Natural product-inspired pyranonaphthoquinone inhibitors of indoleamine 2,3-dioxygenase-1 (IDO-1)*

Australian Journal of Chemistry

Volumn 66, Issue 1, 2013, Pages 40-49

  Bridewell, David J A ^a   Sperry, Jonathan ^b   Smith, Jason R ^c   Kosim Satyaputra, Priambudi ^c   Ching, Lai Ming ^a   Jamie, Joanne F ^c   Brimble, Margaret A ^b  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b UNIVERSITY OF AUCKLAND   (New Zealand)

^c MACQUARIE UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CELL VIABILITY; CELLULAR CONTEXTS; DRUG CONCENTRATION; NAPHTHOQUINONE; NATURAL PRODUCTS; PYRANONAPHTHOQUINONE; STRUCTURAL FEATURE;

ENZYME ACTIVITY; KETONES;

LEAD COMPOUNDS;

EID: 84872876505     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH12393     Document Type: Article

References (63)

1. K. Higuchi, S. Kuno, O. Hayaishi, Fed. Proc. 1963, 22, 243 (abstr
2. K. Higuchi, O. Hayaishi, Arch. Biochem. Biophys. 1967, 120, 397. doi:10.1016/0003-9861(67)90256-1
3. T. Shimizu, S. Nomiyama, F. Hirata, O. Hayaishi, J. Biol. Chem. 1978, 253, 4700
4. O. Takikawa, R. Yoshida, R. Kido, O. Hayaishi, J. Biol. Chem. 1986, 261, 3648
5. D.H. Munn, E. Shafizadeh, J.T. Attwood, I. Bondarev, A. Pashine, A.L. Mellor, J. Exp. Med. 1999, 189, 1363. doi:10.1084/JEM.189. 9.1363
6. D.H. Munn, M. Zhou, J.T. Attwood, Science 1998, 281, 1191. doi:10.1126/SCIENCE.281.5380.1191
7. G.J. Guillemin, B.J. Brew, C.E. Noonan, O. Takikawa, K.M. Cullen, Neuropathol. Appl. Neurobiol. 2005, 31, 395. doi:10.1111/J.1365-2990.2005.00655. X (Pubitemid 41059860)
8. T. Hayashi, L. Beck,C.Rossetto, X. Gong,O. Takikawa, K. Takabayashi, D.H. Broide, D.A. Carson, E. Raz, J. Clin. Invest. 2004, 114, 270
9. R. Potula, L. Poluektova, B. Knipe, J. Chrastil, D. Heilman, H. Dou, O. Takikawa, D.H. Munn, H.E. Gendelman, P. Persidsky, Blood 2005, 106, 2382. doi:10.1182/BLOOD-2005-04-1403 (Pubitemid 41510811)
10. O. Takikawa, R.J. Truscott, M. Fukao, S. Miwa, Adv. Exp. Med. Biol. 2003, 527, 277. doi:10.1007/978-1-4615-0135-0-31
11. M.C. Wichers, M.J. Maes, J. Psychiatry Neurosci. 2004, 29, 11
12. A.J. Muller, G.C. Prendergast, Cancer Res. 2005, 65, 8065. doi:10.1158/0008-5472.CAN-05-2213 (Pubitemid 41330565)
13. A.J. Muller, W.P. Malachowski, G.C. Prendergast, Expert Opin. Ther. Targets 2005, 9, 831. doi:10.1517/14728222.9.4.831 (Pubitemid 41131682)
14. Uyttenhove, L. Pilotte, I. Theate, V. Stroobant, D. Colau, N. Parmentier, T. Boon, B. van den Eynde, Nat. Med. 2003, 9, 1269. doi:10.1038/NM934 (Pubitemid 37279849)
