, Southwestern Atlantic, produces azaspiracid-2 and azaspiracid-2 phosphate." Harmful Algae 51 (January 2016): 40–55. http://dx.doi.org/10.1016/j.hal.2015.11.001.

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21

WU, Haiyan, Qingyun LI, Xiaofei BING, Mengmeng GUO, Haifeng GU, Yuxiu ZHAI, and Zhijun TAN. "Metabolic regulation of azaspiracids in Chlamys farreri." Journal of Fishery Sciences of China 24, no. 6 (2017): 1298. http://dx.doi.org/10.3724/sp.j.1118.2017.17025.

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22

Oikawa, Masato, and Makoto Sasaki. "Synthetic Studies on Shellfish Toxin Azaspiracid-1." Journal of Synthetic Organic Chemistry, Japan 66, no. 9 (2008): 836–45. http://dx.doi.org/10.5059/yukigoseikyokaishi.66.836.

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23

Nguyen, Son, Jianyan Xu, and Craig J. Forsyth. "Facile biomimetic syntheses of the azaspiracid spiroaminal." Tetrahedron 62, no. 22 (May 2006): 5338–46. http://dx.doi.org/10.1016/j.tet.2006.01.112.

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24

Nicolaou, K., T. Koftis, S. Vyskocil, G. Petrovic, W. Tang, M. Frederick, D. Chen, T. Ling, Y. Li, and Y. Yamada. "Synthesis and Structural Elucidation of Azaspiracid-1." Synfacts 2006, no. 8 (August 2006): 0748. http://dx.doi.org/10.1055/s-2006-941937.

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25

Alfonso, Amparo, Mercedes R. Vieytes, Katsuya Ofuji, Masayuki Satake, K. C. Nicolaou, Michael O. Frederick, and L. M. Botana. "Azaspiracids modulate intracellular pH levels in human lymphocytes." Biochemical and Biophysical Research Communications 346, no. 3 (August 2006): 1091–99. http://dx.doi.org/10.1016/j.bbrc.2006.06.019.

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26

Rodríguez, Laura P., Natalia Vilariño, M. Carmen Louzao, Tobin J. Dickerson, K. C. Nicolaou, Michael O. Frederick, and Luis M. Botana. "Microsphere-based immunoassay for the detection of azaspiracids." Analytical Biochemistry 447 (February 2014): 58–63. http://dx.doi.org/10.1016/j.ab.2013.10.035.

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27

Jauffrais, Thierry, Christine Herrenknecht, Véronique Séchet, Manoella Sibat, Urban Tillmann, Bernd Krock, Jane Kilcoyne, et al. "Quantitative analysis of azaspiracids in Azadinium spinosum cultures." Analytical and Bioanalytical Chemistry 403, no. 3 (February 26, 2012): 833–46. http://dx.doi.org/10.1007/s00216-012-5849-2.

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28

Klontz, Karl C. "Mussel-Associated Azaspiracid Intoxication in the United States." Annals of Internal Medicine 150, no. 5 (March 3, 2009): 361. http://dx.doi.org/10.7326/0003-4819-150-5-200903030-00023.

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29

Flanagan, Andrew F., John Donlon, Roy Palmer, and Marian Kane. "Bioanalytical detection of azaspiracid, a newly discovered phycotoxin." Biochemical Society Transactions 28, no. 1 (February 1, 2000): A46. http://dx.doi.org/10.1042/bst028a046a.

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30

Nzoughet, K. J., J. T. G. Hamilton, S. D. Floyd, A. Douglas, J. Nelson, L. Devine, and C. T. Elliott. "Azaspiracid: First evidence of protein binding in shellfish." Toxicon 51, no. 7 (June 2008): 1255–63. http://dx.doi.org/10.1016/j.toxicon.2008.02.016.

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31

Tillmann, Urban, and Alfred Wegener. "Neu entdeckte Giftalge ist Ursache der Azaspiracid-Muschelvergiftung." Biologie in unserer Zeit 39, no. 3 (June 2009): 152–53. http://dx.doi.org/10.1002/biuz.200990040.

