Hinnuliquinone, a C2-symmetric dimeric non-peptide fungal metabolite inhibitor of HIV-1 protease

Biochemical and Biophysical Research Communications

Volumn 324, Issue 1, 2004, Pages 108-113

  Singh, Sheo B ^a   Ondeyka, John G ^a   Tsipouras, Nasios ^a   Ruby, Carolyn ^a   Sardana, Vinod ^a   Schulman, Marvin ^a   Sanchez, Manuel ^b   Pelaez, Fernando ^b   Stahlhut, Mark W ^a   Munshi, Sanjeev ^a   Olsen, David B ^a   Lingham, Russell B ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

^b Medical affairs Merck sharp and Dohme ltd   (Spain)

Author keywords

Fungal metabolite; Hinnuliquinone; HIV 1 protease inhibitor; Inhibitor bound X ray structure of protease

Indexed keywords

HINNULIQUINONE; PROTEINASE INHIBITOR; QUINONE DERIVATIVE; UNCLASSIFIED DRUG; BENZOQUINONE DERIVATIVE; FUNGAL PROTEIN; INDOLE DERIVATIVE; NORASTERRIQUINONE B1; PROTEINASE;

ARTICLE; BIOASSAY; CONTROLLED STUDY; CRYSTALLOGRAPHY; DIMERIZATION; ENZYME ACTIVITY; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; PRIORITY JOURNAL; WILD TYPE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ENZYME ACTIVE SITE; ENZYMOLOGY; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; METABOLISM; MICROBIOLOGY; OAK;

HUMAN IMMUNODEFICIENCY VIRUS 1;

BENZOQUINONES; CATALYTIC DOMAIN; DIMERIZATION; FUNGAL PROTEINS; HIV INFECTIONS; HIV PROTEASE; HIV PROTEASE INHIBITORS; HIV-1; HUMANS; INDOLES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; QUERCUS; QUINONES;

EID: 4744348329     PISSN: 0006291X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbrc.2004.08.234     Document Type: Article

References (28)

