Christopher O. Miles, Ph.D.

National Research Council Biotoxins Metrology,
Measurement Science and Standards
CanadaTel.: +1/902 402 99374
E-mail: christopher.miles@nrc-cnrc.gc.ca

Research interests

Biotoxin chemistry in general; special interest in isolation, purification and structure determination of marine toxins, fungal and plant metabolites, their semi-synthesis and derivatisation, and development of immunoassays.

Background

Background in organic chemistry from the University of Waikato/New Zealand; has been involved as lead chemist in numerous projects on fungal and plant toxin chemistry/toxicology at AgResearch Hamilton/New Zealand. Senior Scientist at the NVI Oslo on full-time basis 2009-2017. Currently Senior Scientist at National Research Council in Halifax, Canada.
 

Ongoing projects

BedreVann – Significance of cyanotoxins in Akersvannet for soil

ShellFeed – Risk assessment of algal toxins in new marine feed sources for salmon

ToxANoWa – Toxic microalgae in Norwegian waters. Uncovering fish-killing mechanisms of phytoplankton from Scandinavian waters

Recent projects

CiguaPIRE: Advancing global strategies and understanding on the origin of ciguatera fish poisoning in tropical oceans (2018-2022)

MARBioFEED – Enhanced biorefining methods for the production of marine biotoxins and microalgae fish feed (ERA-NET Marine Biotech – 2016-2019)

PROTECTED – PROTECTion against Endocrine Disruptors. Detection, mixtures, health effects, risk assessment and communication. (EU Horizon 2020, Marie Skłodowska-Curie grant, protected.eu.com – 2017-2020)

TARGET – Targeted strategies for safeguarding the noble crayfish against alien and emerging threats (NFR 243908 – 2015-2019)

ECsafeSEAFOOD – Priority environmental contaminants in seafood: safety assessment, impact and public perception (EC FP7/311820 – 2013-2016)

CYANOTOX – Monitoring of CyanoToxins in Southern Africa (NFR 196085/V10 – 2010-2015)

ALGETOX – Chemistry and chemical biology of lipophilic algal toxins (EC FP7/221117 – 2006-2010)

BIOTOX – Cost-effective tools for risk management and traceability systems for lipophilic marine biotoxins in Seafood (EC FP6/514074 – 2005-2008)

Marine algal toxins, ecology, analysis and toxicology (NFR 139593/140 – 2000-2005) Havbruk3-2005