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32

Nicolaou, K. C., Petri M. Pihko, Nicole Diedrichs, Ning Zou, and Federico Bernal. "Synthesis of the FGHI Ring System of Azaspiracid." Angewandte Chemie 113, no. 7 (April 1, 2001): 1302–5. http://dx.doi.org/10.1002/1521-3757(20010401)113:7<1302::aid-ange1302>3.0.co;2-s.

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33

Nicolaou, K. C., Petri M. Pihko, Nicole Diedrichs, Ning Zou, and Federico Bernal. "Synthesis of the FGHI Ring System of Azaspiracid." Angewandte Chemie 113, no. 9 (May 4, 2001): 1621. http://dx.doi.org/10.1002/1521-3757(20010504)113:9<1621::aid-ange16213>3.0.co;2-k.

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34

Nicolaou, K. C., Wenyuan Qian, Federico Bernal, Noriaki Uesaka, Petri M. Pihko, and Jürgen Hinrichs. "Synthesis of the ABCD Ring System of Azaspiracid." Angewandte Chemie 113, no. 21 (November 5, 2001): 4192–95. http://dx.doi.org/10.1002/1521-3757(20011105)113:21<4192::aid-ange4192>3.0.co;2-0.

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35

Nicolaou, K. C., Petri M. Pihko, Nicole Diedrichs, Ning Zou, and Federico Bernal. "Synthesis of the FGHI Ring System of Azaspiracid." Angewandte Chemie International Edition 40, no. 7 (April 1, 2001): 1262–65. http://dx.doi.org/10.1002/1521-3773(20010401)40:7<1262::aid-anie1262>3.0.co;2-9.

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36

Nicolaou, K. C., Petri M. Pihko, Nicole Diedrichs, Ning Zou, and Federico Bernal. "Synthesis of the FGHI Ring System of Azaspiracid." Angewandte Chemie International Edition 40, no. 9 (May 4, 2001): 1573. http://dx.doi.org/10.1002/1521-3773(20010504)40:9<1573::aid-anie15733>3.0.co;2-d.

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37

OZAWA, MAYU. "7. Study on azaspiracid shellfish poisoning in Japan." NIPPON SUISAN GAKKAISHI 88, no. 6 (November 15, 2022): 541. http://dx.doi.org/10.2331/suisan.wa2980-7.

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38

Nicolaou, K. C., Theocharis V. Koftis, Stepan Vyskocil, Goran Petrovic, Wenjun Tang, Michael O. Frederick, David Y. K. Chen, Yiwei Li, Taotao Ling, and Yoichi M. A. Yamada. "Total Synthesis and Structural Elucidation of Azaspiracid-1. Final Assignment and Total Synthesis of the Correct Structure of Azaspiracid-1." Journal of the American Chemical Society 128, no. 9 (March 2006): 2859–72. http://dx.doi.org/10.1021/ja054750q.

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39

Vale, Carmen, Carolina Wandscheer, K. C. Nicolaou, Michael O. Frederick, Carmen Alfonso, Mercedes R. Vieytes, and Luis M. Botana. "Cytotoxic effect of azaspiracid-2 and azaspiracid-2-methyl ester in cultured neurons: Involvement of the c-Jun N-terminal kinase." Journal of Neuroscience Research 86, no. 13 (October 2008): 2952–62. http://dx.doi.org/10.1002/jnr.21731.

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40

Yadav, J. S., Sipak Joyasawal, S. K. Dutta, and A. C. Kunwar. "Stereoselective synthesis of the ABCD ring framework of azaspiracids." Tetrahedron Letters 48, no. 30 (July 2007): 5335–40. http://dx.doi.org/10.1016/j.tetlet.2007.05.021.

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41

Blanco, Juan, Fabiola Arévalo, Ángeles Moroño, Jorge Correa, Susana Muñíz, Carmen Mariño, and Helena Martín. "Presence of azaspiracids in bivalve molluscs from Northern Spain." Toxicon 137 (October 2017): 135–43. http://dx.doi.org/10.1016/j.toxicon.2017.07.025.

