Enhanced anti-influenza A virus activity of (-)-epigallocatechin-3-O-gallate fatty acid monoester derivatives: Effect of alkyl chain length

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 14, 2008, Pages 4249-4252

  Mori, Shuichi ^a   Miyake, Shinya ^a   Kobe, Takayoshi ^a   Nakaya, Takaaki ^b   Fuller, Stephen D ^c   Kato, Nobuo ^a   Kaihatsu, Kunihiro ^a  

^a OSAKA UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

^c UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Antivirus agent; Epigallocatechin gallate; Influenza virus; Lipase catalyzed esterification

Indexed keywords

ALKYL GROUP; EPIGALLOCATECHIN 3 O GALLATE MONOBUTYRIC ACID; EPIGALLOCATECHIN 3 O GALLATE MONOCAPRYLIC ACID; EPIGALLOCATECHIN 3 O GALLATE MONOLAURIC ACID; EPIGALLOCATECHIN 3 O GALLATE PERACETATE; EPIGALLOCATECHIN GALLATE; EPIGALLOTECHIN 3 O GALLATE MONOPALMITIC ACID; FATTY ACID DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CELL MEMBRANE PERMEABILITY; CELL VIABILITY; CONTROLLED STUDY; DRUG CYTOTOXICITY; ENZYME MECHANISM; HYDROPHILICITY; INFLUENZA VIRUS A; NONHUMAN; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; TRANSESTERIFICATION;

ANIMALS; ANTIVIRAL AGENTS; CATALYSIS; CATECHIN; CHEMISTRY, PHARMACEUTICAL; DETERGENTS; DOGS; DRUG DESIGN; FATTY ACIDS; FLAVONOIDS; INFLUENZA A VIRUS, H1N1 SUBTYPE; MODELS, CHEMICAL; PHENOLS; SOLUBILITY; WATER;

INFLUENZA A VIRUS; ORTHOMYXOVIRIDAE;

EID: 47149112921     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.02.020     Document Type: Article

References (23)

1. For example, see:. Song J.-M., Lee K.-H., and Seong B.-L. Antiviral Res. 68 (2005) 66
2. Imanishi N., Tuji Y., Katada Y., Maruhashi M., Konosu S., Mantani N., Terasawa K., and Ochiai H. Microbiol. Immunol. 46 (2002) 491
3. Nakayama M., Suzuki K., Toda M., Okubo S., Hara Y., and Shimamura T. Antiviral Res. 21 (1993) 289
4. Yamaguchi K., Honda M., Ikigai H., Hara Y., and Shimamura T. Antiviral Res. 53 (2002) 19
5. For example, see:. Taguri T., Tanaka T., and Kouno I. Biol. Pharm. Bull. 29 (2006) 2226
6. Yoda Y., Hu Z.-Q., Zhao W.-H., and Shimamura T. J. Infect. Chemother. 10 (2004) 55
7. For example, see:. Chen D., Daniel K.G., Kuhn D.J., Kazi A., Bhuiyan M., Li L., Wang Z., Wan S.B., Lam W.H., Chan T.H., and Dou Q.P. Front. Biosci. 9 (2004) 2618
8. Ahn W.S., Huh S.W., Bae S.M., Lee I.P., Lee J.M., Namkoong S.E., Kim C.K., and Sin J.I. DNA Cell Biol. 22 (2003) 217
9. Tanaka T., Kusano R., and Kouno I. Bioorg. Med. Chem. Lett. 8 (1998) 1801
10. Hong J., Lu H., Meng X., Ryu J.-H., Hara Y., and Yang C.S. Cancer Res. 62 (2002) 7241
11. Kida K., Suzuki M., Matsumoto N., Nanjo F., and Hara Y. J. Agric. Food Chem. 48 (2000) 4151
12. Lam W.H., Kazi A., Kuhn D.J., Chow L.M.C., Chan A.S.C., Dou Q.P., and Chan T.H. Bioorg. Med. Chem. 12 (2004) 5587
13. Furuta T., Hirooka Y., Abe A., Sugata Y., Ueda M., Murakami K., Suzuki T., Tanaka K., and Kan T. Bioorg. Med. Chem. Lett. 17 (2007) 3095
14. For example, see:. Nakai M., Fukui Y., Asami S., Toyoda-Ono Y., Iwashita T., Shibata H., Mitsunaga T., Hashimoto F., and Kiso Y. J. Agric. Food Chem. 53 (2005) 4593
15. Ikeda I., Tsuda K., Suzuki Y., Kobayashi M., Unno T., Tomoyori H., Goto H., Kawata Y., Imaizumi K., Nozawa A., and Kakuda T. J. Nutr. 135 (2005) 155
16. Juhel C., Armand M., Pafumi Y., Rosier C., Vandermander J., and Lairon D. J. Nutr. Biochem. 11 (2000) 45
17. +.
18. Kaihatsu, K.; Kobe, T.; Fuller, S. D.; Kato, N. PCT Int. Appl. 304788, 2006.
19. Synthesis of EGCG-C16 by a conventional chemical method: Palmitoyl chloride (216 mg, 0.785 mmol) was dropped in 50 mL tetrahydrofuran including 1 (300 mg, 0.654 mmol) and triethylamine (0.850 mmol). Reaction mixture was stirred for 24 h at 0 °C to room temperature. After removed the solvent, the residue was purified by silica gel column chromatography to give the mixture of EGCG-monopalmitate regioisomers (EGCG-C16).
20. Synthesis of 2: EGCG-peracetate (2) was synthesized by pyridine-catalyzed acetylation of EGCG using acetic anhydride according to the following literature:. Kohri T., Nanjo F., Suzuki M., Seto R., Matsumoto N., Yamakawa M., Hojo H., Hara Y., Desai D., Amin S., Conaway C.C., and Chung F.-L. J. Agric. Food Chem. 49 (2001) 1042
21. 2, the cell sheets were fixed with 5% glutaraldehyde and the overlay agarose was removed. Then, the cell sheets were stained with methylene blue solution. Plaques formed on each well were counted and the inhibitory effects of each sample on virus infection were evaluated.
22. 2. Then, after the solution was removed and the cell cultures were washed with D-PBS, 100 μL MTT solution was added to each well. After incubation for 1 h, the optical densities at 490 nm of each well were measured by 96-well plate reader.
23. -4). The following procedure was the same as the cell-based inhibition assay described above.