Celebesides A-C and theopapuamides B-D, depsipeptides from an indonesian sponge that inhibit HIV-1 entry

Journal of Organic Chemistry

Volumn 74, Issue 2, 2009, Pages 504-512

  Plaza, Alberto ^a   Bifulco, Giuseppe ^b   Keffer, Jessica L ^a   Lloyd, John R ^a   Baker, Heather L ^a   Bewley, Carole A ^a  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^b UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAMIDO; ACID MOIETIES; AMINO ACID RESIDUES; AMPHOTERICIN; ANTI-FUNGAL ACTIVITIES; CANDIDA ALBICANS; CYCLIC DEPSIPEPTIDES; DEPSIPEPTIDES; ESI-MS/MS; HUMAN COLONS; INFECTIVITY ASSAYS; MARINE SPONGES; N TERMINALS; POLYKETIDE; QUANTUM-MECHANICAL CALCULATIONS; RESISTANT STRAINS; STRUCTURAL CLASS; WILD TYPES;

AMINES; AMINO ACIDS; FATTY ACIDS; ORGANIC ACIDS; POLYMERS; POLYPEPTIDES; SUGAR (SUCROSE);

AMINATION;

AMPHOTERICIN B; CELEBESIDE A; CELEBESIDE B; CELEBESIDE C; CYCLODEPSIPEPTIDE; DEPSIPEPTIDE; FATTY ACID; HEXANOIC ACID DERIVATIVE; PHOSPHOSERINE; POLYKETIDE; PROPIONIC ACID DERIVATIVE; THEOPAPUAMIDE A; THEOPAPUAMIDE B; THEOPAPUAMIDE C; THEOPAPUAMIDE D; THREONINE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; THEOPAPUAMIDE;

AMINO TERMINAL SEQUENCE; ANTIFUNGAL ACTIVITY; ANTIFUNGAL RESISTANCE; ANTIVIRAL ACTIVITY; ARTICLE; CANCER CELL; CANDIDA ALBICANS; COLON CARCINOMA; CONCENTRATION RESPONSE; CYTOTOXICITY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 1 INFECTION; IC 50; INDONESIA; NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; SILIQUARIASPONGIA MIRABILIS; SPONGE (PORIFERA); STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY; VIRUS ENTRY; VIRUS INHIBITION; WILD TYPE; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG EFFECT; FUNGUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHYSIOLOGY; QUANTUM THEORY; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEPSIPEPTIDES; FUNGI; HIV-1; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PORIFERA; QUANTUM THEORY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; VIRUS INTERNALIZATION;

EID: 60849089353     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802232u     Document Type: Article

References (41)

