Gymnodimine (GYM), a fast-acting marine toxin, is destructive to aquaculture and human health through contaminated shellfish. The current detection methods in GYM have definite drawbacks in operation, such as the demand for delicate instruments and the consumption of time. Therefore, silver colloid was utilized as a surface-enhanced Raman scattering (SERS) desirable substrate for sensitive and rapid detection of GYM in lake and shellfish samples. The theoretical spectrum of GYM is calculated by density functional theory (DFT), and the substrate performance is evaluated by a rhodamine 6 G probe. Under the optimal SERS experimental condition calculated by the response surface methodology, the low limit of detection of 0.105 μM with R2 of 0.9873 and a broad linearity range of 0.1 - 10 μM was achieved for GYM detection. In addition, the substrate was satisfyingly applied to detect gymnodimine in the lake and shellfish matrix samples with LOD as low as 0.148 μM and 0.170 μM, respectively. These results demonstrated a promising SERS platform for detecting marine toxins in seafood for food safety and pharmaceutical research.
References
[1]
Vilariño, N., Louzao, M.C., Vieytes, M.R. and Botana, L.M. (2010) Biological Methods for Marine Toxin Detection. Analytical and Bioanalytical Chemistry, 397, 1673-1681. https://doi.org/10.1007/s00216-010-3782-9
[2]
Lopes, V., Costa, P. and Rosa, R. (2019) Effects of Harmful Algal Bloom Toxins on marine Organisms. In: Duarte, B. and Violante Caçador, M.I., Eds., Ecotoxicology of Marine Organisms, CRC Press, Boca Raton, 42-88. https://doi.org/10.1201/b22000-4
[3]
Munday, R., Towers, N.R., Mackenzie, L., Beuzenberg, V., Holland, P.T. and Miles, C.O. (2004) Acute Toxicity of Gymnodimine to Mice. Toxicon, 44, 173-178. https://doi.org/10.1016/j.toxicon.2004.05.017
[4]
Otero, A., Chapela, M.J., Atanassova, M., Vieites, J.M. and Cabado, A.G. (2011) Cyclic Imines: Chemistry and Mechanism of Action: A Review. Chemical Research in Toxicology, 24, 1817-1829. https://doi.org/10.1021/tx200182m
[5]
Stewart, M., Blunt, J.W., Munro, M.H., Robinson, W.T. and Hannah, D.J. (1997) The Absolute Stereochemistry of the New Zealand Shellfish Toxin Gymnodimine. Tetrahedron Letters, 38, 4889-4890. https://doi.org/10.1016/S0040-4039(97)01050-2
[6]
Toyofuku, H. (2006) Joint FAO/WHO/IOC Activities to Provide Scientific Advice on Marine Biotoxins (Research Report). Marine Pollution Bulletin, 52, 1735-1745. https://doi.org/10.1016/j.marpolbul.2006.07.007
[7]
Kharrat, R., Servent, D., Girard, E., Ouanounou, G., Amar, M., Marrouchi, R., Benoit, E. and Molgo, J. (2008) The Marine Phycotoxin Gymnodimine Targets Muscular and Neuronal Nicotinic Acetylcholine Receptor Subtypes with High Affinity. Journal of Neurochemistry, 107, 883-1168. https://doi.org/10.1111/j.1471-4159.2008.05677.x
[8]
Chatzianastasiou, M., Katikou, P., Zacharaki, T., Papazachariou, A. and McKevitt, A. (2011) Cyclic Imines, as Emerging Marine Toxins: Chemical Properties, Distribution, Toxicological Aspects and Detection Methods. Journal of the Hellenic Veterinary Medical Society, 62, 240-248. https://doi.org/10.12681/jhvms.14856
[9]
