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Volumn 42, Issue 28, 2003, Pages 3251-3253

Molecular-size reduction of a potent CXCR4-chemokine antagonist using orthogonal combination of conformation- and sequence-based libraries

Author keywords

Antagonists; Antiviral agents; Drug design; High throughput screening; Peptides

Indexed keywords

CONFORMATIONS; LEAD COMPOUNDS;

EID: 10744227507     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351024     Document Type: Article
Times cited : (197)

References (21)
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    • Cyclic oligopeptides, which are relatively constrained by a ring structure, have been successfully employed for designing nonpeptidic agents in medicinal chemistry, see a) T. Fukami, T. Nagase, K. Fujita, T. Hayama, K. Niiyama, T. Mase, S. Nakajima, T. Fukuroda, T. Saeki, M. Nishikibe, M. Ihara, M. Yano, K. Ishikawa, J. Med. Chem. 1995, 38, 4309; b) R. Haubner, R. Gratias, B. Diefenbach, S. L. Goodman, A. Jonczyk, H. Kessler, J. Am. Chem. Soc. 1996, 118, 7461; c) A. F. Spatola, Y. Crozet, J. Med. Chem. 1996, 39, 3842; d) J. Wermuth, S. L. Goodman, A. Jonczyk, H. Kessler, J. Am. Chem. Soc. 1997, 119, 1328; e) R. Haubner, D. Finsinger, H. Kessler, Angew. Chem. 1997, 109, 1440; Angew. Chem. Int. Ed. Engl. 1997, 36, 1374; f) K. Nakayama, H. C. Kawano, H. Inagaki, T. Ohta, Org. Lett. 2001, 3, 3447; g) H. C. Kawano, K. Nakayama, H. Inagaki, T. Ohta, Org. Lett. 2001, 3, 3451.
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    • Cyclic oligopeptides, which are relatively constrained by a ring structure, have been successfully employed for designing nonpeptidic agents in medicinal chemistry, see a) T. Fukami, T. Nagase, K. Fujita, T. Hayama, K. Niiyama, T. Mase, S. Nakajima, T. Fukuroda, T. Saeki, M. Nishikibe, M. Ihara, M. Yano, K. Ishikawa, J. Med. Chem. 1995, 38, 4309; b) R. Haubner, R. Gratias, B. Diefenbach, S. L. Goodman, A. Jonczyk, H. Kessler, J. Am. Chem. Soc. 1996, 118, 7461; c) A. F. Spatola, Y. Crozet, J. Med. Chem. 1996, 39, 3842; d) J. Wermuth, S. L. Goodman, A. Jonczyk, H. Kessler, J. Am. Chem. Soc. 1997, 119, 1328; e) R. Haubner, D. Finsinger, H. Kessler, Angew. Chem. 1997, 109, 1440; Angew. Chem. Int. Ed. Engl. 1997, 36, 1374; f) K. Nakayama, H. C. Kawano, H. Inagaki, T. Ohta, Org. Lett. 2001, 3, 3447; g) H. C. Kawano, K. Nakayama, H. Inagaki, T. Ohta, Org. Lett. 2001, 3, 3451.
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    • Cyclic oligopeptides, which are relatively constrained by a ring structure, have been successfully employed for designing nonpeptidic agents in medicinal chemistry, see a) T. Fukami, T. Nagase, K. Fujita, T. Hayama, K. Niiyama, T. Mase, S. Nakajima, T. Fukuroda, T. Saeki, M. Nishikibe, M. Ihara, M. Yano, K. Ishikawa, J. Med. Chem. 1995, 38, 4309; b) R. Haubner, R. Gratias, B. Diefenbach, S. L. Goodman, A. Jonczyk, H. Kessler, J. Am. Chem. Soc. 1996, 118, 7461; c) A. F. Spatola, Y. Crozet, J. Med. Chem. 1996, 39, 3842; d) J. Wermuth, S. L. Goodman, A. Jonczyk, H. Kessler, J. Am. Chem. Soc. 1997, 119, 1328; e) R. Haubner, D. Finsinger, H. Kessler, Angew. Chem. 1997, 109, 1440; Angew. Chem. Int. Ed. Engl. 1997, 36, 1374; f) K. Nakayama, H. C. Kawano, H. Inagaki, T. Ohta, Org. Lett. 2001, 3, 3447; g) H. C. Kawano, K. Nakayama, H. Inagaki, T. Ohta, Org. Lett. 2001, 3, 3451.
