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Volumn 46, Issue 7, 2013, Pages 1567-1578

Chemical construction and structural permutation of potent cytotoxin polytheonamide B: Discovery of artificial peptides with distinct functions

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIN; PEPTIDOMIMETIC AGENT; POLYTHEONAMIDE B; PROTEIN;

EID: 84880277512     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar300315p     Document Type: Article
Times cited : (26)

References (45)
  • 1
    • 34247109045 scopus 로고    scopus 로고
    • Natural Products as Sources of New Drugs over the Last 25 Years
    • Newman, D. J.; Cragg, G. M. Natural Products as Sources of New Drugs over the Last 25 Years J. Nat. Prod. 2007, 70, 461-477
    • (2007) J. Nat. Prod. , vol.70 , pp. 461-477
    • Newman, D.J.1    Cragg, G.M.2
  • 2
    • 67650436176 scopus 로고    scopus 로고
    • Drug Discovery and Natural Products: End of an Era or an Endless Frontier?
    • Li, J. W.-H.; Vederas, J. C. Drug Discovery and Natural Products: End of an Era or an Endless Frontier? Science 2009, 325, 161-165
    • (2009) Science , vol.325 , pp. 161-165
    • Li, J.W.-H.1    Vederas, J.C.2
  • 3
    • 38949138457 scopus 로고    scopus 로고
    • Function-Oriented Synthesis, Step Economy, and Drug Design
    • Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Function-Oriented Synthesis, Step Economy, and Drug Design Acc. Chem. Res. 2008, 41, 40-49
    • (2008) Acc. Chem. Res. , vol.41 , pp. 40-49
    • Wender, P.A.1    Verma, V.A.2    Paxton, T.J.3    Pillow, T.H.4
  • 4
    • 78650111987 scopus 로고    scopus 로고
    • Probing the Biology of Natural Products: Molecular Editing by Diverted Total Synthesis
    • Szpilman, A. M.; Carreira, E. M. Probing the Biology of Natural Products: Molecular Editing by Diverted Total Synthesis Angew. Chem., Int. Ed. 2010, 49, 2-39
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 2-39
    • Szpilman, A.M.1    Carreira, E.M.2
  • 5
    • 77956034361 scopus 로고    scopus 로고
    • On the Reach of Chemical Science: Creation of a Mini-Pipline from an Academic Laboratory
    • Wilson, R. M.; Danishefsky, S. J. On the Reach of Chemical Science: Creation of a Mini-Pipline from an Academic Laboratory Angew. Chem., Int. Ed. 2010, 49, 6031-3056
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 6031-3056
    • Wilson, R.M.1    Danishefsky, S.J.2
  • 6
    • 14844362054 scopus 로고    scopus 로고
    • Molecular Mechanism Underlying Nonribosomal Peptide Synthesis: Approaches to New Antibiotics
    • Sieber, S. A.; Marahiel, M. A. Molecular Mechanism Underlying Nonribosomal Peptide Synthesis: Approaches to New Antibiotics Chem. Rev. 2005, 105, 715-738
    • (2005) Chem. Rev. , vol.105 , pp. 715-738
    • Sieber, S.A.1    Marahiel, M.A.2
  • 7
    • 67649604461 scopus 로고    scopus 로고
    • Ribosomal Peptide Natural Products: Bridging the Ribosomal and Nonribosomal Worlds
    • McIntosh, J. A.; Donia, M. S.; Schmidt, E. W. Ribosomal Peptide Natural Products: Bridging the Ribosomal and Nonribosomal Worlds Nat. Prod. Rep. 2009, 26, 537-559
    • (2009) Nat. Prod. Rep. , vol.26 , pp. 537-559
    • McIntosh, J.A.1    Donia, M.S.2    Schmidt, E.W.3
  • 8
    • 0028118767 scopus 로고
    • Polytheonamides, Unprecedented Highly Cytotoxic Polypeptides, from the Marine Sponge Theonella swinhoei: 1. Isolation and Component Amino Acids
    • Hamada, T.; Sugawara, T.; Matsunaga, S.; Fusetani, N. Polytheonamides, Unprecedented Highly Cytotoxic Polypeptides, from the Marine Sponge Theonella swinhoei: 1. Isolation and Component Amino Acids Tetrahedron Lett. 1994, 35, 719-720
    • (1994) Tetrahedron Lett. , vol.35 , pp. 719-720
    • Hamada, T.1    Sugawara, T.2    Matsunaga, S.3    Fusetani, N.4
  • 9
    • 11844280935 scopus 로고    scopus 로고
    • Polytheonamides A and B, Highly Cytotoxic, Linear Polypeptides with Unprecedented Structural Features, from the Marine Sponge Theonella swinhoei
    • Hamada, T.; Matsunaga, S.; Yano, G.; Fusetani, N. Polytheonamides A and B, Highly Cytotoxic, Linear Polypeptides with Unprecedented Structural Features, from the Marine Sponge Theonella swinhoei J. Am. Chem. Soc. 2005, 127, 110-118
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 110-118
    • Hamada, T.1    Matsunaga, S.2    Yano, G.3    Fusetani, N.4
  • 12
    • 81255152587 scopus 로고    scopus 로고
    • Dynamic Structure of the Polytheonamide B Channel Studied by Normal Mode Analysis