Articles

  • Wang X, Fon M, Andersen AJC, Solhaug A, Ingebrigtsen RA, Samdal IA, Uhlig S, Miles CO, Edvardsen B and Larsen TO. Insights into the nature of ichthyotoxins from the Chrysochromulina leadbeateri blooms in Northern Norwegian fjords. Harmful Algae 2024, 137, 102681.
  • Miles CO, Strand DA, Rusch JC, Ballot A, Haande S, Løvberg KLE, Vrålstad T, Samdal IA. Microcystin profiles in European noble crayfish Astacus astacus and water in Lake Steinsfjorden, Norway. Environmental Research 2024, 242, 117623.
  • Van Hassel WHR, Abdallah MF, Velasquez MGG, Miles CO, Samdal IA, Masquelier J, et al. Experimental accumulation and depuration kinetics and natural occurrence of microcystin-LR in basil (Ocimum basilicum L.). Environ Pollut. 2024, 347, 123715.
  • Samdal IA, Sandvik M, Vu J, Sukenthirarasa MS, Kanesamurthy S, Løvberg KLE, Kilcoyne J, Forsyth CJ, Wright EJ, Miles CO. Preparation and characterization of an immunoaffinity column for the selective extraction of azaspiracids. J Chromatogr B 2022, 1207, 123360.
  • Sandvik M, Miles CO, Løvberg KLE, Kryuchkov F, Wright EJ, Mudge EM, Kilcoyne J, Samdal IA. In vitro metabolism of azaspiracids 1–3 with a hepatopancreatic fraction from blue mussels (Mytilus edulis). J Agric Food Chem 2021, 69, 11322–11335.
  • Sandvik, M.; Miles, C.O.; Wilkins, A.L.; Fæste, C. In vitro hepatic biotransformation of the algal toxin pectenotoxin-2. Toxicon: X 2020, 6, 100031.
  • Foss A, Miles CO, Samdal IA, Løvberg KE, Wilkins AL, Rise F, Jaabæk JAH, McGowan PC, Aubel MT. Analysis of free and metabolized microcystins in samples following a bird mortality event. Harmful Algae 2018, 80, 117–129.
  • Miles CO, Kilcoyne J, McCarron P, Giddings SD, Waaler T, Rundberget T, Samdal IA, Løvberg KE. Selective extraction and purification of azaspiracids from blue mussels (Mytilus edulis) using boric acid gel. Journal of Agricultural and Food Chemistry 2018, 66, 2962–2969.
  • Leonardo S, Kilcoyne J, Samdal IA, Miles CO, O’Sullivan CK, Diogene J, Campas M. Detection of azaspiracids in mussels using electrochemical immunosensors for fast screening in monitoring programs. Sensors and Actuators B: Chemical 2018, 262, 818–827.
  • Rambla-Alegre M, Miles CO, de Iglesia P, Fernandez-Tejedor M, Jacobs S, Sioen I, Verbeke W, Samdal IA, Sandvik M, Barbosa VL, Tediosi A, Madorran E, Granby K, Kotterman M, Calis T, Diogene J. “Occurrence of cyclic imines in European commercial seafood and consumers risk assessment.” Environmental Research 2018, 161, 392–398.
  • Egaas E, Samdal IA, Miles CO. “Klimaendringer kan medføre introduksjon av nye alger og bakterier”. Norsk Fiskeoppdrett 2017, 58–59.
  • Leonardo S, Rambla-Alegre M, Samdal IA, Miles CO, Kilcoyne J, Diogene J, O’Sullivan CK, Campas M. Immunorecognition magnetic supports for the development of an electrochemical immunoassay for azaspiracid detection in mussels. Biosensors & bioelectronics 2017, 92, 200–206.
  • Samdal IA, Løvberg KE, Briggs LR, Kilcoyne J, Xu J, Forsyth CJ, Miles CO. Develoment of an ELISA for the detection of azaspiracids. Journal of Agricultural and Food Chemistry 2015, 63, 7855−7861.
