Downsizing of an HIV-cell fusion inhibitor, T22 ([tyr5'12, lys7]- polyphemusin II), with the maintenance of anti-HIV activity and solution structure

Bioorganic and Medicinal Chemistry

Volumn 6, Issue 4, 1998, Pages 473-479

  Tamamura, Hirokazu ^a   Waki, Michinori ^b   Imai, Makoto ^a   Otaka, Akira ^a   Ibuka, Toshiro ^a   Waki, Koji ^b   Miyamoto, Kenji ^b   Matsumoto, Akiyoshi ^b   Murakami, Tsutomu ^c   Nakashima, Hideki ^d   Yamamoto, Naoki ^c   Fujii, Nobutaka ^a  

^a KYOTO UNIVERSITY   (Japan)

^b SEIKAGAKU CORPORATION   (Japan)

^c TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^d KAGOSHIMA UNIVERSITY   (Japan)

Author keywords

Anti HIV peptide; NMR; T22; Tachyplesin; TW70

Indexed keywords

ANTIRETROVIRUS AGENT; POLYPHEMUSIN II[5 TYROSINE 12 TYROSINE 7 LYSINE]; POLYPHEMUSIN II[DES(8 CYSTEINE 13 CYSTEINE 9 TYROSINE 12 TYROSINE)] [10 DEXTRO LYSINE 11 PROLINE]; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CIRCULAR DICHROISM; DISULFIDE BOND; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

AMINO ACID SEQUENCE; ANTI-HIV AGENTS; ANTIMICROBIAL CATIONIC PEPTIDES; CIRCULAR DICHROISM; DNA-BINDING PROTEINS; HIV-1; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR SEQUENCE DATA; PEPTIDES; PEPTIDES, CYCLIC; PROTEIN STRUCTURE, SECONDARY; SEQUENCE ALIGNMENT; STRUCTURE-ACTIVITY RELATIONSHIP;

HUMAN IMMUNODEFICIENCY VIRUS;

EID: 0032054508     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(97)10055-4     Document Type: Article

References (28)

