Biological Activity of p-Methylaminophenol, an Essential Structural Component of N-(4-Hydroxyphenyl)retinamide, Fenretinide.
スポンサーリンク
概要
- 論文の詳細を見る
Fenretinide, N-(4-hydroxyphenyl) retinamide (4-HPR), is a synthetic amide of all-trans-retinoic acid (RA), which inhibits cell growth, induces apoptosis, and is an antioxidant, and cancer chemopreventive and antiproliferative agent. These findings led us to investigate which structural component of 4-HPR contributes to these potent activities. Our approach was to examine 4-aminophenol (4-AP), p-methylaminophenol (p-MAP), and p-acetaminophen (p-AAP). It was found that vitamin E, 4-AP and p-MAP scavenge α, α-diphenyl-β-picrylhydrazyl (DPPH) radicals in a 1:2 ratio, in contrast to 4-HPR and p-AAP, for which 1:1 and 1:0.5 ratios were observed relative to DPPH radicals. However, RA was inactive. Lipid peroxidation in rat liver microsomes was reduced by compounds (RA>p-MAP=4-HPR>4-AP) in a dose-dependent manner, while p-AAP was inactive. In addition, both p-MAP and 4-HPR are potent inhibitors of cell growth and inducers of apoptosis in HL60 cells. p-MAP exhibits the same level of antiproliferative activity as 4-HPR against HL60R cells, which are a resistant clone against RA, and it inhibits the growth of various cancer cell lines (MCF-7, MCF-7/AdrR, HepG2, and DU-145) to an extent greater than 4-AP and p-AAP, but is less potent than 4-HPR. Thus, although the antioxidant activity of p-MAP is more potent than that of 4-HPR, p-MAP is less potent than 4-HPR in anticancer activity. These results suggest that both the anticancer and antioxidative activities shown by 4-HPR are due to the structure of p-MAP. The retinoyl residue or long alkyl chain substituent attached to an aminophenol may be significant for anticancer properties.
- 社団法人 日本生化学会の論文
著者
-
Takahashi Noriko
Department Of Biochemistry University Of Shizuoka School Of Pharmaceutical Sciences Core Research Fo
-
Fukui Tetsuya
Department Of Health Chemistry
-
TOGASHI Shin-ichi
Department of Health Chemistry, Faculty of Pharmaceutical Sciences, Hoshi University
-
Ohba Toshihiro
Department Of Health Chemistry Faculty Of Pharmaceutical Sciences Hoshi University
-
Togashi Shin-ichi
Department Of Health Chemistry Faculty Of Pharmaceutical Sciences Hoshi University
関連論文
- Identification and Characterization of Carbohydrate Molecules in Mammalian Cells Recognized by Dengue Virus Type 2
- lnhibitory action of sulfatide a putative ligand for L-selectiv on B cell proliferation and lg prodrction
- Differential Effects of Two Types of Obesity on Ketone Body Utilization in Skeletal Muscle
- Effects of Development on Acetoacetyl-CoA Synthetase Biosynthesis in Rat Liver
- Combination of RET siRNA and irinotecan inhibited the growth of medullary thyroid carcinoma TT cells and xenografts via apoptosis
- P-564 MULTI-DIMENSIONAL HPLC MAPPING METHOD FOR STRUCTURAL ANALYSES OF N-GLYCANS AND ITS APPLICATIONS TO N-GLYCOSYLATION PROFILING OF ORGANISMS AND TISSUES
- The Distribution of mRNA Expression and Protein after Hydrodynamic Injection of Transgene in Mice(Biopharmacy)
- Contribution of Glutathione Peroxidase and Nitric Oxide to Potassium Bromate-Induced Oxidative Stress and Kidney Damage in Mice
- L-Tryptophan as an Antioxidant in Human Placenta Extract
- Antioxidant Properties of a New Type of Polyene, Falconensone A and Its Derivatives
- Induction of Apoptosis in the Human Promyelocytic Leukemia Cell Line HL60 by Falconensone A and Its Derivatives, New Polyenes
- Suppressive Effects of Uracil, Tyrosine, and Phenylalanine Contained in Human-Placenta Extract on Acute Ethanol-Induced Liver Injury in Mice
- Purification and Identification of Antioxidant Substances in Human-Placenta Extracts
- Studies on the Suppressive Effect of Antioxidant in Human Placental Extract on Oxidative Stress and its Mechanism(PROCEEDINGS OF 24TH SYMPOSIUM ON TOXICOLOGY AND ENVIRONMENTAL HEALTH)
- IL-4とIL-7によるヒトナイーブT細胞のCD31発現とIL-4産生の調節
- Association of Liposomes Containing a Soybean-Derived Sterlyglucoside Mixture with Rat Primary Cultured Hepatocytes
- Formation of Retinoyl-CoA in Rat Tissues
- Identification of Multiple Regulatory Elements of Human L-Histidine Decarboxylase Gene
- Cerebral Oxidative Stress and Mitochondrial Dysfunction in Oxonate-Induced Hyperuricemic Mice
- Contribution of Nitric Oxide to Potassium Bromate-Induced Elevation of Methaemoglobin Concentration in Mouse Blood(Toxicology)
- Allelotype Analysis in Mouse Hepatocellular Carcinomas; Frequent Homozygous Deletion of Mouse Homolog of p16/CDKN2 Gene on Chromosome 4 in Culture
- Potassium Bromate-lnduced Hyperuricemia Stimulates Acute Kidney Damage and Oxidative Stress
- Biological Activity of p-Methylaminophenol, an Essential Structural Component of N-(4-Hydroxyphenyl)retinamide, Fenretinide
- Effect of Human Placenta Extract on Potassium Oxonate-Induced Elevation of Blood Uric Acid Concentration
- Considerations for Accurate Whole Plant Photosynthesis Measurement
- C-reactive protein is associated with cigarette smoking-induced hyperfiltration and proteinuria in an apparently healthy population
- Antioxidant Properties of N-(4-Hydroxyphenyl)retinamide (Fenretinide)
- Unique heparan sulfate from shrimp heads exhibits a strong inhibitory effect on infections by dengue virus and Japanese encephalitis virus
- Characterization of Photosynthetic Glycogen and α-Glucosidase from Thermophilic Cyanobacteria, Lyngbya-Phormidium-Plectonema Group B
- Glycogen as Primordial Carbon Reserve and α-Glucosidase in the Genera Lyngbya-Phormidium-Plectonema, Thermophilic Cyanobacteria
- Suppressive Effect of Curcumin on Trichloroethylene-induced Oxidative Stress
- The Role of Acetoacetyl-CoA Synthetase, a Ketone Body-Utilizing Enzyme, in 3T3-L1 Adipocyte Differentiation
- Comparison of serum ferritin and oxidative stress biomarkers between Japanese workers with and without metabolic syndrome
- Pioglitazone enhances small-sized adipocyte proliferation in subcutaneous adipose tissue
- Biological Activity of p-Methylaminophenol, an Essential Structural Component of N-(4-Hydroxyphenyl)retinamide, Fenretinide.