1. Bewley, C. A.; Faulkner, D. J. Angew. Chem., Int. Ed. Engl. 1998, 37. 2162.
2. Matsunaga, S.; Fusetani, N. Curr. Org. Chem. 2003, 7, 945.
3. (a) Matsunaga, S.; Fusetani, N.; Kato, Y.; Hirota, H. J. Am. Chem. Soc. 1991, 113, 9690.
4. (b) Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Walchli, M. J. Am. Chem. Soc. 1989, 111, 2582.
5. (c) Bewley, C. A.; Faulkner, D. J. J. Org. Chem. 1994, 59, 4849.
6. (d) Youssef, D. T. A.; Mooberry, S. L. J. Nat. Prod. 2006, 69, 154.
7. (a) Kashman, Y.; Carmely, S. Tetrahedron Lett. 1985, 26, 511.
8. (b) Kobayashi, M.; Tanaka, J.; Katori, T.; Matsuura, M.; Kitagawa, I. Tetrahedron Lett. 1989, 22, 2963.
9. (c) Kitagawa, I.; Kobayashi, M.; Katori, T.; Yamashita, M.; Tanaka, J.; Doi, M.; Ishida, T. J. Am. Chem. Soc. 1990, 112, 3710.
10. (d) Doi, M.; Ishida, T.; Kobayashi, M.; Kitagawa, I. J. Org. Chem. 1991, 56, 3629.
11. (e) Hamada, T.; Matsunaga, S.; Yano, G.; Fusetani, N. J. Am. Chem. Soc. 2005, 127, 110.
12. (a) Sata, N. U.; Matsunaga, S.; Fusetani, N.; van Soest, R. W. M. J. Nat. Prod. 1999, 62, 969.
13. (b) Sata, N. U.; Wada, S.-i.; Matsunaga, S.; Watabe, S.; van Soest, R. W. M.; Fusetani, N. J. Org. Chem. 1999, 64, 2331.
14. Plaza, A.; Baker, H. L.; Bewley, C. A. J. Nat. Prod. 2008, 71, 473.
15. Plaza, A.; Gustchina, E.; Baker, H. L.; Kelly, M.; Bewley, C. A. J. Nat. Prod. 2007, 70, 1753.
16. Ratnayake, A. S.; Bugni, T. S.; Feng, X.; Harper, M. K.; Skalicky, J. J.; Mohammed, K. A.; Andjelic, C. D.; Barrows, L. R.; Ireland, C. M. J. Nat. Prod. 2006, 69, 1582.
17. (a) Fujii, K.; Ikai, Y.; Oka, H.; Suzuki, M.; Harada, K.-I. Anal. Chem. 1997, 69, 5146.
18. (b) Fujii, K.; Ikai, Y.; Mayumi, T.; Oka, H.; Suzuki, M.; Harada, K.-I. Anal. Chem. 1997, 69, 3346.
19. Bui, H. T. N.; Jansen, R.; Pham, H. T. L.; Mundt, S. J. Nat. Prod. 2007, 70, 499.
20. Goldberg, J.; Huang, H. B.; Kwon, Y. G.; Greengard, P.; Nairn, A. C.; Kuriyan, J. Nature 1995, 376, 745.
21. Matsumori, N.; Kaneno, D.; Murata, M.; Nakamura, H.; Tachibana, K. J. Org. Chem. 1999, 64, 866.
22. Griesinger, C.; Sorensen, O. W.; Ernst, R. R. J. Magn. Reson. 1987, 75, 474.
23. Uhrin, D.; Batta, G.; Hruby, V. J.; Barlow, P. N.; Koever, K. E. J. Magn. Reson. 1998, 130, 155.
24. (a) Marquez, B. L.; Gerwick, W. H.; Williamson, R. T. Magn. Reson.
25. Chem. 2001, 39, 499.
26. (b) Williamson, R. T.; Marquez, B. L.; Gerwick, W. H.; Kover, K. E. Magn. Reson. Chem. 2000, 38, 265.
27. Meissner, A.; Soerensen, O. W. Magn. Reson. Chem. 2001, 39, 49.
28. Bax, A.; Davis, D. G. J. Magn. Reson. 1985, 63, 207.
29. Bifulco, G.; Dambruoso, P.; Gomez-Paloma, L.; Riccio, R. Chem. Rev. 2007, 107, 3744.
30. Bifulco, G.; Bassarello, C.; Riccio, R.; Gomez-Paloma, L. Org. Lett. 2004, 6, 1025-1028.
31. Gaussian 03, Revision B.05: Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian, Inc., Wallingford, CT, 2004.
32. Okada, Y.; Matsunaga, S.; van Soest, R. W. M.; Fusetani, N. Org. Lett. 2002, 4, 3029.
33. (a) Shibazaki, M.; Sugawara, T.; Nagai, K.; Shimizu, Y.; Yamaguchi, H.; Suzuki, K. J. Antibiot. 1996, 49, 340.
34. (b) Sugawara, T.; Shibazaki, M.; Nakahara, H.; Suzuki, K. J. Antibiot. 1996, 49, 345.
35. Ermolenko, M. S. Tetrahedron Lett. 1996, 37, 6711.
36. Bax, A.; Freeman, R. J. Magn. Reson. 1981, 44, 542.
37. Zampella, A.; Sepe, V.; Luciano, P.; Bellotta, F.; Monti, M. C.; D'Auria, M. V.; Jepsen, T.; Petek, S.; Adeline, M.-T.; Laprevote, O.; Aubertin, A.-M.; Debitus, C.; Poupat, C.; Ahond, A. J. Org. Chem. 2008, 73, 5319.
38. Li, M.; Gao, F.; Mascola, J. R.; Stamatatos, L.; Polonis, V. R.; Koutsoukos, M.; Voss, G.; Goepfert, P.; Gilbert, P.; Greene, K. M.; Bilska, M.; Kothe, D. L.; Salazar-Gonzalez, J. F.; Wei, X.; Decker, J. M.; Hahn, B. H.; Montefiori, D. C. J. Virol. 2005, 79, 10108.
39. Gustchina, E.; Bewley, C. A.; Clore, G. M. J. Virol. 2008, in press; PMID 18667502.
40. Matsunaga, S.; Fusetani, N.; Kato, Y. J. Am. Chem. Soc. 1991, 113, 9690-9692.
41. Kobayashi, J.; Sato, M.; Ishibashi, M.; Shigemori, H.; Nakamura, T.; Ohizumi, Y. J. Chem. Soc., Perkin Trans. 1 1991, 1050-1052.