Synthesis and evaluation of novel radioiodinated nicotinamides for malignant melanoma

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dc.contributor.authorLiu, Xen_AU
dc.contributor.authorPham, TQen_AU
dc.contributor.authorBerghofer, PJen_AU
dc.contributor.authorChapman, Jen_AU
dc.contributor.authorGreguric, Ien_AU
dc.contributor.authorMitchell, Pen_AU
dc.contributor.authorMattner, Fen_AU
dc.contributor.authorLoc'h, Cen_AU
dc.contributor.authorKatsifis, Aen_AU
dc.date.accessioned2020-03-29T23:49:53Zen_AU
dc.date.available2020-03-29T23:49:53Zen_AU
dc.date.issued2008-10-01en_AU
dc.date.statistics2020-03-20en_AU
dc.description.abstractIntroduction A series of iodonicotinamides based on the melanin-binding iodobenzamide compound N-2-diethylaminoethyl-4-iodobenzamide was prepared and evaluated for the potential imaging and staging of disseminated metastatic melanoma. Methods [123I]Iodonicotinamides were prepared by iododestannylation reactions using no-carrier-added iodine-123 and evaluated in vivo by biodistribution and competition studies and by single photon emission computed tomography (SPECT) imaging in black and albino nude mice bearing B16F0 murine melanotic and A375 human amelanotic melanoma tumours, respectively. Results The iodonicotinamides displayed low-affinity binding for σ1–σ2 receptors (Ki>300 nM). In biodistribution studies in mice, N-(2-(diethylamino)ethyl)-5-[123I]iodonicotinamide ([123I]1) exhibited the fastest and highest uptake of the nicotinamide series in the B16F0 tumour at 1 h (∼8% ID/g), decreasing slowly over time. No uptake was observed in the A375 tumour. Clearance from the animals by urinary excretion was more rapid for N-alkyl-nicotinamides than for piperazinyl derivatives. At 1 h postinjection, the urinary excretion was 66% ID for [123I]1, while the gastrointestinal tract amounted to 17% ID. Haloperidol was unable to reduce the uptake of [123I]1 in pigmented mice, indicating that this uptake was likely due to an interaction with melanin. SPECT imaging of [123I]1 in black mice bearing the B16F0 melanoma indicated that the radioactivity was predominately located in the tumour and eyes. No specific localisation was observed in nude mice bearing A375 amelanotic tumours. Conclusion These findings suggest that [123I]1, which displays high tumour uptake with rapid clearance from the body, could be a promising imaging agent for the detection of melanotic tumours. © 2008 Elsevier Inc.en_AU
dc.identifier.citationLiu, X., Pham, T. Q., Berghofer, P., Chapman, J., Greguric, I., Mitchell, P., Mattner, F., Loc'h, C., & Katsifis, A. (2008). Synthesis and evaluation of novel radioiodinated nicotinamides for malignant melanoma. Nuclear Medicine and Biology, 35(7), 769-781. doi.org/10.1016/j.nucmedbio.2008.05.011en_AU
dc.identifier.govdoc8805en_AU
dc.identifier.issn0969-8051en_AU
dc.identifier.issue7en_AU
dc.identifier.journaltitleNuclear Medicine and Biologyen_AU
dc.identifier.pagination769-781en_AU
dc.identifier.urihttps://doi.org/10.1016/j.nucmedbio.2008.05.011en_AU
dc.identifier.urihttp://apo.ansto.gov.au/dspace/handle/10238/9299en_AU
dc.identifier.volume35en_AU
dc.language.isoenen_AU
dc.publisherElsevier B.V.en_AU
dc.subjectSynthesisen_AU
dc.subjectIodine 123en_AU
dc.subjectMelanomasen_AU
dc.subjectNeoplasmsen_AU
dc.subjectSingle photon emission computed tomographyen_AU
dc.subjectLaboratory animalsen_AU
dc.titleSynthesis and evaluation of novel radioiodinated nicotinamides for malignant melanomaen_AU
dc.typeJournal Articleen_AU
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