Chroman/catechol hybrids: synthesis and evaluation of their activity against oxidative stress induced cellular damage.
Three series of chromans substituted at positions 2 or 5 by catechol derivatives were synthesized, and their activity against oxidative stress induced cellular damage was studied. Specifically, the ability of the new molecules to protect cultured cells from H(2)O(2)-induced DNA damage was evaluated using single cell gel electrophoresis (comet assay), while the neuroprotective activity of the new compounds against oxidative stress induced programmed cell death was studied using glutamate-challanged hippocampal HT22 cells. The majority of the new compounds are stronger neuroprotectants than quercetin. 5-Substituted chroman analogues such as the caffeic acid amides 12 and 16 and the dihydrostilbene analogue 24 were the most potent against both H(2)O(2)- and glutamate-induced damage in Jurkat T cells and HT22 cells, respectively.
Koufaki
Maria
M
Institute of Organic and Pharmaceutical Chemistry, National Hellenic Research Foundation, 48 Vas. Constantinou Ave., 116 35 Athens, Greece. mkoufa@eie.gr
Theodorou
Elissavet
E
Galaris
Dimitrios
D
Nousis
Lambros
L
Katsanou
Efrosini S
ES
Alexis
Michael N
MN
D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002396:Catechols / Q000737:chemistry*; D016923:Cell Death / Q000187:drug effects; D002460:Cell Line; D002839:Chromans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004249:DNA Damage; D004353:Drug Evaluation, Preclinical; D006801:Humans; D006861:Hydrogen Peroxide / Q000494:pharmacology; D015394:Molecular Structure; D018384:Oxidative Stress / Q000187:drug effects* / Q000502:physiology; D013237:Stereoisomerism
D000975:Antioxidants; D002396:Catechols; D002839:Chromans; D006861:Hydrogen Peroxide