Christopher  Miles

My main interests are bioorganic and bioanalytical chemistry, with a focus on the chemistry of potent biologically active natural compounds, principally algal toxins. This involves isolation methods, structure elucidation (LC-MS/MS, high-field NMR), developing analytical methods, production of specific antibodies against small molecules of interest, stability studies, stable isotope labeling, and investigation of toxins’ metabolism, mechanisms of action and structure-activity relationships. I am also interested in the role of the molecules in an ecological context, and in the role of boron coordination in the structure and function of marine algal toxins.

Selected publications:

• Samdal, I. A.; Løvberg, K. E.; Kristoffersen, A. B.; Briggs, L. R.; Kilcoyne, J.; Forsyth, C. J.; Miles, C. O. A practical ELISA for azaspiracids in shellfish via development of a new plate-coating antigen. J. Agric. Food Chem. 2019, 67, 2369–2376.
• Babu, J. V.; Popay, A. J.; Miles, C. O.; Wilkins, A. L.; di Menna, M. E.; Finch, S. C. Identification and structure elucidation of janthitrems A and D from Penicillium janthinellum and determination of the tremorgenic and anti-insect activity of janthitrems A and B. J. Agric. Food Chem. 2018, 66, 13116–13125.
• Foss, A. J.; Miles, C. O.; Samdal, I. A.; Løvberg, K. E.; Wilkins, A.L.; Rise, F.; Jaabæk, J. A. H.; McGowan, P. C.; Aubel, M. T. Analysis of free and metabolized microcystins in samples following a bird mortality event. Harmful Algae 2018, 80, 117–129.
• Kilcoyne, J.; McCarron, P.; Twiner, M. J.; Rise, F.; Hess, P.; Wilkins, A. L.; Miles, C. O. Identification of 21,22-dehydroazaspiracids in mussels (Mytilus edulis) and in vitro toxicity of azaspiracid-26. .J. Nat. Prod. 2018, 81, 885–893.
• Miles, C. O.; Kilcoyne, J.; McCarron, P.; Giddings, S. D.; Waaler, T.; Rundberget, T.; Samdal, I. A.; Løvberg, K. E. Selective extraction and purification of azaspiracids from blue mussels using boric acid gel. J. Agric. Food Chem. 2018, 66, 2962–2969.
• Leonardo, S.; Kilcoyne, J.; Samdal, I. A.; Miles, C. O.; O'Sullivan, C. K.; Diogène, J.; Campàs, M. Detection of azaspiracids in mussels using electrochemical immunosensors for fast screening in monitoring programs. Sens. Actuators, B 2018, 262, 818–827.
• Kenton, N. T.; Adu-Ampratwum, D.; Okumu, A. A.; McCarron, P.; Kilcoyne, J.; Rise, F.; Wilkins, A. L.; Miles, C. O.; Forsyth, C. J. Stereochemical definition of the natural product(6R,10R,13R,14R,16R,17R,19S,20S,21R,24S,25S,28S,30S,32R,33R,34R,36S,37S,39R)-aza­spiracid-3 via total synthesis and comparative analyses. Angew. Chem. Int. Ed. 2018, 57, 810–813.
• Kenton, N. T.; Adu-Ampratwum, D.; Okumu, A. A.; Zhang, Z.; Chen, Y.; Nguyen, S.; Xu, J.; Ding, Y.; McCarron, P.; Kilcoyne, J.; Rise, F.; Wilkins, A. L.; Miles, C. O.; Forsyth, C. J. Total synthesis of (6R,10R,13R,14R,16R,17R,19S,20R,21R,24S,25S,28S,30S,32R,33R,34R, 36S,37S,39R)-azaspiracid-3 reveals non-identity with the natural product. Angew. Chem. Int. Ed. 2018, 57, 805–809.
• Miles, C. O. Rapid and convenient oxidative release of thiol-conjugated forms of microcystins for chemical analysis. Chem. Res. Toxicol. 2017, 30 (8), 1599–1608.
• Uhlig, S.; Stanic, A.; Hussain, F.; Miles, C. O. Selectivity of commercial immunoaffinity columns for modified forms of the mycotoxin 4-deoxynivalenol (DON). J. Chromatogr. B 2017, 1061–1062, 322–326.
• Uhlig, S.; Stanic, A.; Hofgaard, I. S.; Kluger, B.; Schuhmacher, R.; Miles, C. O. Glutathione conjugates of deoxynivalenol in naturally contaminated grain are primarily linked via the epoxide group.Toxins 2016, 8, 329.
• Twiner, M. J.; Doucette, G. J.; Pang, Y.; Fang, C.; Forsyth, C. J.; Miles, C. O. Structure–activity relationship studies using natural and synthetic okadaic acid/dinophysistoxin. Mar. Drugs 2016, 14, 207.