Synthesis of rhodamine-labelled dieckol: its unique intracellular localization and potent anti-inflammatory activity

Chemical Communications

Volumn 50, Issue 86, 2014, Pages 13045-13048

  Kwak, Jong Hwan ^a   He, Yanxia ^b   Yoon, Byungkwon ^b   Koo, Seyoung ^b   Yang, Zhigang ^b   Kang, Eun Ju ^c   Lee, Bong Ho ^d   Han, Seung Yun ^c   Yoo, Yung Choon ^c   Lee, Kyung Bok ^c   Kim, Jong Seung ^b  

^a Sungkyunkwan University   (South Korea)

^b Korea University   (South Korea)

^c Konyang University   (South Korea)

^d Hanbat National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFLAMMATORY AGENT; BENZOFURAN DERIVATIVE; DIECKOL; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INTERLEUKIN 6; LIPOPOLYSACCHARIDE; MITOGEN ACTIVATED PROTEIN KINASE; NITRIC OXIDE; RHODAMINE; TUMOR NECROSIS FACTOR ALPHA; POLYPHENOL DERIVATIVE; RHODAMINE B; UNCLASSIFIED DRUG;

ANIMAL; CELL LINE; CHEMISTRY; CONFOCAL MICROSCOPY; CYTOLOGY; DRUG EFFECTS; ENDOPLASMIC RETICULUM; MACROPHAGE; METABOLISM; MOUSE; SYNTHESIS; ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CELL STIMULATION; CLICK CHEMISTRY; CONFOCAL LASER MICROSCOPY; CYTOKINE PRODUCTION; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME PHOSPHORYLATION; INTRACELLULAR SIGNALING; MITOCHONDRION; NONHUMAN; PROTEIN EXPRESSION;

ANIMALS; ANTI-INFLAMMATORY AGENTS; BENZOFURANS; CELL LINE; ENDOPLASMIC RETICULUM; INTERLEUKIN-6; LIPOPOLYSACCHARIDES; MACROPHAGES; MICE; MICROSCOPY, CONFOCAL; MITOGEN-ACTIVATED PROTEIN KINASES; NF-KAPPA B; NITRIC OXIDE; RHODAMINES; TUMOR NECROSIS FACTOR-ALPHA;

EID: 84907736376     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc04270k     Document Type: Article

References (43)

