Relationship between lipophilicity and inhibitory activity against cancer cell growth of nine kinds of alk(en)yl trisulfides with different side chains

Oncology Research

Volumn 18, Issue 11-12, 2010, Pages 575-582

  Iitsuka, Yuji ^a   Tanaka, Yuki ^a   Hosono Fukao, Tomomi ^a   Hosono, Takashi ^a   Seki, Taiichiro ^a   Ariga, Toyohiko ^a  

^a NIHON UNIVERSITY   (Japan)

Author keywords

Colon cancer cells; Diallyl trisulfide; Dibutenyl trisulfide; Garlic; Lipophilicity

Indexed keywords

ALLYL COMPOUND; ANTINEOPLASTIC AGENT; DI-N-PROPYL TRISULFIDE; DIALLYL TRISULFIDE; DIMETHYL TRISULFIDE; DISULFIDE; METHYLALLYL TRISULFIDE; SULFIDE;

CELL PROLIFERATION; CHEMISTRY; DRUG EFFECTS; GARLIC; HT 29 CELL LINE; HUMAN; SOLUBILITY; STRUCTURE ACTIVITY RELATION;

ALLYL COMPOUNDS; ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; DISULFIDES; GARLIC; HT29 CELLS; HUMANS; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; SULFIDES;

EID: 77956913220     PISSN: 09650407     EISSN: None     Source Type: Journal    
DOI: 10.3727/096504010X12767359113965     Document Type: Article

References (39)