Fang, L., Yao, X., Wang, L. and Li, J. (2015) Solid-Phase Extraction-Based Ultra-Sensitive Detection of Four Lipophilic Marine Biotoxins in Bivalves by High-Performance Liquid Chromatography-Tandem Mass Spectrometry. Journal of Chromatographic Science, 53, 373-379. https://doi.org/10.1093/chromsci/bmu054
[10]
Liu, Y., Yu, R.C., Kong, F.Z., Li, C., Dai, L., Chen, Z.F. and Zhou, M.J. (2017) Lipophilic Marine Toxins Discovered in the Bohai Sea Using High Performance Liquid Chromatography Coupled with Tandem Mass Spectrometry. Chemosphere, 183, 380-388. https://doi.org/10.1016/j.chemosphere.2017.05.073
[11]
Rodríguez, I., Vieytes, M.R. and Alfonso, A. (2017) Analytical Challenges for Regulated Marine Toxins. Detection Methods. Current Opinion in Food Science, 18, 29-36. https://doi.org/10.1016/j.cofs.2017.10.008
[12]
Rodriguez, L.P., Vilarino, N., Molgo, J., Araoz, R., Antelo, A., Vieytes, M.R. and Botana, L.M. (2011) Solid-Phase Receptor-Based Assay for the Detection of Cyclic Imines by Chemiluminescence, Fluorescence, or Colorimetry. Analytical Chemistry, 83, 5857-5863. https://doi.org/10.1021/ac200423s
[13]
Rodriguez, L.P., Vilarino, N., Molgo, J., Araoz, R., Carmen Louzao, M., Taylor, P., Talley, T. and Botana, L.M. (2013) Development of a Solid-Phase Receptor-Based Assay for the Detection of Cyclic Imines Using a Microsphere-Flow Cytometry System. Analytical Chemistry, 85, 2340-2347. https://doi.org/10.1021/ac3033432
[14]
Vilarino, N., Fonfria, E.S., Molgo, J., Araoz, R. and Botana, L.M. (2009) Detection of Gymnodimine-A and 13-Desmethyl C Spirolide Phycotoxins by Fluorescence Polarization. Analytical Chemistry, 81, 2708-2714. https://doi.org/10.1021/ac900144r
[15]
Fleischmann, M., Hendra, P.J. and McQuillan, A.J. (1974) Raman Spectra of Pyridine Adsorbed at a Silver Electrode. Chemical Physics Letters, 26, 163-166. https://doi.org/10.1016/0009-2614(74)85388-1
[16]
Zhang, D., Liang, P., Chen, W.W., Tang, Z.X., Li, C., Xiao, K.Y., Jin, S.Z., Ni, D.J. and Yu, Z. (2021) Rapid Field Trace Detection of Pesticide Residue in Food Based on Surface-Enhanced Raman Spectroscopy. Microchimica Acta, 188, Article No. 370. https://doi.org/10.1007/s00604-021-05025-3
[17]
Tong, Q., Wang, W.J., Fan, Y.N. and Dong, L. (2018) Recent Progressive Preparations and Applications of Silver-Based SERS Substrates. TrAC Trends in Analytical Chemistry, 106, 246-258. https://doi.org/10.1016/j.trac.2018.06.018
[18]
Lopez-Lorente, A.I. (2021) Recent Developments on Gold Nanostructures for Surface Enhanced Raman Spectroscopy: Particle Shape, Substrates and Analytical Applications. A review. Analytica Chimica Acta, 1168, Article ID: 338474. https://doi.org/10.1016/j.aca.2021.338474
[19]
Markin, A.V., Markina, N.E., Popp, J. and Cialla-May, D. (2018) Copper Nanostructures for Chemical Analysis Using Surface-Enhanced Raman Spectroscopy. TrAC Trends in Analytical Chemistry, 108, 247-259. https://doi.org/10.1016/j.trac.2018.09.004
[20]
Ding, S.Y., Yi, J., Li, J.F., Ren, B., Wu, D.Y., Panneerselvam, R. and Tian, Z.Q. (2016) Nanostructure-Based Plasmon-Enhanced Raman Spectroscopy for Surface Analysis of Materials. Nature Reviews Materials, 1, Article No. 16021. https://doi.org/10.1038/natrevmats.2016.21
[21]
