Photocytotoxicity of water-soluble metalloporphyrin derivatives.
A new water-soluble porphyrin derivative, 2,4-bis(1-decyloxyethyl)-deuteroporphyrinyl-6,7-bisaspart ic acid (C10-DP), and its metal complexes (Ga, I(n), Zn, Mn, Cu, Ni and Fe) were examined for their physicochemical properties (absorption, fluorescence, triplet lifetime and partition coefficient) and photocytotoxicity on HeLa cells. The five derivatives with longer (> 1 ms) triplet lifetimes (free base, Zn, Ga, I(n) and Sn complexes) exhibited remarkable photocytotoxicity, and the other derivatives (Mn, Cu, Ni and Fe), which had or were deduced to have fairly short (< 0.01 ms) triplet lifetimes, manifested no photocytotoxicity, indicating that the triplet lifetime of these derivatives played a significant role in their photocytotoxicity. Cellular fluorescence due to C10-DP and its gallium complex was observed mainly on the plasma membrane at the concentrations showing significant photocytotoxicity with low (< 32.6%) cytotoxicity in the dark (2-10 microM).
Department of Food Science and Technology, Faculty of Agriculture, Kyoto University, Japan.
T
T
Ando
K
K
Irie
K
K
Koshimizu
T
T
Takemura
H
H
Nishino
A
A
Iwashima
N
N
Takeda
S
S
Nakajima
I
I
Sakata
D001224:Aspartic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000633:toxicity; D002455:Cell Division / Q000187:drug effects*; D003905:Deuteroporphyrins / Q000737:chemistry / Q000633:toxicity*; D006367:HeLa Cells; D006801:Humans; D008027:Light; D008051:Lipid Bilayers; D008665:Metalloporphyrins / Q000633:toxicity*; D008670:Metals / Q000633:toxicity*; D010713:Phosphatidylcholines; D017319:Photosensitizing Agents / Q000633:toxicity*; D012995:Solubility; D013057:Spectrum Analysis; D013329:Structure-Activity Relationship; D014867:Water
D003905:Deuteroporphyrins; D008051:Lipid Bilayers; D008665:Metalloporphyrins; D008670:Metals; D010713:Phosphatidylcholines; D017319:Photosensitizing Agents; D014867:Water; C081502:2,4-bis(1-decyloxyethyl)deuteroporphyrinyl-6,7-bisaspartic acid; D001224:Aspartic Acid