1. Lawson, L. The composition and chemistry of garlic cloves and processed garlic. In: Koch, H. P.; Lawson, L. D., eds. Garlic: The science and therapeutic applications of Allium sativum L. and related species, 2nd ed. Baltimore, MD: Williams & Wilkins; 1996:37-109.
2. Ariga, T.; Seki, T. Functional foods from garlic and onion. In: Shi, J.; Ho, C. T.; Shahidi, F., eds. Asian functional foods. New York: CRC Press; 2005:433-489.
3. Hosono, T.; Fukao, T.; Ogihara, J.; Ito, Y.; Shiba, H.; Seki, T.; Ariga, T. Diallyl trisulfide suppresses the proliferation and induces apoptosis of human colon cancer cells through oxidative modification of beta-tubulin. J. Biol. Chem. 280:41487-41493; 2005.
4. Fukao, T.; Hosono, T.; Misawa, S.; Seki, T.; Ariga, T. Chemoprotective effect of diallyl trisulfide from garlic against carbon tetrachloride-induced acute liver injury of rats. Biofactors 21:171-174; 2004. (Pubitemid 40921849)
5. Fukao, T.; Hosono, T.; Misawa, S.; Seki, T.; Ariga, T. The effects of allyl sulfides on the induction of phase II detoxification enzymes and liver injury by carbon tetrachloride. Food Chem. Toxicol. 42:743-749; 2004.
6. Hosono-Fukao, T.; Hosono, T.; Seki, T.; Ariga, T. Diallyl trisulfide protect rats from carbon tetrachloride-induced liver injury. J. Nutr. 139:2252-2256; 2009.
7. Koizumi, K.; Iwasaki, Y.; Narukawa, M.; Iitsuka, Y.; Fukao, T.; Seki, T.; Ariga, T.; Watanabe, T. Diallyl sulfides in garlic activate both TRPA1 and TRPV1. Biochem. Biophys. Res. Commun. 382:545-548; 2009.
8. Zhang, G.; Wu, H.; Zhu, B.; Shimoishi, Y.; Nakamura, Y.; Murata, Y. Effect of dimethyl sulfides on the induction of apoptosis in human leukemia Jurkat cells and HL-60 cells. Biosci. Biotechnol. Biochem. 72:2966-2972; 2008.
9. Hosono, T.; Hosono-Fukao, T.; Inada, K.; Tanaka, R.; Yamada, H.; Iitsuka, Y.; Seki, T.; Hasegawa, I.; Ariga, T. Alkenyl group is responsible for the disruption of microtubule network formation in human colon cancer cell line HT-29 cells. Carcinogenesis 29:1400-1406; 2008.
10. Seki, T.; Hosono, T.; Hosono-Fukao, T.; Inada, K.; Tanaka, R.; Ogihara, J.; Ariga, T. Anticancer effects of diallyl trisulfide derived from garlic. Asia Pac. J. Clin. Nutr. Suppl. 1:249-252; 2008.
11. Milligan, B.; Saville, J.; Swan, M. New syntheses of trisulphides. J. Chem. Soc. 4850-4853; 1961.
12. Partition coefficient (n-octanol/water): Shaking-flask method. OECD Guideline for the Testing of Chemicals, #107. Adopted by the Council in 1995.
13. Klein, W.; Kordel, H.; Weib, W.; Poremski, H. J. Updating of the OECD Test Guideline 107 "Partition coefficient n-cctanol/water": OECD Laboratory Intercomparison Test on the HPLC method. Chemosphere 17:361-386; 1988.
14. Partition coefficient (n-octanol/water), high performance liquid chromatography (HPLC) method. OECD guideline for the testing of chemicals, #117. Adopted by the Council in 1989.
15. Mc Duffie, B. Estimation of octanol/water partition coefficients for organic pollutants using reversed-phase HPLC. Chemosphere 10:73-83; 1981.
16. Ariga, T.; Oshiba, S.; Tamada, T. Platelet aggregation inhibitor in garlic. Lancet 1(8212):150-151; 1981.
17. Ariga, T.; Seki, T. Antithrombotic and anticancer effects of garlic-derived sulfur compounds: A review. Biofactors 26:93-103; 2006.
18. Bordia, A. Effect of garlic on human platelet aggregation in vitro. Atherosclerosis 30:355-360; 1978. (Pubitemid 9008939)
19. Makheja, A. N.; Vanderhoek, J. Y.; Bailey, J. M. Effects of onion (Allium cepa) extract on platelet aggregation and thromboxane synthesis. Prostaglandins Med. 2:413-424; 1979.
20. Oi, Y.; Kawada, Y.; Shishido, C.; Wada, K.; Kominato, Y.; Nishimura, S.; Ariga, T.; Iwai, K. Allyl-containing sulfides in garlic increase uncoupling protein content in brown adipose tissue, and noradrenaline and adrenaline secretion in rats. J. Nutr. 129:336-342; 1999.
21. Thomson, M.; Al-Qattan, K. K.; Bordia, T.; Ali, M. In cluding garlic in the diet may help lower blood glucose, cholesterol, and triglycerides. Significance of garlic and its constituents in cancer and cardiovascular disease. J. Nutr. Suppl. 136:800S-802S; 2006.