  • Puddick, J.; Miles, C.O.; Prinsep, M.R. Adaptation of microcystin thiol derivatization for matrix-assisted laser desorption/ionization-time of flight (MALDI-TOF) mass spectrometry analysis. Toxicon 2015, 109, 13–17.
  • Kilcoyne, J.; Twiner, M.J.; McCarron, P.; Crain, S.; Giddings, S.D.; Foley, B.; Rise, F.; Hess, P.; Wilkins, A. L.; Miles, C.O. Structure elucidation, relative LC-MS response and in vitro toxicity of azaspiracids 7−10 isolated from blue mussels (Mytilus edulis). Journal of Agricultural and Food Chemistry 2015, 63, 5083–5091.
  • Frizzell, C.; Uhlig, S.; Miles, C.O.; Verhaegen, S.; Elliott, C.T.; Eriksen, G.S.; Sørlie, M.; Ropstad, E.; Connolly, L. Biotransformation of zearalenone and zearalenols to their major glucuronide metabolites reduces estrogenic activity, Toxicology In Vitro 2015, 29, 575-581.
  • Stanic, A.; Uhlig, S.; Solhaug, A.; Rise, F.; Wilkins, A.; Miles, C.O. Nucleophilic addition of thiols to deoxynivalenol, Journal of Agricultural and Food Chemistry 2015, 63, 7556-7566.
    Samdal, I.A.; Løvberg, K.E.; Briggs, L.R.; Kilcoyne, J.; Xu, J.; Forsyth, C.J.; Miles, C.O.; Development of an ELISA for the detection of azaspiracids. Journal of Agricultural and Food Chemistry 2015, 63, 7855−7861.
  • Samdal IA, Ballot A, Løvberg KE, Miles CO. Multihapten approach leading to a sensitive ELISA with broad cross-reactivity to microcystins and nodularin. Environmental Science & Technology 2014, 48, 8035–8043.
  • Ballot, A.; Sandvik, M.; Rundberget, T.; Botha, C.J.; Miles, C.O. Diversity of cyanobacteria and cyanotoxins in Hartebeespoort Dam, South Africa. Marine and Freshwater Research 2014, 65, 175–189.
  • Kilcoyne, J.; McCarron, P.; Twiner, M.J.; Nulty, C.; Crain, S.; Quilliam, M.A.; Rise, F.; Wilkins, A.L.; Miles, C.O. Epimers of Azaspiracids: Isolation, Structural Elucidation, Relative LC-MS Response, and in Vitro Toxicity of 37-epi-Azaspiracid-1. Chemical Research in Toxicology 2014, 27, 587-600.
  • Kilcoyne, J.; Nulty, C.; Jauffrais, T.; McCarron, P.; Herve, F.; Foley, B.; Rise, F.; Crain, S.; Wilkins, A.L.; Twiner, M.J.; Hess, P.; Miles, C.O. Isolation, Structure Elucidation, Relative LC-MS Response, and in Vitro Toxicity of Azaspiracids from the Dinoflagellate Azadinium spinosum. Journal of Natural Products 2014, 77, 2465-2474.
  • Miles, C.O.; Melanson, J.E.; Ballot, A. Sulfide Oxidations for LC-MS Analysis of Methionine-Containing Microcystins in Dolichospermum flos-aquae NIVA-CYA 656. Environmental Science & Technology 2014, 48, 13307-13315.
  • Jauffrais, T.; Kilcoyne, J.; Herrenknecht, C.; Truquet, P.; Séchet, V.; Miles, C. O.; Hess, P. Dissolved azaspiracids are absorbed and metabolized by blue mussels (Mytilus edulis). Toxicon 2013, 65, 81–89.
  • Miles, C. O.; Sandvik, M.; Nonga, H. E.; Rundberget, T.; Wilkins, A. L.; Rise, F.; Ballot, A. Identification of microcystins in a Lake Victoria cyanobacterial bloom using LC-MS with thiol derivatization. Toxicon 2013, 70, 21–31.
  • Miles, C. O.; Sandvik, M.; Haande, S.; Nonga, H. E.; Ballot, A. LC-MS analysis with thiol derivatization to differentiate [Dhb7]- from [Mdha7]-microcystins: analysis of cyanobacterial blooms, Planktothrix cultures and European crayfish from Lake Steinsfjorden, Norway. Environmental Science and Technology 2013, 47 (9), 4080–4087.