15. J.B. Katz, A.J. Muller, G.C. Prendergast, Immunol. Rev. 2008, 222, 206. doi:10.1111/J.1600-065X.2008.00610.X (Pubitemid 351430372)
16. G.C. Prendergast, Oncogene 2008, 27, 3889. doi:10.1038/ONC.2008.35 (Pubitemid 351913639)
17. A.J. Muller, P.A. Scherle, Natl. Rev. 2006, 6, 613
18. A. Macchiarulo, E. Camiaoni, R. Nuti, R. Pellicciari, Amino Acids 2009, 37, 219. doi:10.1007/S00726-008-0137-3
19. X. Zheng, J. Koropatnick, M. Li, X. Zhang, F. Ling, X. Ren, X. Hao, H. Sun, C. Vladau, J.A. Franek, B. Feng, B.L. Urquhart, R. Zhong, D.J. Freeman, B. Garcia, W.P. Min, J. Immunol. 2006, 177, 5639
20. A.J. Muller, J.B. Duhadaway, P.S. Donover, E. Sutanto-Ward, G.C. Prendergast, Nat. Med. 2005, 11, 312. doi:10.1038/NM1196 (Pubitemid 40460560)
21. T. Banerjee, J.B. Duhadaway, P. Gaspari, E. Sutanto-Ward, D.H. Munn, A.L. Mellor, W.P. Malachowski, G.C. Prendergast, A.J. Muller, Oncogene 2008, 27, 2851. doi:10.1038/SJ.ONC.1210939 (Pubitemid 351620442)
22. S. Kumar, W.P. Malachowski, J.B. DuHadaway, J.M. LaLonde, P.J. Carroll, D. Jaller, R. Metz, G.C. Prendergast, A.J. Muller, J. Med. Chem. 2008, 51, 1706. doi:10.1021/JM7014155 (Pubitemid 351438852)
23. Y. Watanabe, F. Motokazu, H. Osamu, T. Tomio, U. Hamao, Biochem. Biophys. Res. Commun. 1978, 85, 273. doi:10.1016/S0006-291X(78) 80039-4
24. S.G. Cady, M. Sono, Arch. Biochem. Biophys. 1991, 291, 326. doi:10.1016/0003-9861(91)90142-6
25. M. Sono, S.G. Cady, Biochemistry 1989, 28, 5392. doi:10.1021/BI00439A012
26. N. Eguchi, Y. Watanabe, K. Kawanishi, Y. Hashimoto, O. Hayaishi, Arch. Biochem. Biophys. 1984, 232, 602. doi:10.1016/0003-9861(84) 90579-4
27. A.C. Peterson, A.J. La Loggia, L.K. Hamaker, R.A. Arend, P.L. Fisette, Y. Ozaki, J.A. Will, R.R. Brown, J.M. Cook, Med. Chem. Res. 1993, 7, 473
28. H. Sugimoto, S. Oda, T. Otsuki, T. Hino, T. Yoshida, Y. Shiro, Proc. Natl. Acad. Sci. USA 2006, 103, 2611. doi:10.1073/PNAS. 0508996103
29. S. Kumar, D. Jaller, B. Patel, J.M. LaLonde, J.B. DuHadaway, W.P. Malachowski, G.C. Prendergast, A.J. Muller, J. Med. Chem. 2008, 51, 4968. doi:10.1021/JM800512Z
30. H. Nakashima, Y. Uto, E. Nakata, H. Nagasawa, K. Ikkyu, N. Hiraoka, K. Nakashima, Y. Sasaki, H. Sugimoto, Y. Shiro, T. Hashimoto, Y. Okamoto, Y. Asakawa, H. Hori, Bioorg. Med. Chem. 2008, 16, 8661. doi:10.1016/J.BMC.2008.07. 087
31. H. Nakashima, K. Ikkyu, K. Nakashima, K. Sano, Y. Uto, E. Nakata, H. Nagasawa, H. Sugimoto, Y. Shiro, Y. Nakagawa, H. Hori, Adv. Exp. Med. Biol. 2010, 662, 415. doi:10.1007/978-1-4419-1241-1-60