Wu, D.Y., Li, J.F., Ren, B. and Tian, Z.Q. (2008) Electrochemical Surface-Enhanced Raman Spectroscopy of Nanostructures. Chemical Society Reviews, 37, 1025-1041. https://doi.org/10.1039/b707872m
[22]
Olson, T.Y., Schwartzberg, A.M., Liu, J.L. and Zhang, J.Z. (2011) Raman and Surface-Enhanced Raman Detection of Domoic Acid and Saxitoxin. Applied Spectroscopy, 65, 159-164. https://doi.org/10.1366/10-05910
[23]
Huai, Q.Y., Gao, C.L., Miao, J.L., Yao, H.L. and Wang, Z.L. (2013) Fast Detection of Saxitoxin Using Laser Tweezers Surface Enhanced Raman Spectroscopy. Analytical Methods, 5, 6870-6873. https://doi.org/10.1039/c3ay41504j
[24]
Müller, C., Glamuzina, B., Pozniak, I., Weber, K., Cialla, D., Popp, J. and Cîntă Pînzaru, S. (2014) Amnesic Shellfish Poisoning Biotoxin Detection in Seawater Using Pure or Amino-Functionalized Ag Nanoparticles and SERS. Talanta, 130, 108-115. https://doi.org/10.1016/j.talanta.2014.06.059
[25]
Cao, C., Li, P., Liao, H., Wang, J., Tang, X. and Yang, L. (2020) Cys-Functionalized AuNP Substrates for Improved Sensing of the Marine Toxin STX by Dynamic Surface-Enhanced Raman Spectroscopy. Analytical and Bioanalytical Chemistry, 412, 4609-4617. https://doi.org/10.1007/s00216-020-02710-9
[26]
Cheng, S., Zheng, B., Yao, D., Wang, Y., Tian, J., Liu, L., Liang, H. and Ding, Y. (2019) Determination of Saxitoxin by Aptamer-Based Surface-Enhanced Raman Scattering. Analytical Letters, 52, 902-918. https://doi.org/10.1080/00032719.2018.1505900
[27]
Zhao, P., Liu, H., Zhu, P., Ge, S., Zhang, L., Zhang, Y. and Yu, J. (2021) Multiple Cooperative Amplification Paper SERS Aptasensor Based on AuNPs/3D Succulent-Like Silver for Okadaic Acid Quantization. Sensors and Actuators B: Chemical, 344, Article ID: 130174. https://doi.org/10.1016/j.snb.2021.130174
[28]
Lee, P.C. and Meisel, D. (1982) Adsorption and Surface-Enhanced Raman of Dyes on Silver and Gold Sols. The Journal of Physical Chemistry C, 86, 3391-3395. https://doi.org/10.1021/j100214a025
[29]
Dendisová-Vyškovská, M., Prokopec, V., Člupek, M. and Matějka, P. (2012) Comparison of SERS Effectiveness of Copper Substrates Prepared by Different Methods: What Are the Values of Enhancement Factors? Journal of Raman Spectroscopy, 43, 181-186. https://doi.org/10.1002/jrs.3022
[30]
McFarland, A.D., Young, M.A., Dieringer, J.A. and Van Duyne, R.P. (2005) Wavelength-Scanned Surface-Enhanced Raman Excitation Spectroscopy. The Journal of Physical Chemistry B, 109, 11279-11285. https://doi.org/10.1021/jp050508u
[31]
Agnihotri, S., Mukherji, S. and Mukherji, S. (2014) Size-Controlled Silver Nanoparticles Synthesized over the Range 5-100 nm Using the Same Protocol and Their Antibacterial Efficacy. RSC Advances, 4, 3974-3983. https://doi.org/10.1039/C3RA44507K
[32]
Bhui, D.K., Bar, H., Sarkar, P., Sahoo, G.P., De, S.P. and Misra, A. (2009) Synthesis and UV—Vis Spectroscopic Study of Silver Nanoparticles in Aqueous SDS Solution. Journal of Molecular Liquids, 145, 33-37. https://doi.org/10.1016/j.molliq.2008.11.014
[33]
Yang, L., Hu, J., He, L., Tang, J., Zhou, Y., Li, J. and Ding, K. (2017) One-Pot Synthesis of Multifunctional Magnetic N-Doped Graphene Composite for SERS Detection, Adsorption Separation and Photocatalytic Degradation of Rhodamine 6G. Chemical Engineering Journal, 327, 694-704. https://doi.org/10.1016/j.cej.2017.06.162