1. D. Leung, G. Abbenante, and D.P. Fairlie Protease inhibitors: current status and future prospects J. Med. Chem. 43 2000 305 341
2. J. Ondeyka, O.D. Hensens, D. Zink, R. Ball, R.B. Lingham, G. Bills, A. Dombrowski, and M. Goetz L-696,474, a novel cytochalasin as an inhibitor of HIV-1 protease. II. Isolation and structure J. Antibiotics 45 1992 679 685
3. R.B. Lingham, A. Hsu, K.C. Silverman, G.F. Bills, A.W. Dombrowski, M.E. Goldman, P.L. Darke, L. Huang, G. Koch, J.G. Ondeyka, and M.A. Goetz L-696,474, A novel cytochalasin as an inhibitor of HIV-1 protease III. Biological activity J. Antibiotics 45 1992 686 691
4. D.B. Olsen, M.W. Stahlhut, C.A. Rutkowski, H.B. Schock, A.L. vanOlden, and L.C. Kuo Non-active site changes elicit broad-based cross-resistance of the HIV-1 protease to inhibitors J. Biol. Chem. 274 1999 23699 23701
5. G.M. Salituro, F. Pelaez, and B.B. Zhang Discovery of a small molecule insulin receptor activator Recent Prog. Horm. Res. 56 2001 107 126
6. J. Collado, G. Platas, I. Martin, and F. Peláez Geographical and seasonal influences on the distribution of fungal endophytes in Quercus ilex New Phytologist 144 1999 525 532
7. F. Peláez, J. Collado, F. Arenal, A. Basilio, M.A. Cabello, M.T. Díez, J.B. García, A. González del Val, V. González, J. Gorrochategui, P. Hernández, I. Martín, G. Platas, and F. Vicente Endophytic fungi from plants living on gypsum soils as a source of secondary metabolites with antimicrobial activity Mycol. Res. 102 1998 755 761
8. S.B. Singh, H. Jayasuriya, R. Dewey, J.D. Polishook, A.W. Dombrowski, D.L. Zink, Z. Guan, J. Collado, G. Platas, F. Peláez, P.J. Felock, and D.J. Hazuda Isolation, structure and HIV-1-integrase inhibitory activity of structurally diverse fungal metabolites J. Ind. Microbiol. Biotechnol. 30 2003 721 731
9. Z. Chen, Y. Li, E. Chen, D.L. Hall, P.L. Darke, C. Culberson, J.A. Shafer, and L.C. Kuo Crystal-structure at 1.9-angstrom resolution of human immunodeficiency virus (HIV)-II protease complexed with L-735,524, an orally bioavailable inhibitor of the HIV proteases J. Biol. Chem. 269 1994 26344 26348
10. S. Munshi, Z. Chen, Y. Li, D.B. Olsen, M.E. Fraley, R.W. Hungate, and L.C. Kuo Rapid X-ray diffraction analysis of HIV-1 protease-inhibitor complexes: inhibitor exchange in single crystals of the bound enzyme Acta Cryst. D 54 1998 1053 1060
11. Z. Otwinowski, and W. Minor Processing of X-ray diffraction data collected in oscillation mode Macromol. Cryst. A 276 1997 307 326
12. M.A. O'Leary, and J.R. Hansen Hinnuliquinone, a isindolyl-2,5- dihydpigment pigment from Nodulisporium hinnuleum Tetrahedron Lett. 23 1982 1855 1856
13. M.A. O'Leary, J.R. Hanson, and B.L. Yeoh The structure and biosynthesis of hinnuliquinone, a pigment from Nodulisporium hinnuleum J. Chem. Soc. Perkin Trans. 1 1984 567 569
14. A. Fredenhagen, F. Petersen, M. Tintelnot-Blomley, J. Rosel, H. Mett, and P. Hug Semicochliodinol A and B: inhibitors of HIV-1 protease and EGF-R protein tyrosine kinase related to asterriquinones produced by the fungus Chrysosporium merdarium J. Antibiotics 50 1997 395 401
15. W. Schaal, A. Karlsson, G. Ahlsen, J. Lindberg, H.O. Andersson, U.H. Danielson, B. Classon, T. Unge, B. Samuelsson, J. Hulten, A. Hallberg, and A. Karlen Synthesis and comparative molecular field analysis (CoMFa) of symmetric and nonsymmetric cyclic sulfamide HIV-1 protease inhibitors J. Med. Chem. 44 2001 155 169
16. B. Zhang, G. Salituro, D. Szalkowski, Z. Li, Y. Zhang, I. Royo, D. Vilella, M.T. Diez, F. Pelaez, C. Ruby, R.L. Kendall, X. Mao, P. Griffin, J. Calaycay, J.R. Zierath, J.V. Heck, R.G. Smith, and D.E. Moller Discovery of a small molecule insulin mimetic with antidiabetic activity in mice Science 284 1999 974 977
17. N. Wilkie, P.B. Wingrove, J.G. Bilsland, L. Young, S.J. Harper, F. Hefti, S. Ellis, and S.J. Pollack The non-peptidyl fungal metabolite L-783,281 activates TRK neurotrophin receptors J. Neurochem. 78 2001 1135 1145
18. E.L. Air, M.Z. Strowski, S.C. Benoit, S.L. Conarello, G.M. Salituro, X.-M. Guan, K. Liu, S.C. Woods, and B.B. Zhang Small molecule insulin mimetics reduce food intake and body weight and prevent development of obesity Nat. Med. 8 2002 179 183
19. M. Li, J.F. Youngren, V.P. Manchem, M. Kozlowski, B.B. Zhang, B.A. Maddux, and I.D. Goldfine Small molecule insulin receptor activators potentiate insulin action in insulin-resistant cells Diabetes 50 2001 2323 2328
20. K. Liu, L. Xu, D. Szalkowski, Z. Li, V. Ding, G. Kwei, S. Huskey, D.E. Moller, J.V. Heck, B.B. Zhang, and A.B. Jones Discovery of a potent, highly selective, and orally efficacious small-molecule activator of the insulin receptor J. Med. Chem. 43 2000 3487 3494
21. S.A. Qureshi, V. Ding, Z. Li, D. Szalkowski, D.E. Biazzo-Ashnault, D. Xie, R. Saperstein, E. Brady, S. Huskey, X. Shen, K. Liu, L. Xu, G.M. Salituro, J.V. Heck, D.E. Moller, A.B. Jones, and B.B. Zhang Activation of insulin signal transduction pathway and anti-diabetic activity of small molecule insulin receptor activators J. Biol. Chem. 275 2000 36590 36595
22. 2+] and insulin secretion from pancreatic beta-cells Diabetes 51 2002 S43 S49
23. B.E. Roggo, F. Petersen, R. Delmendo, H.B. Jenny, H.H. Peter, and J. Roesel 3-Alkanoyl-5-hydroxymethyl tetronic acid homologs and resistomycin: new inhibitors of HIV-1 protease. I. Fermentation, isolation and biological activity J. Antibiotics 47 1994 136 142
24. R. Kaneto, H. Chiba, K. Dobashi, I. Kojima, K. Sakai, N. Shibamoto, H. Nishida, R. Okamoto, H. Akagawa, and S. Mizuno Mer-N5075A, a potential HIV-1 protease inhibitor, produced by Streptomyces chromofuscus J. Antibiotics 46 1993 1622 1624
25. Y. Asami, T. Ogura, N. Otake, T. Nishimura, X. Yao, T. Sakurai, H. Nagasawa, S. Sakuda, and K. Tatsuta Isolation and synthesis of a new bioactive ellagic acid derivative from Combretum yunnanensis J. Nat. Prod. 66 2003 729 731
26. Z. Sui, R. Salto, J. Li, C. Craik, and P.R. Ortiz de Montellano Inhibition of the HIV-1 and HIV-2 proteases by curcumin and curcumin boron complexes Bioorg. Med. Chem. 1 1993 415 422
27. X.-W. Yang, J. Zhao, Y.-X. Cui, X.-H. Liu, C.-M. Ma, M. Hattori, and L.-H. Zhang Anti-HIV-1 protease triterpenoid saponins from the seeds of Aesculus chinensis J. Nat. Prod. 62 1999 1510 1513
28. B.C.M. Potts, D.J. Faulkner, J.A. Chan, G.C. Simolike, P. Offen, M.E. Hemling, and T.A. Francis Didemnaketals A and B, HIV-1 protease inhibitors from the ascidian Didemnum sp. J. Am. Chem. Soc. 113 1991 6321 6322