A method for the rapid discovery of naturally occurring products by proteins immobilized on magnetic beads and reverse affinity chromatography

Chemistry - An Asian Journal

Volumn 4, Issue 12, 2009, Pages 1802-1808

  Arai, Midori A ^a   Kobatake, Eiji ^a   Koyano, Takashi ^b   Kowithayakorn, Thaworn ^c   Kato, Shigeaki ^d   Ishibashi, Masami ^a  

^a CHIBA UNIVERSITY   (Japan)

^b Temko Corporation   (Japan)

^c KHON KAEN UNIVERSITY   (Thailand)

^d UNIVERSITY OF TOKYO   (Japan)

Author keywords

Drug discovery; Liquid chromatography; Magnetic beads; Natural products; Proteins

Indexed keywords

DRUG DISCOVERY; MAGNETIC BEADS; NATURAL COMPOUNDS; NATURAL PRODUCTS; NATURALLY OCCURRING; SCREENING METHODS; TARGET COMPOUND; TARGET PROTEINS;

AFFINITY CHROMATOGRAPHY; CHROMATOGRAPHIC ANALYSIS; DRUG PRODUCTS; HIGH PRESSURE LIQUID CHROMATOGRAPHY; LIQUIDS; MAGNETISM; TARGETS;

PROTEINS;

BIOLOGICAL PRODUCT; IMMOBILIZED PROTEIN;

AFFINITY CHROMATOGRAPHY; ARTICLE; CHEMISTRY; ISOLATION AND PURIFICATION; MAGNETISM; METHODOLOGY;

BIOLOGICAL PRODUCTS; CHROMATOGRAPHY, AFFINITY; IMMOBILIZED PROTEINS; MAGNETICS;

EID: 73649100969     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200900357     Document Type: Article

References (32)

