Protective actions of 5'-n-alkylated curcumins on living cells suffering from oxidative stress.
To elucidate the roles of 5'-n-alkyl chains of curcumin derivatives in their protective actions on cells against oxidative stress, we compared the efficacy of curcumin and 5'-alkylated curcumins to inhibit the peroxidation of linoleic acid and to protect rat thymocytes suffering from H2O2-induced oxidative stress with their permeation into cells. The inhibitory action of 5'-n-alkylated curcumins on lipid peroxidation increased as the length of hydrocarbon chains of 5'-n-alkylated curcumins was prolonged. This potency order was not confirmed for the protective actions of 5'-n-alkylated curcumins on cells against oxidative stress. Among 5'-alkylated curcumins, the most potent protective action was observed for 5'-n-C3H7-curcumin because it had the greatest permeation into the cells. Further increases in the length of hydrocarbon chains (up to n-C19H39) of 5'-n-alkylated curcumins greatly attenuated their protective actions by reducing their permeation into the cells.
Oyama
Y
Y
Laboratory of Cellular Signaling, Faculty of Integrated Arts and Sciences, The University of Tokushima, Japan. oyama@ias.tokushima-u.ac.jp
Masuda
T
T
Nakata
M
M
Chikahisa
L
L
Yamazaki
Y
Y
Miura
K
K
Okagawa
M
M
D000818:Animals; D000975:Antioxidants / Q000494:pharmacology; D002452:Cell Count / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D003474:Curcumin / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology*; D004996:Ethidium; D006861:Hydrogen Peroxide / Q000494:pharmacology; D019787:Linoleic Acid / Q000378:metabolism; D015227:Lipid Peroxidation / Q000187:drug effects; D016877:Oxidants / Q000494:pharmacology; D018384:Oxidative Stress; D051381:Rats; D017208:Rats, Wistar; D013194:Staining and Labeling; D013329:Structure-Activity Relationship; D013950:Thymus Gland / Q000166:cytology / Q000187:drug effects* / Q000378:metabolism
D000975:Antioxidants; D016877:Oxidants; D019787:Linoleic Acid; D006861:Hydrogen Peroxide; D004996:Ethidium; D003474:Curcumin