32. E. Dolušić, P. Larrieu, S. Blanc, F. Sapunaric, B. Norberg, L. Moineaux, D. Colette, V. Stroobant, L. Pilotte, D. Colau, T. Ferain, G. Fraser, M. Galeni, J.-M. Frère, B. Masereel, B. van den Eynde, J. Wouters, R. Fre'de'rick, Bioorg. Med. Chem. 2011, 19, 1550. doi:10.1016/J.BMC. 2010.12.032
33. E. Dolušić, P. Larrieu, S. Blanc, F. Sapunaric, J. Pouyez, L. Moineaux, D. Colette, V. Stroobant, L. Pilotte, D. Colau, T. Ferain, G. Fraser, M. Galleni, J.-M. Frere, B. Masereel, B. van den Eynde, J. Wouters, R. Frederick, Eur. J. Med. Chem. 2011, 46, 3058. doi:10.1016/J.EJMECH.2011.02.049
34. K. Matsuno, K. Takai, Y. Isaka, Y. Unno, M. Sato, O. Takikawa, A. Asai, Bioorg. Med. Chem. Lett. 2010, 20, 5126. doi:10.1016/J.BMCL.2010.07.025
35. E.W. Yue, B. Douty, B. Wayland, M. Bower, X. Liu, L. Leffet, Q. Wang, K.J. Bowman, M.J. Hansbury, C. Liu, M. Wei, Y. Li, R. Wynn, T.C. Burn, H.K. Koblish, J.S. Fridman, B. Metcalf, P.A. Scherle, A.P. Combs, J. Med. Chem. 2009, 52, 7364. doi:10.1021/JM900518F
36. H.K. Koblish, M.J. Hansbury, K.J. Bowman, G. Yang, C.L. Neilan, P.J. Haley, T.C. Burn, P. Waeltz, R.B. Sparks, E.W. Yue, A.P. Combs, P.A. Scherle, K. Vaddi, J.S. Fridman, Mol. Cancer Ther. 2010, 9, 489. doi:10.1158/1535-7163.MCT- 09-0628
37. E. Vottero, A. Balgi, K. Woods, S. Tugendreich, T. Melese, R.J. Andersen, A.G. Mauk, M. Roberge, Biotechnol. J. 2006, 1, 282. doi:10.1002/BIOT.200600001
38. A.C. Terentis, M. Freewan, T.S. Sempertegui Plaza, M.J. Raftery, R. Stocker, S.R. Thomas, Biochemistry 2010, 49, 591. doi:10.1021/BI901546E
39. Q. Huang, M. Zheng, S. Yang, C. Kuang, C. Yu, Q. Yang, Eur. J. Med. Chem. 2011, 46, 5680. doi:10.1016/J.EJMECH.2011.08.044
40. F.U. Röhrig, S.R. Majjigapu, A. Grosdidier, S. Bron, V. Stroobant, L. Pilotte, D. Colau, P. Vogel, B.J. Van den Eynde, V. Zoete, O. Michielin, J. Med. Chem. 2012, 55, 5270. doi:10.1021/JM300260V
41. U.F. Röhrig, L. Awad, A. Grosdidier, P. Larrieu, V. Stroobant, D. Colau, V. Cerundolo, A.J. Simpson, P. Vogel, B.J. van den Eynde, V. Zoete, O. Michielin, J. Med. Chem. 2010, 53, 1172. doi:10.1021/JM9014718
42. S. John, S. Thangapandian, S. Sakkiah, K.W. Lee, Eur. J. Med. Chem. 2010, 45, 4004. doi:10.1016/J.EJMECH.2010.05.057
43. P. Gaspari, T. Banerjee, W.P. Malachowski, A.J. Muller, G.C. Prendergast, J. DuHadaway, S. Bennett, A.M. Donovan, J. Med. Chem. 2006, 49, 684. doi:10.1021/JM0508888 (Pubitemid 43157498)
