Selective inhibition of human type-5 17β-hydroxysteroid dehydrogenase (AKR1C3) by baccharin, a component of Brazilian propolis

Journal of Natural Products

Volumn 75, Issue 4, 2012, Pages 716-721

  Endo, Satoshi ^a   Matsunaga, Toshiyuki ^a   Kanamori, Ayano ^a   Otsuji, Yoko ^a   Nagai, Hiroko ^a   Sundaram, Krithika ^b   El Kabbani, Ossama ^b   Toyooka, Naoki ^c   Ohta, Shozo ^d   Hara, Akira ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^b MONASH UNIVERSITY   (Australia)

^c UNIVERSITY OF TOYAMA   (Japan)

^d Api Company Ltd   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

17 OXOSTEROID; ANTINEOPLASTIC AGENT; BACCHARIN; CINNAMIC ACID DERIVATIVE; METHIONINE; PHENYLALANINE; PROPOLIS; SERINE; TESTOSTERONE 17BETA DEHYDROGENASE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING SITE; CANCER CELL; CELL PROLIFERATION; CONTROLLED STUDY; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; MALE; MOLECULAR DOCKING; PROSTATE CANCER; PROTEIN EXPRESSION; SITE DIRECTED MUTAGENESIS; STEROID METABOLISM;

3-HYDROXYSTEROID DEHYDROGENASES; BRAZIL; CRYSTALLOGRAPHY, X-RAY; HUMANS; HYDROXYPROSTAGLANDIN DEHYDROGENASES; MALE; MOLECULAR CONFORMATION; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PROPOLIS; STEREOISOMERISM; TRICHOTHECENES;

EID: 84860321938     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np201002x     Document Type: Article

References (41)