22. Chang, M. L. W.; Johnson, M. A. Effect of garlic on carbohydrate metabolism and lipid synthesis in rats. J. Nutr. 110:931-936; 1980.
23. Benavides, G. A.; Squadrito, G. L.; Mills, R. W.; Patel, H. D.; Isbell, T. S.; Patel, R. P.; Darley-Usmar, V. M.; Doeller, J. E.; Kraus, D. W. Hydrogen sulfide mediates tetrathe vasoactivity of garlic. Proc. Natl. Acad. Sci. USA 104: 17977-17982; 2007.
24. Lawson, L. D. The composition and chemistry of garlic cloves and processed garlic. In: Koch, H. P.; Lawson, L. D., eds. Garlic: The science and therapeutic application of Allium sativum L. and related species, 2nd ed. Baltimore, MD: Williams & Wilkins; 1996:37-107.
25. Lawson, L. D.; Wang, Z. Y. J. Changes in the organo-sulfur compounds released from garlic during aging in water, dilute ethanol, or dilute acetic acid. J. Toxicol. 14: 214; 1995.
26. Fujisawa, H.; Suma, K.; Origuchi, K.; Kumagai, H.; Seki, T.; Ariga, T. Biological and chemical stability of garlic-derived allicin. J. Agric. Food Chem. 56:4229-4235; 2008.
27. Fujisawa, H.; Suma, K.; Origuchi, K.; Seki, T.; Ariga, T. Thermostability of allicin determined by chemical and biological assays. Biosci. Biotechnol. Biochem. 72:2877-2883; 2008.
28. Fujisawa, H.; Watanabe, K.; Suma, K.; Origuchi, K.; Matsufuji, M.; Seki, T.; Ariga, T. Antibacterial potential of garlic-derived allicin and its cancellation by sulfhydryl compounds. Biosci. Biotechnol. Biochem. 73:1948-1955; 2009.
29. Lipinski, C. A.; Lombardo, F.; Domminy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility in drug discovery and development settings. Adv. Drug. Deliv. Rev. 46:3-26; 2001.
30. Moriguchi, I.; Hirono, S.; Liu, Q.; Nakagome, I.; Matsushita, Y. Simple method of calculating octanol/water partition coefficient. Chem. Phar. Bull. 40:127-130; 1992.
31. Streitwieser, A. Solvolytic displacement reaction. New York: McGraw-Hill; 1962:13.
32. Taylor, J. M.; Jenner, P. M.; Jones, P. M. A comparison of the toxicity of some allyl, propenyl, and propyl compounds in the rat. Toxicol. Appl. Pharmacol. 6:378-387; 1964.
33. Cheng, Y. C.; Barbara, A. D.; Sharma, R. A.; Bobek, M. Antiviral action and cellular toxicity of four thymidine analogues: 5-ethyl-, 5-vinyl-, 5-propyl-, and 5-allyl-2′-deoxyuridine. Antimicrob. Agents Chemother. 10:119-122; 1976.
34. LaHoste, G. J.; Neveu, P. J.; Mormède, P.; Le Moal, M. Hemispheric asymmetry in theeffects of cerebral cortical ablations on mitgen-induced lymphoproliferation and plasma protection levels in female rats. Brain Res. 483: 123-129; 1989. (Pubitemid 19082446)
35. Venugopal, R.; Jaiswal, A. K. Nrf1 and Nrf2 positively and c-Fos and Fra1 negatively regulate the human antioxidant response element-mediated expression of NAD(p)H: quinine oxidoreductase1 gene. Proc. Natl. Acad. Sci. USA 93:14960-14965; 1996.
36. Itoh, K.; Chiba, T.; Takahashi, S.; Ishii, T.; Igarashi, K.; Katoh, Y.; Oyake, T.; Hayashi, N.; Satoh, K.; Hatayama, I.; Yamamoto, M.; Nabeshima, Y. An Nrf2/small Maf heterodimer mediates the induction of phase II detoxifying enzyme genes through antioxidant response elements. Biochem. Biophys. Res. Commun. 236:313-322; 1997.
37. Chen, C.; Pung, D.; Leong, V.; Hebbar, V.; Shen, G.; Nair, G.; Li, W.; Kong, A. N. Induction of detoxifying enzymes by garlic organosulfur compounds through transcription factor Nrf2: Effect of chemical structure and stress signals. Free Radic. Biol. Med. 37:1578-1590; 2004.
38. Itoh, K.; Wakabayashi, N.; Katoh, Y.; Ishii, T.; Igarashi, K.; Engel, J. D.; Yamamoto, M. Keap1 represses nuclear activation of antioxidant responsive elements by Nrf2 through binding to the amino-terminal Neh2 domain. Genes Dev. 13:76-86; 1999. (Pubitemid 29045117)
39. Dinkova-Kostova, A. T.; Holtzclaw, W. D.; Cole, R. N.; Itoh, K.; Wakabayashi, N.; Katoh, Y.; Yamamoto, M.; Talalay, P. Direct evidence that sulfhydryl groups of Keap1 are the sensors regulating induction of phase 2 enzymes that protect against carcinogens and oxidants. Proc. Natl. Acad. Sci. USA 99:11908-11913; 2002.