  • Leighfield, T. A.; Muha, N.; Miles, C. O.; Ramsdell, J. S. Semisynthesis of radiolabeled amino acid and lipid brevetoxin metabolites and their blood elimination kinetics in C57BL/6 mice. Chemical Research in Toxicology 2013, 26 (6), 868–877.
  • Puddick, J.; Prinsep, M. R.; Wood, S. A.; Miles, C. O.; Rise, F.; Cary, S. C.; Hamilton, D. P.; Wilkins, A. L. Structural characterization of new microcystins containing tryptophan and oxidized tryptophan residues. Marine Drugs 2013, 11 (8), 3025–3045.
  • Korsnes, M. S.; Espenes, A.; Hermansen, L. C.; Loader, J. I.; Miles, C. O. Cytotoxic responses in BC3H1 myoblast cell lines exposed to 1-desulfoyessotoxin. Toxicology In Vitro 2013, 27 (6), 1962–1969.
  • Ballot, A.; Sandvik, M.; Rundberget, T.; Botha, C. J.; Miles, C. O. Diversity of cyanobacteria and cyanotoxins in Hartbeespoort Dam, South Africa. Marine and Freshwater Research, in press
    Aasen, J.A.B.; Espenes, A.; Miles, C.O.; Samdal, I.A.; Hess, P.Aune, T., Combined oral toxicity of azaspiracid-1 and yessotoxin in female NMRI mice. Toxicon 2011, 57, 909-917.
  • Rundberget, T.; Aasen, J.A.B.; Selwood, A.I.Miles, C.O., Pinnatoxins and spirolides in Norwegian blue mussels and sea water. Toxicon 2011, submitted.
  • McCarron, P.; Emteborg, H.; Nulty, C.; Rundberget, T.; Loader, J.I.; Miles, C.O.; Emons, H.; Quilliam, M.A.Hess, P., A mussel tissue certified reference material for multiple phycotoxins. Part 1: design and preparation. Analytical and Bioanalytical Chemistry 2011, 400, 821-833.
  • Selwood, A.I.; Miles, C.O.; Wilkins, A.L.; van Ginkel, R.; Munday, R.; Rise, F.McNabb, P., Isolation, structural determination, and acute toxicity of novel pinnatoxins E, F and G. Journal of Agricultural and Food Chemistry 2010, 58 (10), 65326542.
  • Miles, C.O.; Rundberget, T.; Sandvik, M.; Aasen, J.A.B.Selwood, A.I., The presence of pinnatoxins in Norwegian mussels, in National Veterinary Institute’s Report Series. 2010, National Veterinary Institute: Oslo, Norway, p10.
  • Bottein, M.-Y.D.; Fuquay, J.M.; Munday, R.; Selwood, A.I.; van Ginkel, R.; Miles, C.O.; Loader, J.I.; Wilkins, A.L.Ramsdell, J.S., Bioassay methods for detection of N-palmitoylbrevetoxin-B2 (BTX-B4). Toxicon 2010, 55 (2-3), 497-506.
  • Uhlig, S.; Botha, C.J.; Vrålstad, T.; Rolén, E.Miles, C.O., Indole–diterpenes and ergot alkaloids in Cynodon dactylon (Bermuda grass) infected with Claviceps cynodontis from an outbreak of tremors in cattle. Journal of Agricultural and Food Chemistry 2009, 57 (23), 11112–11119.
  • Rundberget, T.; Gustad, E.; Samdal, I.A.; Sandvik, M.Miles, C.O., A convenient and cost-effective method for monitoring marine algal toxins with passive samplers. Toxicon 2009, 53 (5), 543–550.
  • McCarron, P.; Kilcoyne, J.; Miles, C.O.Hess, P., Formation of azaspiracids-3, -4, -6, and -9 via decarboxylation of carboxyazaspiracid metabolites from shellfish. Journal of Agricultural and Food Chemistry 2009, 57 (1), 160–169.
  • Huhn, J.; Jeffrey, P.D.; Larsen, K.; Rundberget, T.; Rise, F.; Cox, N.R.; Arcus, V.; Shi, Y.Miles, C.O., A structural basis for the reduced toxicity of dinophysistoxin-2. Chemical Research in Toxicology 2009, 22 (11), 1782-1786.