1. Penning, T. M. Endocr. Rev. 1997, 18, 281-305
2. Penning, T. M. J. Steroid Biochem. Mol. Biol. 2011, 125, 46-56
3. Barski, O. A.; Tipparaju, S. M.; Bhatnagar, A. Drug Metab. Rev. 2008, 40, 553-624
4. Hoffmann, F.; Maser, E. Drug Metab. Rev. 2007, 39, 87-144
5. Penning, T. M.; Burczynski, M. E.; Jez, J. M.; Hung, C. F.; Lin, H. K.; Ma, H.; Moore, M.; Palackal, N.; Ratnam, K. Biochem. J. 2000, 351, 67-77
6. Vihko, P.; Herrala, A.; Härkönen, P.; Isomaa, V.; Kaija, H.; Kurkela, R.; Li, Y; Patrikainen, L.; Pulkka, A.; Soronen, P.; Törn, S. J. Steroid Biochem. Mol. Biol. 2005, 93, 277-283
7. Byrns, M. C.; Penning, T. M. Chem.-Biol. Interact. 2009, 178, 221-227
8. Penning, T. M. Curr. Opin. Endocrinol. Diabetes Obes. 2010, 17, 233-239
9. Guise, C. P.; Abbattista, M. R.; Singleton, R. S.; Holford, S. D.; Connolly, J.; Dachs, G. U.; Fox, S. B.; Pollock, R.; Harvey, J.; Guilford, P.; Doñate, F.; Wilson, W. R.; Patterson, A. V. Cancer Res. 2010, 70, 1573-1584
10. Downs, T. M.; Burton, D. W.; Araiza, F. L.; Hastings, R. H.; Deftos, L. J. Cancer Lett. 2011, 306, 52-59
11. Byrns, M. C.; Duan, L.; Lee, S. H.; Blair, I. A.; Penning, T. M. J. Steroid Biochem. Mol. Biol. 2010, 118, 177-187
12. Dozmorov, M. G.; Azzarello, J. T.; Wren, J. D.; Fung, K. M.; Yang, Q.; Davis, J. S.; Hurst, R. E.; Culkin, D. J.; Penning, T. M.; Lin, H. K. BMC Cancer 2010, 10, 672
13. Knudsen, K. E.; Penning, T. M. Trends Endocrinol. Metab. 2010, 21, 315-324
14. Byrns, M. C.; Jin, Y.; Penning, T. M. J. Steroid Biochem. Mol. Biol. 2011, 125, 95-104
15. Higaki, Y.; Usami, N.; Shintani, S.; Ishikura, S.; El-Kabbani, O.; Hara, A. Chem.-Biol. Interact. 2003, 143-144, 503-513
16. Qiu, W.; Zhou, M.; Mazumdar, M.; Azzi, A.; Ghanmi, D.; Luu-The, V.; Labrie, F.; Lin, S. X. J. Biol. Chem. 2007, 282, 8368-8379
17. Byrns, M. C.; Steckelbroeck, S.; Penning, T. M. Biochem. Pharmacol. 2008, 75, 484-493
18. Adeniji, A. O.; Twenter, B. M.; Byrns, M. C.; Jin, Y.; Winkler, J. D.; Penning, T. M. Bioorg. Med. Chem. Lett. 2011, 21, 1464-1468
19. Brožič, P.; Turk, S.; Rižner, T. L.; Gobec, S. Curr. Med. Chem. 2011, 18, 2554-2565
20. De, P.; Baltas, M.; Bedos-Belval, F. Curr. Med. Chem. 2011, 18, 1672-1703
21. Kimoto, T.; Arai, S.; Kohguchi, M.; Aga, M.; Nomura, Y.; Micallef, M. J.; Kurimoto, M.; Mito, K. Cancer Detect. Prev. 1998, 22, 506-515
22. Akao, Y.; Maruyama, H.; Matsumoto, K.; Ohguchi, K.; Nishizawa, K.; Sakamoto, T.; Araki, Y.; Mishima, S.; Nozawa, Y. Biol. Pharm. Bull. 2003, 26, 1057-1059
23. Mishima, S.; Ono, Y.; Araki, Y.; Akao, Y.; Nozawa, Y. Biol. Pharm. Bull. 2005, 28, 1025-1030
24. Shimizu, K.; Das, S. K.; Hashimoto, T.; Sowa, Y.; Yoshida, T.; Sakai, T.; Matsuura, Y.; Kanazawa, K. Mol. Carcinog. 2005, 44, 293-299
25. Messerli, S. M.; Ahn, M. R.; Kunimasa, K.; Yanagihara, M.; Tatefuji, T.; Hashimoto, K.; Mautner, V.; Uto, Y.; Hori, H.; Kumazawa, S.; Kaji, K.; Ohta, T.; Maruta, H. Phytother. Res. 2009, 23, 423-427
26. Izuta, H.; Narahara, Y.; Shimazawa, M.; Mishima, S.; Kondo, S.; Hara, H. Biol. Pharm. Bull. 2009, 32, 1947-1951
27. Brozic, P.; Golob, B.; Gomboc, N.; Rizner, T. L.; Gobec, S. Mol. Cell. Endocrinol. 2006, 248, 233-235
28. Endo, S.; Matsunaga, T.; Ohta, C.; Soda, M.; Kanamori, A.; Kitade, Y.; Ohno, S.; Tajima, K.; El-Kabbani, O.; Hara, A. Chem.-Biol. Interact. 2011, 191, 261-268
29. Lovering, A. L.; Ride, J. P.; Bunce, C. M.; Desmond, J. C.; Cummings, S. M.; White, S. A. Cancer Res. 2004, 64, 1802-1810
30. Davies, N. J.; Hayden, R. E.; Simpson, P. J.; Birtwistle, J.; Mayer, K.; Ride, J. P.; Bunce, C. M. Cancer Res. 2009, 69, 4769-4775
31. Palackal, N. T.; Lee, S. H.; Harvey, R. G.; Blair, I. A.; Penning, T. M. J. Biol. Chem. 2002, 277, 24799-24808
32. El-Kabbani, O.; Scammells, P. J.; Gosling, J.; Dhagat, U.; Endo, S.; Matsunaga, T.; Soda, M.; Hara, A. J. Med. Chem. 2009, 52, 3259-3264
33. Paulino, N.; Abreu, S. R.; Uto, Y.; Koyama, D.; Nagasawa, H.; Hori, H.; Dirsch, V. M.; Vollmar, A. M.; Scremin, A.; Bretz, W. A. Eur. J. Pharmacol. 2008, 587, 296-301
34. Matsuura, K.; Hara, A.; Deyashiki, Y.; Iwasa, H.; Kume, T.; Ishikura, S.; Shiraishi, H.; Katagiri, Y. Biochem. J. 1998, 336, 429-436
35. Shiraishi, H.; Ishikura, S.; Matsuura, K.; Deyashiki, Y.; Ninomiya, M.; Sakai, S.; Hara, A. Biochem. J. 1998, 334, 399-405
36. Matsuura, K.; Shiraishi, H.; Hara, A.; Sato, K.; Deyashiki, Y.; Ninomiya, M.; Sakai, S. J. Biochem. 1998, 124, 940-946
37. Endo, S.; Matsunaga, T.; Mamiya, H.; Ohta, C.; Soda, M.; Kitade, Y.; Tajima, K.; Zhao, H. T.; El-Kabbani, O.; Hara, A. Arch. Biochem. Biophys. 2009, 487, 1-9
38. Friesner, R. A.; Banks, J. L.; Murphy, R. B.; Halgren, T. A.; Klicic, J. J.; Mainz, D. T.; Repasky, M. P.; Knoll, E. H.; Shelley, M.; Perry, J. K.; Shaw, D. E.; Francis, P.; Shenkin, P. S. J. Med. Chem. 2004, 47, 1739-1749
39. Matsunaga, T.; Haga, M.; Watanabe, G.; Shinoda, Y.; Endo, S.; Kajiwara, Y.; Tanaka, H.; Inagaki, N.; El-Kabbani, O.; Hara, A. Cell Tissue Res. 2012, 347, 407-417
40. Usui, S.; Matsunaga, T.; Ukai, S.; Kiho, T. Biosci. Biotechnol. Biochem. 1997, 61, 1924-1925
41. Ishikura, S.; Usami, N.; Nakajima, S.; Kameyama, A.; Shiraishi, H.; Carbone, V.; El-Kabbani, O.; Hara, A. Biol. Pharm. Bull. 2004, 27, 1939-1945