Synthesis of [11C] coenzyme Q-related compounds for in vivo estimation of mitochondrial electron transduction and redox state in brain.
We have studied the synthesis of [11C]2,3-dimethoxy-5-methyl-6-(10-hydroxy)-decyl-1,4-benzoquinone (idebenone) and [11C]2,3-dimethoxy-5-methyl-1,4-benzoquinone (CoQo) by methylation of their respective desmethyl precursors using [11C]CH3I for in vivo measurement of mitochondrial electron transfer and redox state. The [11C]idebenone was more lipophilic than [11C]CoQo; the latter became hydrophilic by reduction. Clearance of [11C]idebenone from mouse brain was more rapid than that of [11C]CoQo. The results indicated that modification of the isoprenoid side chain in [11C]CoQ is necessary to develop more suitable radiopharmaceuticals.
Sasaki
T
T
Positron Medical Center, Tokyo Metropolitan Institute of Gerontology, Japan. sasaki@pet.tmig.or.jp
Matuoka
N
N
Kubodera
A
A
Ishii
S
S
Goto
G
G
Senda
M
M
D000818:Animals; D016227:Benzoquinones / Q000138:chemical synthesis*; D001921:Brain / Q000378:metabolism* / Q000648:ultrastructure; D002250:Carbon Radioisotopes; D004579:Electron Transport; D051379:Mice; D008928:Mitochondria / Q000378:metabolism*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011854:Radiochemistry; D014018:Tissue Distribution; D014451:Ubiquinone / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D016227:Benzoquinones; D002250:Carbon Radioisotopes; D014451:Ubiquinone; C036619:idebenone