44. H.C. Brastianos, E. Vottero, B.O. Patrick, R. Van Soest, T. Matainaho, A.G. Mauk, R.J. Andersen, J. Am. Chem. Soc. 2006, 128, 16046. doi:10.1021/JA067211
45. G. Carr, M.K. Chung, A.G. Mauk, R.J. Andersen, J. Med. Chem. 2008, 51, 2634. doi:10.1021/JM800143H (Pubitemid 351620784)
46. M. Volgraf, J.-P. Lumb, H.C. Brastianos, G. Carr, M.K.W. Chung, M. Muenzel, A.G. Mauk, R.J. Andersen, D. Trauner, Nat. Chem. Biol. 2008, 4, 535. doi:10.1038/NCHEMBIO.107
47. G. Carr, W. Tay, H. Bottriell, S.K. Andersen, G.A. Mauk, R.J. Andersen, Org. Lett. 2009, 11, 2996. doi:10.1021/OL900972J
48. A. Pereira, E. Vottero, M. Roberge, A.G. Mauk, R.J. Andersen, J. Nat. Prod. 2006, 69, 1496. doi:10.1021/NP060111X (Pubitemid 44899767)
49. E. Fahy, R.J. Andersen, C. Xu, J. Clardy, J. Org. Chem. 1986, 51, 5145. doi:10.1021/JO00376A017 (Pubitemid 17008563)
50. J. Sperry, P. Bachu, M.A. Brimble, Nat. Prod. Rep. 2008, 25, 376. doi:10.1039/B708811F (Pubitemid 351490295)
51. J. Sperry, I. Lorenzo-Castrillejo, M.A. Brimble, F. Machi'n, Bioorg. Med. Chem. 2009, 17, 7131. doi:10.1016/J.BMC.2009.08.064
52. K. Rathwell, J. Sperry, M.A. Brimble, Tetrahedron 2010, 66, 4002. doi:10.1016/J.TET.2010.04.048
53. J.S. Gibson, O. Andrey, M.A. Brimble, Synthesis 2007, 2611
54. P. Bachu, J. Sperry, M.A. Brimble, Tetrahedron 2008, 64, 4827. doi:10.1016/J.TET.2008.01.112
55. J. Sperry, J.J.P. Sejberg, F.M. Stiemke, M.A. Brimble, Org. Biomol. Chem. 2009, 7, 2599. doi:10.1039/B905077A
56. P. Bachu, J. Sperry, M.A. Brimble, Tetrahedron 2008, 64, 3343. doi:10.1016/J.TET.2008.01.135
57. M.A. Brimble, P. Bachu, J. Sperry, Synthesis 2007, 2887. doi:10.1055/S-2007-983848 (Pubitemid 47528871)
58. J. Sperry, J.S. Gibson, J.J.P. Sejberg, M.A. Brimble, Org. Biomol. Chem. 2008, 6, 4261. doi:10.1039/B813605J
59. C.J. Austin, J. Mizdrak, A. Matin, N. Sirijovski, P. Kosim-Satyaputra, R.D. Willows, T.H. Roberts, R.J. Truscott, G. Polekhina, M.W. Parker, J.F. Jamie, Protein Expr. Purif. 2004, 37, 392. doi:10.1016/J.PEP.2004.06.025 (Pubitemid 39187977)
60. D.J. Bridewell, G.J. Finlay, B.C. Baguley, Oncol. Res. 1997, 9, 535
61. D.J. Bridewell, A.C. Porter, G.J. Finlay, B.C. Baguley, Cancer Chemother. Pharmacol. 2008, 62, 753. doi:10.1007/S00280-007-0660-Z
62. I. Efimov, J. Basran, X. Sun, N. Chauhan, S.K. Chapman, C.G. Mowat, E.L. Raven, J. Am. Chem. Soc. 2012, 134, 3034. doi:10.1021/JA208694G
63. A. Haldane, K.M. Holdaway, G.J. Finlay, B.C. Baguley, Cancer Chemother. Pharmacol. 1993, 32, 463. doi:10.1007/BF00685891