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Journal of Biochemistry Advance Access published online on October 30, 2009
Journal of Biochemistry, doi:10.1093/jb/mvp172
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© The authors 2009. Published by Oxford University Press on behalf of the Japanese Biochemical Society. All rights reserved.

Rapid Communication

Highly Amphiphilic Manganese Porphyrin for the Mitochondrial Targeting Antioxidant

Takayuki Haruyama, Shoichiro Asayama and Hiroyoshi Kawakami*

Department of Applied Chemistry, Tokyo Metropolitan University, 1-1 Minami-Osawa, Hachioji, Tokyo 192-0397, Japan

* Author to whom correspondence should be addressed: Telephone: +81-42-677-1111 (ext.) 4972. Fax: +81-42-677-2821. E-mail: kawakami-hiroyoshi{at}c.metro-u.ac.jp.

Received September 18, 2009; Accepted October 14, 2009


  Abstract

Here we communicate that the design of the antioxidant consisting of amphiphilic manganese porphyrin with one dimethylimidazolium group and three phenyl groups for mitochondrion targeting. The resulting Mn-porphyrin MnMImP3P exhibited highly partition coefficient (logPow=+4.78) as well as significant superoxide dismutase and peroxynitrite decomposition activities. Accordingly, the MnMImP3P exhibited a little increase in fluorescence intensity attributed to 3,3'-dipropyl-2,2'-thiadicarbocyanine iodide [diS-C3-(5)], a tracer dye to assess the mitochondrial membrane potential, which suggested the interaction of the MnMImP3P, leading to the release of the fluorescence dye from the mitochondrial membrane, with the mitochondria. As a result, the MnMImP3P rescued the cell death under oxidative stress concerned with mitochondrial damage.


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