Wool grease-derived α-monphydric fatty alcohols are carcinostatic depending on their branched alkyl moiety bulkiness

Anticancer Research

Volumn 16, Issue 5 A, 1996, Pages 2479-2484

  Miwa, Nobuhiko ^a   Nakamura, Shingo ^a   Nagao, Norio ^a   Naruse, Sensuke ^b   Ito, Hitoshi ^b   Takada, Yoshie ^c   Kageyama, Katsuhiro ^c  

^a PREFECTURAL UNIVERSITY OF HIROSHIMA   (Japan)

^b MIE UNIVERSITY   (Japan)

^c OSAKA CITY UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

Author keywords

Antitumor activity; GC MS analysis; Molecular hydrophobicity balance; NMR analysis; Wool fatty alcohols

Indexed keywords

ALKYL GROUP; FATTY ALCOHOL; HYDROXYL GROUP;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER SURVIVAL; CONTROLLED STUDY; EHRLICH ASCITES TUMOR; FIBROSARCOMA; HYDROPHOBICITY; INTRAPERITONEAL DRUG ADMINISTRATION; MOUSE; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CHROMATOGRAPHY, LIQUID; DRUG SCREENING ASSAYS, ANTITUMOR; FATTY ALCOHOLS; MICE; SHEEP; STRUCTURE-ACTIVITY RELATIONSHIP; WAXES; WOOL;

EID: 0029907938     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

1. Girao LA, Ruck AC, Cantrill RC, and Davidson BC: The effect of C18 fattty acids on cancer cells in culture. Anticancer Res 6: 241-244, 1986.
2. Ito H, Kasama K, Naruse S, and Shimura K: Antitumor effect of palmitoleic acid on Ehrlich ascites tumor. Cancer Lett 17: 197-203, 1982.
3. Piatak DM, and Tang PFL: Potential antineoplastic dihydroxy-fatty acids. Lipids 20: 903-907. 1985.
4. Nakamura S, Nishimura Y, Inagaki K and Miwa N: Inhibition of tumor cell growth by low boiling point-saturated fatty acids isolated by molecular distillation and reversed phase liquid chromatography of hydrolysates of uncytotoxic wool grease secreted from sheep sebaceous gland. Cancer Biochem Biophys 14: 113-121, 1994.
5. Downing DT, Kranz HZ, and Murray KE: An investigation of the aliphatic constituents of hydrolysed wool wax by gas chromatography. Semin.Dermatol 11: 162-168, 1992.
6. Komori K: Chemistry of wool greese. Kagaku 22: 27-37, 1965.
7. Pelick N, and Shigley JW: The fatty acids of degras. J Am Oil Chem Soc 44: 121-125, 1967.
8. Miwa N, Yamazaki H, and Ikari Y: Enhancement of ascorbate cytotoxicity by chelation with ferrous ions through prolonged duration of the action. Anticancer Res 6: 1033-1036, 1986.
9. Miwa N, Mizuno S, and Suitani Y: Tumor growth-inhibitory glycoprotein secreted from the mouse brain at terminal stage of the ontogeny: molecular homogeneity and requirement of the retained protein conformation for exhibition of the cytotoxic action. Biochim Biophys Acta 1034: 309-317, 1990.
10. Nishizuka Y (ed): Metabolic map, Kyoritsu Publishing, Tokyo, 1980.
11. Miwa N, Yamazaki H, Nagaoka Y, Kageyama K, Onoyama Y, Yuasa I, Otani S and Morisawa S: Altered production of the active oxygen species is involved in enhanced cytotoxic action of acylated ascorbate to tumor cells. Biochim Biophys Acta 972: 144-151, 1988.
12. Miwa N and Yamazaki H: Potentiated susceptibility of ascites tumor to acyl derivatives of ascorbate caused by balanced hydrophobicity in the molecule. Exp Cell Biol 54: 245-249, 1986.
13. Kagcyama K, Nagasawa T, Kimura S, Kobayashi T. and Kinoshita Y: Cytoxic activity of unsaturated fatty acids to lymphocytes. Canad J Biochem 58: 504-508, 1980.
14. Fujiwara F, Toda S and Imashuku S: Antitumor effect of gamma-linolenic acid on human neuroblastoma cells. Prostagl Leuk Med 23: 311-320, 1986.
15. Fujiwara F, Ikushima S, Todo S, and Imashuku S: Fatty acid modification of cultured neuroblastoma cells by gamma-linolenic acid relevant to its antitumor effects. Prostagl. Leuk Med 30: 37-49, 1987.
16. Begin ME, Ells G, and Das UN: Selected fatty acids as possible intermediates for selective Gytotoxic activity of anticancer agents involving oxygen radicals. Anticancer Res 6: 291-295, 1986.
17. Iwao T, Yoshikawa H, Takada K, and Muranishi S: Potentiation of antitumor effects of bleomycin by fusogenic lipid-surfactant mixed micelles II. Tumor-neutralizing assay for inherently bleomycin-resistant murine leukemia. Chem Pharm Bull 36: 2270-2273, 1988.
18. Yoshikawa H, Kagayama Y, and Muranishi S: Overcoming of anticancer drug resistance by unsaturated aliphatic compounds and its mechanism. Drug Deliv Syst 5: 19-22, 1990.
19. Yamada J, Itoh S, Horie S, Watanahe T, Suga T: Peroxisomal ß-oxidation of exogenously administered fatty acids in rat liver. Biochem Pharmcol 35: 4363-43618, 1986.
20. Hajra AK: Acyl dihydroxyacetone phosphate: precurser of alkyl ether. Biochem Biophys Res Commun 39: 1037-1044, 1970.
21. Wykle RL, Piantadosi C, Snyder F: The role of acyldihydroxyacetone phosphate, reduced nicotiamide adenine dinucleotide and reduced nicotiamide adenine dinucleotide phosphate in the biosynthesis of O-alkyl glycerolipids by microsomal enzymes of Ehrlich ascites tumor. J Biol Chem 247: 2944-2948, 1972.
22. Fujiki Y, Miura S and Tsukamoto T: Biogenesis of peroxisomes: analyses at molecular and cellular levels. Prot Nuc Enz 35: 1427-1437, 1990.
23. Thieringer R and Raetz CR: Peroxisome-deficient Chinese hamster ovary cells with point mutations in peroxisome assembly factor-1. J Biol Chem 268: 12631-12636, 1990.
24. Osumi T, Yokota S and Hashimoto T: Proliferation of peroxisomes and induction of peroxisomal beta-oxidation enzymes in rat hepatoma H4IIEC3 by ciprofibrate. J Biochem 108: 614-621, 1990.
25. Glauert HP, Hennig B and Chow HS: Induction of peroxisomal enzymes in cultured porcine endothelial cells by the hypolipidemic drug ciprofibrate. J Biochem Toxicol 5: 115-118, 1990.
26. Watanabe T, Horie S, Yamada J, Isaji M, Nishigaki T, Naito J, and Suga T: Species differences in the effects of bezafibrate, a hypolipidemic agent, on hepatic peroxisome-associated enzymes. Biochem Pharmacol 38: 367-371.