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    • 0035512704 scopus 로고    scopus 로고
    • Cyclic oligopeptides, which are relatively constrained by a ring structure, have been successfully employed for designing nonpeptidic agents in medicinal chemistry, see a) T. Fukami, T. Nagase, K. Fujita, T. Hayama, K. Niiyama, T. Mase, S. Nakajima, T. Fukuroda, T. Saeki, M. Nishikibe, M. Ihara, M. Yano, K. Ishikawa, J. Med. Chem. 1995, 38, 4309; b) R. Haubner, R. Gratias, B. Diefenbach, S. L. Goodman, A. Jonczyk, H. Kessler, J. Am. Chem. Soc. 1996, 118, 7461; c) A. F. Spatola, Y. Crozet, J. Med. Chem. 1996, 39, 3842; d) J. Wermuth, S. L. Goodman, A. Jonczyk, H. Kessler, J. Am. Chem. Soc. 1997, 119, 1328; e) R. Haubner, D. Finsinger, H. Kessler, Angew. Chem. 1997, 109, 1440; Angew. Chem. Int. Ed. Engl. 1997, 36, 1374; f) K. Nakayama, H. C. Kawano, H. Inagaki, T. Ohta, Org. Lett. 2001, 3, 3447; g) H. C. Kawano, K. Nakayama, H. Inagaki, T. Ohta, Org. Lett. 2001, 3, 3451.
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  • 10
    • 0035512137 scopus 로고    scopus 로고
    • Cyclic oligopeptides, which are relatively constrained by a ring structure, have been successfully employed for designing nonpeptidic agents in medicinal chemistry, see a) T. Fukami, T. Nagase, K. Fujita, T. Hayama, K. Niiyama, T. Mase, S. Nakajima, T. Fukuroda, T. Saeki, M. Nishikibe, M. Ihara, M. Yano, K. Ishikawa, J. Med. Chem. 1995, 38, 4309; b) R. Haubner, R. Gratias, B. Diefenbach, S. L. Goodman, A. Jonczyk, H. Kessler, J. Am. Chem. Soc. 1996, 118, 7461; c) A. F. Spatola, Y. Crozet, J. Med. Chem. 1996, 39, 3842; d) J. Wermuth, S. L. Goodman, A. Jonczyk, H. Kessler, J. Am. Chem. Soc. 1997, 119, 1328; e) R. Haubner, D. Finsinger, H. Kessler, Angew. Chem. 1997, 109, 1440; Angew. Chem. Int. Ed. Engl. 1997, 36, 1374; f) K. Nakayama, H. C. Kawano, H. Inagaki, T. Ohta, Org. Lett. 2001, 3, 3447; g) H. C. Kawano, K. Nakayama, H. Inagaki, T. Ohta, Org. Lett. 2001, 3, 3451.
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    • Kawano, H.C.1    Nakayama, K.2    Inagaki, H.3    Ohta, T.4
  • 17
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    • note
    • An additional Gly residue was employed as a spacer to avoid epimerization of a C-terminal residue during cyclization in peptide synthesis.
  • 18
    • 0041488554 scopus 로고    scopus 로고
    • note
    • The synthesis and evaluation of cyclic peptides are described in detail in the Supporting Information.
  • 19
    • 0041488553 scopus 로고    scopus 로고
    • note
    • CXCR4 is known to participate in infection by X4-HIV virus,[9] and in our previous research the affinities of T140 derivatives for CXCR4 have correlated with the anti-HIV activity.


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