The arginine mimicking beta-amino acid beta(3)hPhe(3-H(2)N-CH(2)) as S1 ligand in cyclotheonamide-based beta-tryptase inhibitors

Janke D, Sommerhoff CP, Schaschke N (2011)
Bioorganic & Medicinal Chemistry 19(23): 7236-7243.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
beta-Tryptase, a mast-cell specific serine protease with trypsin-like activity, has emerged in the last years as a promising novel therapeutic target in the field of allergic inflammation. Recently, we have developed a potent and selective beta-tryptase inhibitor based on the natural product cyclotheonamide E4 by implementing a basic P3 residue that addresses the determinants of the extended substrate specificity of beta-tryptase. To further improve the affinity/selectivity profile of this lead structure, we have now investigated beta-homo-3-aminomethylphenylalanine as S1 ligand. In contrast to the corresponding beta-homo amino acids derived from lysine or arginine, we demonstrate that this particular basic beta-homo amino acid is a privileged S1 ligand for the development of beta-tryptase inhibitors. Besides affinity, selectivity and reduced basicity, these novel cyclotheonamide E4 analogs show excellent stability in human plasma and serum. (C) 2011 Elsevier Ltd. All rights reserved.
Erscheinungsjahr
Zeitschriftentitel
Bioorganic & Medicinal Chemistry
Band
19
Zeitschriftennummer
23
Seite
7236-7243
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Janke D, Sommerhoff CP, Schaschke N. The arginine mimicking beta-amino acid beta(3)hPhe(3-H(2)N-CH(2)) as S1 ligand in cyclotheonamide-based beta-tryptase inhibitors. Bioorganic & Medicinal Chemistry. 2011;19(23):7236-7243.
Janke, D., Sommerhoff, C. P., & Schaschke, N. (2011). The arginine mimicking beta-amino acid beta(3)hPhe(3-H(2)N-CH(2)) as S1 ligand in cyclotheonamide-based beta-tryptase inhibitors. Bioorganic & Medicinal Chemistry, 19(23), 7236-7243. doi:10.1016/j.bmc.2011.09.050
Janke, D., Sommerhoff, C. P., and Schaschke, N. (2011). The arginine mimicking beta-amino acid beta(3)hPhe(3-H(2)N-CH(2)) as S1 ligand in cyclotheonamide-based beta-tryptase inhibitors. Bioorganic & Medicinal Chemistry 19, 7236-7243.
Janke, D., Sommerhoff, C.P., & Schaschke, N., 2011. The arginine mimicking beta-amino acid beta(3)hPhe(3-H(2)N-CH(2)) as S1 ligand in cyclotheonamide-based beta-tryptase inhibitors. Bioorganic & Medicinal Chemistry, 19(23), p 7236-7243.
D. Janke, C.P. Sommerhoff, and N. Schaschke, “The arginine mimicking beta-amino acid beta(3)hPhe(3-H(2)N-CH(2)) as S1 ligand in cyclotheonamide-based beta-tryptase inhibitors”, Bioorganic & Medicinal Chemistry, vol. 19, 2011, pp. 7236-7243.
Janke, D., Sommerhoff, C.P., Schaschke, N.: The arginine mimicking beta-amino acid beta(3)hPhe(3-H(2)N-CH(2)) as S1 ligand in cyclotheonamide-based beta-tryptase inhibitors. Bioorganic & Medicinal Chemistry. 19, 7236-7243 (2011).
Janke, Dennis, Sommerhoff, Christian P., and Schaschke, Norbert. “The arginine mimicking beta-amino acid beta(3)hPhe(3-H(2)N-CH(2)) as S1 ligand in cyclotheonamide-based beta-tryptase inhibitors”. Bioorganic & Medicinal Chemistry 19.23 (2011): 7236-7243.

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A new approach to inhibit human β-tryptase by protein surface binding of four-armed peptide ligands with two different sets of arms.
Jiang QQ, Bartsch L, Sicking W, Wich PR, Heider D, Hoffmann D, Schmuck C., Org Biomol Chem 11(10), 2013
PMID: 23358683

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