  • di Menna, M.E.; Smith, B.L.Miles, C.O., A history of facial eczema (pithomycotoxicosis) research. New Zealand Journal of Agricultural Research 2009, 52 (4), 345-376.
    Torgersen, T.; Miles, C.O.; Rundberget, T.Wilkins, A.L., New esters of okadaic acid in seawater and blue mussels (Mytilus edulis). Journal of Agricultural and Food Chemistry 2008, 56 (20), 9628–9635.
  • Stevenson, D.E.; Hansen, R.P.; Loader, J.I.; Jensen, D.J.; Cooney, J.M.; Wilkins, A.L.Miles, C.O., Preparative enzymatic synthesis of glucuronides of zearalenone and five of its metabolites. Journal of Agricultural and Food Chemistry 2008, 56 (11), 4032–4038.
  • Selwood, A.I.; van Ginkel, R.; Wilkins, A.L.; Munday, R.; Ramsdell, J.S.; Jensen, D.J.; Cooney, J.M.Miles, C.O., Semisynthesis of S-desoxybrevetoxin-B2 and brevetoxin-B2, and assessment of their acute toxicities. Chemical Research in Toxicology 2008, 21 (4), 944–950.
  • Munday, J.S.; Thompson, D.; Finch, S.C.; Babu, J.V.; Wilkins, A.L.; Di Menna, M.E.Miles, C.O., Presumptive tremorgenic mycotoxicosis in a dog in New Zealand, after eating mouldy walnuts. New Zealand Veterinary Journal 2008, 56 (3), 145–147.
  • Espiña, B.; Louzao, M.C.; Ares, I.R.; Cagide, E.; Vieytes, M.R.; Vega, F.V.; Rubiolo, J.A.; Miles, C.O.; Suzuki, T.; Yasumoto, T.Botana, L.M., Cytoskeletal toxicity of pectenotoxins in hepatic cells. British Journal of Pharmacology 2008, 155 (6), 934–944.
  • Aune, T.; Aasen, J.A.B.; Miles, C.O.Larsen, S., Effect of mouse strain and gender on LD50 of yessotoxin. Toxicon 2008, 52 (4), 535-540.
  • Rundberget, T.; Sandvik, M.; Larsen, K.; Pizarro, G.M.; Reguera, B.; Castberg, T.; Gustad, E.; Loader, J.I.; Rise, F.; Wilkins, A.L.Miles, C.O., Extraction of microalgal toxins by large-scale pumping of sea water in Spain and Norway, and isolation of okadaic acid and dinophysistoxin-2. Toxicon 2007, 50 (7), 960–970.
  • Miles, C.O., Pectenotoxins, in Phycotoxins: Chemistry and Biochemistry, L.M. Botana, Editor. 2007, Blackwell Publishing Ltd: Oxford. pp. 159–186.
    Loader, J.I.; Hawkes, A.D.; Beuzenberg, V.; Jensen, D.J.; Cooney, J.M.; Wilkins, A.L.; Fitzgerald, J.M.; Briggs, L.R.Miles, C.O., Convenient large-scale purification of yessotoxin from Protoceratium reticulatum culture, and isolation of a novel furanoyessotoxin. Journal of Agricultural and Food Chemistry 2007, 55 (26), 11093–11100.
  • Larsen, K.; Petersen, D.; Wilkins, A.L.; Samdal, I.A.; Sandvik, M.; Rundberget, T.; Goldstone, D.; Arcus, V.; Hovgaard, P.; Rise, F.; Rehmann, N.; Hess, P.Miles, C.O., Clarification of the C-35 stereochemistries of dinophysistoxin-1 and dinophysistoxin-2 and its consequences for binding to protein phosphatase. Chemical Research in Toxicology 2007, 20 (12), 2020.
  • Larsen, K.; Petersen, D.; Wilkins, A.L.; Samdal, I.A.; Sandvik, M.; Rundberget, T.; Goldstone, D.; Arcus, V.; Hovgaard, P.; Rise, F.; Rehmann, N.; Hess, P.Miles, C.O., Clarification of the C-35 stereochemistries of dinophysistoxin-1 and dinophysistoxin-2 and its consequences for binding to protein phosphatase. Chemical Research in Toxicology 2007, 20 (6), 868–875.
  • Ares, I.R.; Louzao, M.C.; Espiña, B.; Vieytes, M.R.; Miles, C.O.; Yasumoto, T.M., B.L., Lactone ring of pectenotoxins: a key factor for their activity on cytoskeleton dynamics. Cellular Physiology and Biochemistry 2007, 19, 283–292.