1. K. W. Glombitza, H. P. Vogels, Planta Med., 1985, 51, 308.
2. H. S. Kang, H. Y. Chung, J. H. Jung, B. W. Son, J. S. Choi, Chem. Pharm. Bull., 2003, 51, 1012.
3. T. Shibata, K. Ishimaru, S. kawaguchi, H. Yoshikawa, Y. Hama, J. Appl. Phycol., 2008, 20, 705.
4. A.-R. Kim, T.-S. Shin, M.-S. Lee, J.-Y. Park, K.-E. Park, N.-Y. Yoon, J.-S. Kim, J.-S. Choi, B.-C. Jang, D.-S. Byun, N.-K. Park, H.-R. Kim, J. Agric. Food Chem., 2009, 57, 3483.
5. H. A. Jung, S. E. Jin, B. R. Ahn, C. M. Lee, J. S. Choi, Food Chem. Toxicol., 2013, 59, 199.
6. Y. Li, Z.-J. Qian, B. H. Ryu, S.-H. Lee, M.-M. Kim, S.-K. Kim, Bioorg. Med. Chem., 2009, 17, 1963.
7. T.-H. Kwon, T.-W. Kim, C.-G. Kim, N.-H. Park, J. Food Sci., 2013, 78, C679.
8. M.-C. Kang, S.-M. Kang, G. Ahn, K.-N. Kim, N. Kang, K. W. Samarakoon, M.-C. Oh, J.-S. Lee, Y.-J. Jeon, Environ. Toxicol. Pharmacol., 2013, 35, 517.
9. M.-C. Kang, C. Ahn, X. Yang, K.-N. Kim, S.-M. Kang, S.-H. Lee, S.-C. Ko, J.-Y. Ko, D. Kim, Y.-T. Kim, Y. Jee, S.-J. Park, Y.-J. Jeon, Food Chem. Toxicol., 2012, 50, 1986.
10. M.-C. Kang, W. A. J. P. Wijesinghe, S.-H. Lee, S.-M. Kang, S.-C. Ko, X. Yang, N. Kang, B.-T. Jeon, J. Kim, D.-H. Lee, Y.-J. Jeon, Food Chem. Toxicol., 2013, 53, 294.
11. S.-H. Lee, K.-H. Min, J.-S. Han, D.-H. Lee, D.-B. Park, W.-K. Jung, P.-J. Park, B.-T. Jeon, S.-K. Kim, Y.-J. Jeon, Food Chem. Toxicol., 2012, 50, 575.
12. Q.-T. Le, Y. Li, Z.-J. Qian, M.-M. Kim, S.-K. Kim, Process Biochem., 2009, 44, 168.
13. H.-J. Kwon, Y. B. Ryu, Y.-M. Kim, N. Song, C. Y. Kim, M.-C. Rho, J.-H. Jeong, K.-O. Cho, W. S. Lee, S.-J. Park, Bioorg. Med. Chem., 2013, 21, 4706.
14. Y. B. Ryu, H. J. Jeong, S. Y. Yoon, J.-Y. Park, Y. M. Kim, S.-J. Park, M.-C. Rho, S.-J. Kim, W. S. Lee, J. Agric. Food Chem., 2011, 59, 6467.
15. J.-S. Yoon, A. K. Yadunandam, S.-J. Kim, H.-C. Woo, H.-R. Kim, G.-D. Kim, J. Nat. Med., 2013, 67, 519.
16. Y. Li, Z.-J. Qian, M.-M. Kim, S.-K. Kim, J. Food Biochem., 2011, 35, 357.
17. D. Lindholm, H. Wootz, L. Korhonen, Cell Death Differ., 2006, 13, 385.
18. C. Hetz, B. Mollereau, Nat. Rev. Neurosci., 2014, 15, 233.
19. G. S. Hotamisligil, Cell, 2010, 140, 900.
20. A. D. Garg, A. Kgnieszka, O. Krysko, P. Vandenabeele, D. V. Krysko, P. Agostinis, Trends Mol. Med., 2012, 18, 589.
21. S. Z. Hasnain, R. Lourie, I. Das, A. C.-H. Chen, M. A. McGuckin, Immunol. Cell Biol., 2012, 90, 260.
22. T. Lawrence, D. A. Willoughby, D. W. Gilroy, Nat. Rev. Immunol., 2002, 2, 787.
23. K. S. Lau, R. W. Grange, E. Isotani, I. H. Sarelius, K. E. Kamm, P. L. Huang, J. T. Stull, Physiol. Genomics, 2000, 2, 21.
24. R. Zamora, Y. Vodovotz, T. R. Billiar, Mol. Med., 2000, 6, 347.
25. B. Hinz, K. Brune, J. Pharmacol. Exp. Ther., 2002, 300, 67.
26. A. T. Hoye, J. E. Davoren, P. Wipf, Acc. Chem. Res., 2008, 41, 87.
27. L. F. Mottram, S. Forbes, B. D. Ackley, B. R. Peterson, Beilstein J. Org. Chem., 2012, 8, 2156.
28. P. Reungpatthanaphong, S. Dechsupa, J. Meesungnoen, C. Loetchutinat, S. Mankhetkorn, J. Biochem. Biophys. Methods, 2003, 57, 1.
29. C. Xie, J. Chang, X.-D. Hao, J.-M. Yu, H.-R. Liu, X. Sun, Eur. J. Pharm. Biopharm., 2013, 85, 541.
30. Y. Lu, S.-J. Suh, C.-H. Kwak, K.-M. Kwon, C.-S. Seo, Y. Li, Y. Jin, X. Li, S.-L. Hwang, O. Kwon, Y.-C. Chang, Y.-G. Park, S.-S. Park, J.-K. Son, C.-H. Kim, H. W. Chang, Int. Immunopharmacol., 2012, 12, 175.
31. V. D. La, F. Lazzarin, D. Ricci, D. Fraternale, S. Genovese, F. Epifano, D. Grenier, Phytother. Res., 2010, 24, 1687.
32. A. Demoule, M. Divangahi, L. Yahiaoui, G. Danialou, D. Gvozdic, K. Labbe, W. Bao, B. J. Petrof, Am. J. Respir. Crit. Care Med., 2006, 174, 646.
33. H. Yoshida, FEBS J., 2007, 274, 630.
34. M. Kitamura, Int. Rev. Immunol., 2011, 30, 4.
35. T. Yamazaki, M. Muramoto, T. Oe, N. Morikawa, O. Okitsu, T. Nagashima, S. Nishimura, Y. Katayama, Y. Kita, Neuropharmacology, 2006, 50, 558.
36. G. Begum, L. Harvey, C. E. Dixon, D. Sun, Transl. Stroke Res., 2013, 4, 635.
37. J. S. Kim, R. W. Heo, H. Kim, C.-O. Yi, H. J. Shin, J. W. Han, G. S. Roh, J. Neural Transm., 2014, doi:10.1007/s00702-014-1208-0.
38. R. E. Carlisle, E. Brimble, K. E. Werner, G. L. Cruz, K. Ask, A. J. Ingram, J. G. Dickhout, PLoS One, 2014, 9, 1.
39. C.-M. Liu, G. H. Zheng, Q. L. Ming, J. M. Sun, C. Cheng, Free Radical Res., 2013, 47, 192.
40. W. Zha, G. Liang, J. Xiao, E. J. Studer, P. B. Hylemon, W. M. Pandak, G. Wang, X. Li, H. Zhou, PLoS One, 2010, 5, e9069.
41. N. M. Sakhrani, H. Padh, Drug Des., Dev. Ther., 2013, 7, 585.
42. W. Paschen, Cell Calcium, 2003, 34, 365.
43. S. S. Cao, R. J. Kaufman, Expert Opin. Ther. Targets, 2013, 17, 437.