[34]
Seney, C.S., Gutzman, B.M. and Goddard, R.H. (2009) Correlation of Size and Surface-Enhanced Raman Scattering Activity of Optical and Spectroscopic Properties for Silver Nanoparticles. The Journal of Physical Chemistry C, 113, 74-80. https://doi.org/10.1021/jp805698e
[35]
Boca, S.C., Farcau, C. and Astilean, S. (2009) The Study of Raman Enhancement Efficiency as Function of Nanoparticle Size and Shape. Nuclear Instruments and Methods in Physics Research Section B: Beam Interactions with Materials and Atoms, 267, 406-410. https://doi.org/10.1016/j.nimb.2008.10.020
[36]
Wang, S., Yan, X., Zhang, M., Dong, G., Moro, R., Ma, Y. and Ma, L. (2022) Real-Time Size Tuning and Measuring of Silver Nanoparticles by Cyclic voltamMetry and Raman Spectroscopy. Materials Letters, 310, Article ID: 131420. https://doi.org/10.1016/j.matlet.2021.131420
[37]
Pustovit, V.N. and Shahbazyan, T.V. (2005) Quantum-Size Effects in SERS from Noble-Metal Nanoparticles. Microelectronics Journal, 36, 559-563. https://doi.org/10.1016/j.mejo.2005.02.069
[38]
Park, S.G., Mun, C., Xiao, X., Braun, A., Kim, S., Giannini, V., Maier, S.A. and Kim, D.H. (2017) Surface Energy-Controlled SERS Substrates for Molecular Concentration at Plasmonic Nanogaps. Advanced Functional Materials, 27, Article ID: 1703376. https://doi.org/10.1002/adfm.201703376
[39]
Jiang, Y., Wang, J., Malfatti, L., Carboni, D., Senes, N. and Innocenzi, P. (2018) Highly Durable Graphene-Mediated Surface Enhanced Raman Scattering (G-SERS) Nanocomposites for Molecular Detection. Applied Surface Science, 450, 451-460. https://doi.org/10.1016/j.apsusc.2018.04.218
[40]
Huang, C.C. and Chen, W. (2018) A SERS Method with Attomolar Sensitivity: A Case Study with the Flavonoid Catechin. Microchimica Acta, 185, Article No. 120. https://doi.org/10.1007/s00604-017-2662-9
[41]
Medhioub, A., Medhioub, W., Amzil, Z., Sibat, M., Bardouil, M., Ben Neila, I., Mezghani, S., Hamza, A., Lassus, P. (2009) Influence of Environmental Parameters on Karenia Selliformis Toxin Content in Culture. Cahiers de Biologie Marine, 50, 333-342.
[42]
Kamal, S. and Yang, T.C.K. (2022) A Novel Ag2SO3 Microcrystal Substrate for Highly Sensitive SERS Sensing of Multifold Organic Pollutants. Journal of Alloys and Compounds, 898, Article ID: 162919. https://doi.org/10.1016/j.jallcom.2021.162919
[43]
Kim, J.A., Wales, D.J., Thompson, A.J. and Yang, G.Z. (2020) Fiber-Optic SERS Probes Fabricated Using Two-Photon Polymerization for Rapid Detection of Bacteria. Advanced Optical Materials, 8, Article ID: 1901934. https://doi.org/10.1002/adom.201901934
[44]
Cong, S., Wang, Z., Gong, W.B., Chen, Z.G., Lu, W.B., Lombardi, J.R. and Zhao, Z.G. (2019) Electrochromic Semi-conductors as Colorimetric SERS Substrates with High Reproducibility and Renewability. Nature Communications, 10, Article No. 678. https://doi.org/10.1038/s41467-019-08656-6
[45]
Zhang, P., Gao, J. and Sun, X.H. (2015) An Ultrasensitive, Uniform and Large-Area Surface-Enhanced Raman Scattering Substrate Based on Ag or Ag/Au Nanoparticles Decorated Si Nanocone Arrays. Applied Physics Letters, 106, Article ID: 043103. https://doi.org/10.1063/1.4906800