  • Allingham, J.S.; Miles, C.O.Rayment, I., A structural basis for regulation of actin polymerization by pectenotoxins. Journal of Molecular Biology 2007, 371 (4), 959–970.
    Wilkins, A.L.; Rehmann, N.; Torgersen, T.; Rundberget, T.; Keogh, M.; Petersen, D.; Hess, P.; Rise, F.Miles, C.O., Identification of fatty acid esters of pectenotoxin-2 seco acid in blue mussels (Mytilus edulis) from Ireland. Journal of Agricultural and Food Chemistry 2006, 54 (15), 5672–5678.
  • Wilkins, A.L.Miles, C.O., Structure determination of new algal toxins using NMR methods. Chemistry in New Zealand 2006, 70 (3), 70–74.
  • Suzuki, T.; Walter, J.A.; LeBlanc, P.; MacKinnon, S.; Miles, C.O.; Wilkins, A.L.; Munday, R.; Beuzenberg, V.; MacKenzie, A.L.; Jensen, D.J.; Cooney, J.M.Quilliam, M.A., Identification of pectenotoxin-11 as 34S-hydroxypectenotoxin-2, a new pectenotoxin analogue in the toxic dinoflagellate Dinophysis acuta from New Zealand. Chemical Research in Toxicology 2006, 19 (2), 310–318.
  • Samdal, I.A.; Olseng, C.D.; Sandvik, M.; Miles, C.O.; Briggs, L.R.; Torgersen, T.Jensen, D.J., Profile of yessotoxin analogues in a Norwegian strain of Protoceratium reticulatum, in Molluscan Shellfish Safety. Proceedings of the 5th International Conference on Molluscan Shellfish Safety, Galway, Ireland, June 14th–18th, 2004, K. Henshilwood, et al., Editors. 2006, The Marine Institute, Rinville, Oranmore: Galway, Ireland. pp. 242–247.
  • Miles, C.O.; Wilkins, A.L.; Selwood, A.I.; Hawkes, A.D.; Jensen, D.J.; Cooney, J.M.; Beuzenberg, V.MacKenzie, A.L., Isolation of yessotoxin 32-O-[β-L-arabinofuranosyl-(5’→1″)-β-L-arabinofuranoside] from Protoceratium reticulatum. Toxicon 2006, 47 (5), 510–516.
  • Miles, C.O.; Wilkins, A.L.; Munday, J.S.; Munday, R.; Hawkes, A.D.; Jensen, D.J.; Cooney, J.M.Beuzenberg, V., Production of 7-epi-pectenotoxin-2 seco acid and assessment of its acute toxicity to mice. Journal of Agricultural and Food Chemistry 2006, 54 (4), 1530–1534.
  • Miles, C.O.; Wilkins, A.L.; Hawkes, A.D.; Jensen, D.J.; Selwood, A.I.; Beuzenberg, V.; MacKenzie, A.L.; Cooney, J.M.Holland, P.T., Isolation and identification of pectenotoxins-13 and -14 from Dinophysis acuta in New Zealand. Toxicon 2006, 48 (2), 152–159.
  • Miles, C.O.; Wilkins, A.L.; Hawkes, A.D.; Jensen, D.J.; Cooney, J.M.; Larsen, K.; Petersen, D.; Rise, F.; Beuzenberg, V.MacKenzie, A.L., Isolation and identification of a cis-C8-diol-ester of okadaic acid from Dinophysis acuta in New Zealand. Toxicon 2006, 48 (2), 195–203.
  • Miles, C.O.; Wilkins, A.L.; Hawkes, A. D.; Selwood, A.I.; Jensen, D.J.; Cooney, J.M.; Beuzenberg, V.MacKenzie, A.L., Identification of 45-hydroxy-46,47-dinoryessotoxin, 44-oxo-45,46,47-trinoryessotoxin, and 9-methyl-42,43,44,45,46,47,55-heptanor-38-en-41-oxoyessotoxin, and partial characterization of some minor yessotoxins, from Protoceratium reticulatum. Toxicon 2006, 47 (2), 229–240.
  • Forsyth, C.J.; Xu, J.; Nguyen, S.T.; Samdal, I.A.; Briggs, L.R.; Rundberget, T.; Sandvik, M.Miles, C.O., Antibodies with broad specificity to azaspiracids by use of synthetic haptens. Journal of the American Chemical Society 2006, 128 (47), 15114–15116.