Abstract
We have synthesized nitroaromatic derivatives of triterpenoid betulin (lup-20(29)-ene-3 beta, 28-diol), betulin-(28)-5'-(aziridin-1-yl)-2',4'-dinitrobenzoate and betulin-(28)-5'-nitro-2'-furoate. These compounds were reduced in single-electron way by ferredoxin: NADP+ reductase and flavocytochrome b2 at rates comparable with their simple structure analogs. Besides, these compounds were substrates for DT-diaphorase. Their toxicity to bovine leukemia virus-transformed lamb fibroblast culture was partly prevented by antioxidant N,N'-diphenyl-p-phenylene diamine and desferrioxamine, indicating an involvement of oxidative stress in their cytotoxicity.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Aziridines / pharmacology
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Dicumarol / pharmacology
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Dose-Response Relationship, Drug
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Ferredoxin-NADP Reductase / metabolism
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Fibroblasts / drug effects
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Fibroblasts / virology
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Furans / chemical synthesis*
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Furans / metabolism
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Furans / pharmacology*
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Kidney / cytology
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Kidney / virology
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L-Lactate Dehydrogenase (Cytochrome)
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L-Lactate Dehydrogenase / metabolism
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Leukemia Virus, Bovine / genetics
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NAD(P)H Dehydrogenase (Quinone) / metabolism
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Nitro Compounds / chemical synthesis
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Nitro Compounds / metabolism*
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Nitro Compounds / pharmacology*
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Nitrobenzoates / chemical synthesis*
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Nitrobenzoates / metabolism
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Nitrobenzoates / pharmacology*
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Nitrofurantoin / pharmacology
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Oxidation-Reduction
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Oxidative Stress / drug effects
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Substrate Specificity
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Toxicity Tests
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Triterpenes / chemical synthesis*
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Triterpenes / chemistry*
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Triterpenes / metabolism*
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Triterpenes / pharmacology*
Substances
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Aziridines
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Furans
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Nitro Compounds
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Nitrobenzoates
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Triterpenes
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betulin-(28)-5'-(aziridin-1-yl)-2',4'-dinitrobenzoate
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betulin-(28)-5'-nitro-2'-furoate
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betulin
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tretazicar
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Dicumarol
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Nitrofurantoin
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L-Lactate Dehydrogenase
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L-Lactate Dehydrogenase (Cytochrome)
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Ferredoxin-NADP Reductase
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NAD(P)H Dehydrogenase (Quinone)