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42

Zhang, Zhigao, Yong Chen, Daniel Adu-Ampratwum, Antony Akura Okumu, Nathaniel T. Kenton, and Craig J. Forsyth. "Synthesis of the C22–C40 Domain of the Azaspiracids." Organic Letters 18, no. 8 (April 4, 2016): 1824–27. http://dx.doi.org/10.1021/acs.orglett.6b00557.

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43

Geraghty, J., C. Duffy, J. A. Aasen Bunæs, P. Hess, and B. Foley. "20. In vivo study of azaspiracids in mini pigs." Toxicon 91 (December 2014): 172–73. http://dx.doi.org/10.1016/j.toxicon.2014.08.028.

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44

Samdal, Ingunn A., Kjersti E. Løvberg, Lyn R. Briggs, Jane Kilcoyne, Jianyan Xu, Craig J. Forsyth, and Christopher O. Miles. "Development of an ELISA for the Detection of Azaspiracids." Journal of Agricultural and Food Chemistry 63, no. 35 (August 26, 2015): 7855–61. http://dx.doi.org/10.1021/acs.jafc.5b02513.

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45

Okumu, Antony A., and Craig J. Forsyth. "Synthesis of the C1–C19 Domain of Azaspiracid-34." Organic Letters 21, no. 2 (January 2, 2019): 356–59. http://dx.doi.org/10.1021/acs.orglett.8b03451.

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46

Kellmann, Ralf, Carlos A. M. Schaffner, Toril A. Grønset, Masayuki Satake, Mathias Ziegler, and Kari E. Fladmark. "Proteomic response of human neuroblastoma cells to azaspiracid-1." Journal of Proteomics 72, no. 4 (May 2009): 695–707. http://dx.doi.org/10.1016/j.jprot.2009.02.008.

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47

Pelin, M., S. Sosa, V. Brovedani, J. Kilcoyne, C. Nulty, P. Hess, and A. Tubaro. "In vitro effects of three azaspiracid analogues on hepatocytes." Toxicon 116 (June 2016): 85–86. http://dx.doi.org/10.1016/j.toxicon.2016.01.047.

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48

Nzoughet, Judith K., Irene R. Grant, Paulo A. Prodöhl, John T. G. Hamilton, Luis M. Botana, and Christopher T. Elliott. "Evidence of Methylobacterium spp. and Hyphomicrobium sp. in azaspiracid toxin contaminated mussel tissues and assessment of the effect of azaspiracid on their growth." Toxicon 58, no. 8 (December 2011): 619–22. http://dx.doi.org/10.1016/j.toxicon.2011.09.012.

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49

Abouabdellaha, Rachid, Asmae Bennouna, Jaouad El Attar, Katrin Erler, Mina Dellal, Abdel ghani Chafik, and Abdelatif Moukrim. "Diarrhetic shellfish poisoning toxin profile of shellfish from Southern Atlantic coasts of Morocco." South Asian Journal of Experimental Biology 1, no. 2 (April 24, 2011): 101–6. http://dx.doi.org/10.38150/sajeb.1(2).p101-106.

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During the monitoring program of phycotoxins conducted in 2005 and 2006, lipophilic shell fish toxins (LSTs) are involved in shellfish toxicity phenomena in the South Atlantic Moroccan coasts (Dakhla region). Toxicity was assessed by the traditional mouse bioassay (MBA); the content and the nature of the toxic components were established through Liquid chromatography (LC) coupled with mass spectrometry (MS). The ‘traditional’ DSP toxins group, okadaic acid (OA) and dinophysitoxins (DTXs) and their associated esters were exclusives contaminants of Dakhla’s shellfish (mussels, cockles, oysters and solen). Pectenotoxins, yessotoxins, and azaspiracids were not detected during this study. A survey of the phytoplankton community in the surrounding seawater revealed the presence of several potentially toxic species from the Dinophysis genus.
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50

Triantafyllakis, Myron, Maria Tofi, Tamsyn Montagnon, Antonia Kouridaki, and Georgios Vassilikogiannakis. "Singlet Oxygen-Mediated Synthesis of Bis-spiroketals Found in Azaspiracids." Organic Letters 16, no. 11 (May 28, 2014): 3150–53. http://dx.doi.org/10.1021/ol501301w.

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