1. C. Hultschig, J. Kreutzberger, H. Seitz, Z. Konthur, K. Büssow, H. Lehrach, Curr. Opin. Chem. Biol. 2006, 10, 4-10;
2. Y. Fang, J. Lahiri, L. Picard, Drug Discovery Today 2003, 8, 755-761.
3. T. Kanayama, S. Mamiya, T. Nishihara, J. Nshikawa, J. Biochem. 2003, 133, 791-797;
4. M. Lepourcelet, Y. N. P. Chen, D. S. France, H. Wang, P. Crews, F. Peterson, C. Bruseo, A. W. Wood, R. A. Shivdasani, Cancer Cell 2004, 5, 91-102.
5. D. A. Annis, E. Nickbarg, X. Yang, M. R. Ziebell, C. E. Whitehurst, Curr. Opin. Chem. Biol. 2007, 11, 518-526.
6. Examples of finding natural products using immobilized proteins: a) β2-adrenoceptor on the surface of macro-pore silica: X. H. Zheng, X. F. Zhao, R. Yang, S. X. Wang, Y. M. Wei, and J. B. Zheng, Chin. Sci. Bull. 2008, 53, 842-847
7. polyclonal antibody used to mimic hepatitis C virus NS3 protease; polyclonal antibody immobilized column and MS technique: H. Luo, L. Chen, Z. Li, Z. Ding, and X. Xu, Anal. Chem. 2003, 75, 3994-3998
8. affinity chromatography with human serum albumin: H. Wang, H. Zou, J. Ni, L. Kong, S. Gao, and B. Guo, J. Chromatogr. A 2000, 870, 501-510.
9. Y.-w. Jun, J.-s. Choi, J. Cheon, Chem. Commun. 2007, 1203-1214.
10. I. S. Lee, N. Lee, J. Park, B. H. Kim, Y.-W. Yi, T. Kim, T. K. Kim, I. H. Lee, S. R. Paik, T. Hyeon, J. Am. Chem. Soc. 2006, 128, 10658-10659.
11. S. G. Grancharov, H. Zeng, S. Sun, S. X. Wang, S. O'Brien, C. B. Murray, J. R. Kirtley, G. A. Held, J. Phys. Chem. B 2005, 109, 13030-13035.
12. Y.-w. Jun, Y.-M. Huh, J.-s. Choi, J.-H. Lee, H.-T. Song, S. Kim, S. Yoon, K.-S. Kim, J.-S. Shin, J.-S. Suh, J. Cheon, J. Am. Chem. Soc. 2005, 127, 5732-5733.
13. K. Nishio, Y. Masaike, M. Ikeda, H. Narimatsu, N. Gokon, S. Tsubouchi, M. Hatakeyama, S. Sakamoto, N. Hanyu, A. Sandhu, H. Kawaguchi, M. Abe, H. Handa, Colloids Surf. B 2008, 64, 162-169.
14. Y. Kabe, H. Handa, Tanpakushitsu Kakusan Koso 2007, 52, 1637-1642.
15. R. H. Wasserman in VITAMIN D, 2nd ed. (Eds.: D. Feldman, J. W. Pike, F. H. Glorieux), Elsevier Academic Press, San Diego, 2005, pp. 412-451.
16. S. I. Harada, G. A. Rodan, Nature 2003, 423, 349-355
17. H. Yasuda, K. Higashio, T. Suda in VITAMIN D, 2nd ed. (Eds.: D. Feldman, J. W. Pike, F. H. Glorieux), Elsevier Academic Press, San Diego, 2005, pp. 665-685.
18. D. D. Bikle in VITAMIN D, 2nd ed. (Eds.: D. Feldman, J. W. Pike, F. H. Glorieux), Elsevier Academic Press, San Diego, 2005, pp. 609-630.
19. H. F. DeLuca, Am. J. Clin. Nutr. 2004, 80, 1689S-1696S;
20. J. P. T. M. van Leeuwen, H. A. P. Pols in VITAMIN D, 2nd ed. (Eds.: D. Feldman, J. W. Pike, F. H. Glorieux), Elsevier Academic Press, San Diego, 2005, pp. 1571-1597.
21. M. A. Arai, K.-i. Takeyama, S. Ito, S. Kato, T. C. Chen, A. Kittaka, Bioconjugate Chem. 2007, 18, 614-620.
22. For the binding affinity of 1 and 2 to VDR, see: R. Bouillon, W. H. Okamura, A.W. Norman, Endcrine Rev. 1995, 16, 200-257.
23. The structure of aglycone was determined by comparing reported 13C and 1H NMR spectroscopic data of labdane diterpene, 9-epi-and 4-epi-labdane diterpenes and their derivatives: a) J. A. Garbarino, A. Molinari, J. Nat. Prod. 1992, 55, 744-747
24. J. Kitajima, T. Komori, T. Kawasaki, Chem. Pharm. Bull. 1982, 30, 3912-3921;
25. A. F. Barrero, J. Altarejos, E. J. Alvarez-Manzaneda, J. M. Ramos, S. Salido, Tetrahedron 1993, 49, 6251-6262.
26. F. Bohlmann, J. Jakupovic, R. M. King, H. Robinson, Phytochemistry 1980, 19, 863-868;
27. T. Hieda, Y. Mikami, Y. Obi, T. Kisaki, Agric. Biol. Chem. 1982, 46, 2249-2255.
28. Representative 1H NMR peak pattern of α-or β- arabinofuranoside, see; R. R. Gadikota, C. S. Callam, B. J. Appelmelk, T. L. Lowary, J. Carbohydr. Chem. 2003, 22, 149-170.
29. R. D. Stipanovic, D. H. O'Brien, C. E. Rogers, T. E. Tompson, J. Agric. Food Chem. 1979, 27, 458-459.
30. S. Hara, H. Okabe, K. Mihashi, Chem. Pharm. Bull. 1987, 35, 501-506. The result of 4, see Supporting Information.
31. C. W. L. Bevan, D. E. U. Ekong, J. I. Okogun, J. Chem. Soc. C 1968, 1063-1066.
32. J. Du, M. L. Wang, R. Y. Chen, D. Q. Yu, Planta Med. 2001, 67, 542-547.