A Pyropheophorbide Analogue Containing a Fused Methoxy Cyclohexenone Ring System Shows Promising Cancer-Imaging Ability.

A Pyropheophorbide Analogue Containing a Fused Methoxy Cyclohexenone Ring System Shows Promising Cancer-Imaging Ability. ChemMedChem. 2019 Jul 25;: Authors: Marko AJ, Dukh M, Patel NJ, Missert JR, Ohulchanskyy T, Tabaczynski WA, Ohkubo K, Fukuzumi S, Yao R, Sajjad M, Pandey RK Abstract Herein we report the synthesis, photophysical properties, positron emission tomography (PET) imaging and photodynamic therapy (PDT) efficacy of methyl 3-(1'-m-iodobenzyloxy)ethyl-3-devinyl-verdin 4 (with or without the 124 I isotope). The PET imaging ability and ex vivo biodistribution of [124 I]4 were compared with the well-studied methyl [3-(124 1'-m-iodobenzyloxy)ethyl]-3-devinyl-pyropheophorbide-a methyl ester (PET-ONCO or [124 I]2) and [18 F]fluorodeoxyglucose ([18 F]FDG) in BALB/c mice bearing colon-26 tumors. Whole-body PET images of [124 I]4 containing a fused methoxy cyclohexenone ring system showed excellent tumor contrast with time (72>48>24 h post-injection). Ex vivo biodistribution results indicate that relative to the current clinical standard [18 F]FDG and [124 I]2 in 2 % ethanol formulation, [124 I]4, at the same radioactive dose (25 μCi per mouse), showed higher tumor uptake at 24 h post-injection and longer tumor retention. In biological environments, compound 4 showed lower fluorescence and lower singlet oxygen yield than 2, which is possibly due to higher aggregation caused by the presence of a fused cyclohexenone...
Source: ChemMedChem - Category: Chemistry Authors: Tags: ChemMedChem Source Type: research