1. A preliminary communication of a portion of this work has been presented: Waki, M.; Waki, K.; Miyamoto, K.; Matsumoto, A.; Tamamura, H.; Fujii, N.; Murakami, T.; Nakashima, H.; Yamamoto, N. Chem. Lett. 1996, 571.
2. (a) Nakamura, T.; Furunaka, H., Miyata, T.; Tokunaga, F.; Muta, T.; Iwanaga, S.; Niwa, M.; Takao, T.; Shimonishi, Y. J. Biol. Chem. 1988, 263, 16709.
3. (b) Miyata, T.; Tokunaga, F.; Yoneya, T.; Yoshikawa, K.; Iwanaga, S.; Niwa, M.; Takao, T.; Shimonishi, Y. J. Biochem. 1988, 106, 663.
4. (c) Muta, T.; Fujimoto, T.; Nakajima, H.; Iwanaga, S. J. Biochem. 1990, 108, 261.
5. t, tert-butyl; Pmc, 2,2,5,7,8-pentamethylchroman-6-sulfonyl; Trt, triphenylmethyl; MTT, 3′-(4, 5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide.
6. (a) Morimoto, M.; Mori, H.; Otake, T.; Ueba, N.; Kunita, N.; Niwa, M.; Murakami, T.; Iwanaga, S. Chemotherapy 1991, 37, 206.
7. (b) Murakami, T.; Niwa, M.; Tokunaga, F.; Miyata, T.; Iwanaga, S. Chemotherapy 1991, 37, 327.
8. (a) Masuda, M.; Nakashima, H.; Ueda, T.; Naba, H.; Ikoma, R.; Otaka, A.; Terakawa, Y.; Tamamura, H.; Ibuka, T.; Murakami, T.; Koyanagi, Y.; Waki, M.; Matsumoto, A.; Yamamoto, N.; Funakoshi, S.; Fujii, N. Biochem. Biophys. Res. Commun. 1992, 189, 845.
9. (b) Tamamura, H.; Murakami, T.; Masuda, M.; Otaka, A.; Takada, W.; Ibuka, T.; Nakashima, H.; Waki, M.; Matsumoto, A.; Yamamoto, N.; Fujii, N. Biochem. Biophys. Res. Commun. 1994, 205, 1729.
10. (c) Tamamura, H.; Otaka, A.; Takada, W.; Terakawa, Y.; Yoshizawa, H.; Masuda, M.; Ibuka, T.; Murakami, T.; Nakashima, H.; Waki, M.; Matsumoto, A.; Yamamoto, N.; Fujii, N. Chem. Pharm. Bull. 1995, 43, 12.
11. Tamamura, H.; Kuroda, M.; Masuda, M.; Otaka, A.; Funakoshi, S.; Nakashima, H.; Yamamoto, N.; Waki, M.; Matsumoto, A.; Lancelin, J. M.; Kohda, D.; Tate, S.; Inagaki, F.; Fujii, N. Biochim. Biophys. Acta 1993, 1163, 209.
12. Nakashima, H.; Masuda, M.; Murakami, T.; Koyanagi, Y.; Matsumoto, A.; Fujii, N.; Yamamoto, N. Antimicrob. Agents Chemother. 1992, 36, 1249.
13. (a) Weeks, B. S.; Nomizu, M.; Otaka, A.; Weston, C. A.; Okusu, A.; Tamamura, H.; Yamamoto, N.; Fujii, N. Biochem. Biophys. Res. Commun. 1995, 215, 626.
14. (b) Tamamura, H.; Ishihara, T.; Otaka, A.; Murakami, T.; Ibuka, T.; Waki, M.; Matsumoto, A.; Yamamoto, N.; Fujii, N. Biochim. Biophys. Acta 1996, 1298, 37.
15. Murakami, T.; Nakajima, T.; Koyanagi, Y.; Tachibana, K.; Fujii, N.; Tamamura, H.; Yoshida, N.; Waki, M.; Matsumoto, A.; Yoshie, O.; Kishimoto, T.; Yamamoto, N.; Nagasawa, T. J. Exp. Med. 1997, 186, 1389.
16. D'Souza, M. P.; Harden, V. A. Nature Medicine 1996, 2, 1293 (and references therein).
17. Wuthrich, K. in NMR of Proteins and Nucleic Acids; Wiley: New York, 1986.
18. Tamamura, H.; Ikoma, R.; Niwa, M.; Funakoshi, S.; Murakami, T.; Fujii, N. Chem. Pharm. Bull. 1993, 41, 978.
19. De Clercq, E. J. Med. Chem. 1995, 38, 2491.
20. Nakashima, H.; Kido, Y.; Kobayashi, N.; Motoki, Y.; Neushul, M.; Yamamoto, N. Antimicrob. Agents Chemother. 1986, 31, 1524.
21. Izumiya, N.; Kato, T.; Aoyagi, H.; Waki, M.; Kondo, M. in Synthetic Aspects of Biologically Active Cyclic Peptides - Gramicidin S and Tyrocidins, Kodansha: Tokyo, 1979.
22. Akaji, K.; Fujii, N.; Tokunaga, F.; Miyata, T.; Iwanaga, S.; Yajima, H. Chem. Pharm. Bull. 1989, 37, 2661.
23. Rink, H. Tetrahedron Lett. 1987, 28, 3787.
24. Fujii, N.; Otaka, A.; Sugiyama, N.; Hatano, M.; Yajima, H. Chem. Pharm. Bull. 1987, 35, 3880.
25. Piantini, U.; Sfrensen, O. W.; Ernst, R. R. J. Am. Chem. Soc. 1982, 104, 6800.
26. Bax, A.; Davis, D. G. J. Magn. Res. 1985, 65, 355.
27. Jeener, J.; Meier, M. H.; Bachmann, P.; Ernst, R. R. J. Chem. Phys. 1979, 71, 4546.
28. States, D. J.; Haberkorn, R. A.; Ruben, D. J. J. Magn. Res. 1982, 48, 286.