Highly amphiphilic manganese porphyrin for the mitochondrial targeting antioxidant.
Here, we communicate that the design of the anti-oxidant consisting of amphiphilic manganese porphyrin with one dimethylimidazolium group and three phenyl groups for mitochondrion targeting. The resulting Mn-porphyrin MnMImP(3)P exhibited high partition coefficient (logP(ow) = +4.78) as well as significant superoxide dismutase and peroxynitrite decomposition activities. Accordingly, the MnMImP(3)P exhibited a little increase in fluorescence intensity attributed to 3,3'-dipropyl-2,2'-thiadicarbocyanine iodide [diS-C(3)-(5)], a tracer dye to assess the mitochondrial membrane potential, which suggested the interaction of the MnMImP(3)P, leading to the release of the fluorescence dye from the mitochondrial membrane, with the mitochondria. As a result, the MnMImP(3)P rescued the cell death under oxidative stress concerned with mitochondrial damage.
Haruyama
Takayuki
T
Department of Applied Chemistry, Tokyo Metropolitan University, and 1-1 Minami-Osawa, Hachioji, Tokyo 192-0397, Japan.
Asayama
Shoichiro
S
Kawakami
Hiroyoshi
H
D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D052160:Benzothiazoles / Q000378:metabolism; D002232:Carbocyanines / Q000378:metabolism; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D008345:Manganese / Q000737:chemistry / Q000378:metabolism*; D008928:Mitochondria / Q000378:metabolism*; D015394:Molecular Structure; D030421:Peroxynitrous Acid / Q000737:chemistry; D011166:Porphyrins / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D013482:Superoxide Dismutase / Q000378:metabolism
D000975:Antioxidants; D052160:Benzothiazoles; D002232:Carbocyanines; D011166:Porphyrins; D030421:Peroxynitrous Acid; D008345:Manganese; C012944:3,3'-dipropyl-2,2'-thiadicarbocyanine; D013482:Superoxide Dismutase