    • Mori, T.; Kokubo, H.; Oiki, S.; Okamoto, Y. Dynamic Structure of the Polytheonamide B Channel Studied by Normal Mode Analysis Mol. Simul. 2011, 37, 975-985
    • (2011) Mol. Simul. , vol.37 , pp. 975-985
    • Mori, T.1    Kokubo, H.2    Oiki, S.3    Okamoto, Y.4
  • 13
    • 0027360175 scopus 로고
    • High-Resolution Conformation of Gramicidin A in a Lipid-Bilayer by Solid-State NMR
    • Ketcham, R. R.; Hu, W.; Cross, T. A. High-Resolution Conformation of Gramicidin A in a Lipid-Bilayer by Solid-State NMR Science 1993, 261, 1457-1460
    • (1993) Science , vol.261 , pp. 1457-1460
    • Ketcham, R.R.1    Hu, W.2    Cross, T.A.3
  • 14
    • 0031830332 scopus 로고    scopus 로고
    • Recent Advances in the High Resolution Structures of Bacterial Channels: Gramicidin A
    • Wallace, B. A. Recent Advances in the High Resolution Structures of Bacterial Channels: Gramicidin A J. Struct. Biol. 1998, 121, 123-141
    • (1998) J. Struct. Biol. , vol.121 , pp. 123-141
    • Wallace, B.A.1
  • 16
    • 0030667666 scopus 로고    scopus 로고
    • A Channel-Forming Peptide Toxin: Polytheonamide from Marine Sponge (Theonella swinhoei)
    • Oiki, S.; Muramatsu, I.; Matsunaga, S.; Fusetani, N. A Channel-Forming Peptide Toxin: Polytheonamide from Marine Sponge (Theonella swinhoei) Folia Pharmacol. Jpn. 1997, 110 (Suppl. 1) 195-198
    • (1997) Folia Pharmacol. Jpn. , vol.110 , Issue.SUPPL. 1 , pp. 195-198
    • Oiki, S.1    Muramatsu, I.2    Matsunaga, S.3    Fusetani, N.4
  • 17
    • 77956921248 scopus 로고    scopus 로고
    • A Cytotoxic Peptide from a Marine Sponge Exhibits Ion Channel Activity through Vectorial-Insertion into the Membrane
    • Iwamoto, M.; Shimizu, H.; Muramatsu, I.; Oiki, S. A Cytotoxic Peptide from a Marine Sponge Exhibits Ion Channel Activity through Vectorial-Insertion into the Membrane FEBS Lett. 2010, 584, 3995-3999
    • (2010) FEBS Lett. , vol.584 , pp. 3995-3999
    • Iwamoto, M.1    Shimizu, H.2    Muramatsu, I.3    Oiki, S.4
  • 19
    • 79955785158 scopus 로고    scopus 로고
    • Functional Analysis of Synthetic Substructures of Polytheonamide B: A Transmembrane Channel-Forming Peptide
    • Matsuoka, S.; Shinohara, N.; Takahashi, T.; Iida, M.; Inoue, M. Functional Analysis of Synthetic Substructures of Polytheonamide B: A Transmembrane Channel-Forming Peptide Angew. Chem., Int. Ed. 2011, 50, 4879-4883
    • (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 4879-4883
    • Matsuoka, S.1    Shinohara, N.2    Takahashi, T.3    Iida, M.4    Inoue, M.5
  • 20
    • 80053571473 scopus 로고    scopus 로고
    • Total Synthesis and Functional Analysis of Non-Ribosomal Peptides
    • Inoue, M. Total Synthesis and Functional Analysis of Non-Ribosomal Peptides Chem. Rec. 2011, 11, 284-294
    • (2011) Chem. Rec. , vol.11 , pp. 284-294
    • Inoue, M.1
  • 21
    • 79953862276 scopus 로고    scopus 로고
    • Convergent Total Synthesis of the Complex Non-Ribosomal Peptide Polytheonamide B
    • Inoue, M.; Matsuoka, S. Convergent Total Synthesis of the Complex Non-Ribosomal Peptide Polytheonamide B Isr. J. Chem. 2011, 51, 346-358
    • (2011) Isr. J. Chem. , vol.51 , pp. 346-358
    • Inoue, M.1    Matsuoka, S.2
  • 22
    • 84866763630 scopus 로고    scopus 로고
    • Selective Modification of the N-Terminal Structure of Polytheonamide B Significantly Changes its Cytotoxicity and Activity as an Ion Channel
    • Shinohara, N.; Itoh, H.; Matsuoka, S.; Inoue, M. Selective Modification of the N-Terminal Structure of Polytheonamide B Significantly Changes its Cytotoxicity and Activity as an Ion Channel ChemMedChem 2012, 7, 1770-1773
    • (2012) ChemMedChem , vol.7 , pp. 1770-1773
    • Shinohara, N.1    Itoh, H.2    Matsuoka, S.3    Inoue, M.4
  • 23
    • 84865646614 scopus 로고    scopus 로고
    • Design, Synthesis and Functional Analysis of Dansylated Polytheonamide Mimic: An Artificial Peptide Ion Channel
    • Itoh, H.; Matsuoka, S.; Kreir, M.; Inoue, M. Design, Synthesis and Functional Analysis of Dansylated Polytheonamide Mimic: An Artificial Peptide Ion Channel J. Am. Chem. Soc. 2012, 134, 14011-14018
    • (2012) J. Am. Chem. Soc. , vol.134 , pp. 14011-14018
    • Itoh, H.1    Matsuoka, S.2    Kreir, M.3    Inoue, M.4
  • 24
    • 84872304749 scopus 로고    scopus 로고
    • Structural Permutation of Potent Cytotoxin, Polytheonamide B: Discovery of Cytotoxic Peptide with Altered Activity
    • Itoh, H.; Inoue, M. Structural Permutation of Potent Cytotoxin, Polytheonamide B: Discovery of Cytotoxic Peptide with Altered Activity ACS Med. Chem. Lett. 2013, 4, 52-56
    • (2013) ACS Med. Chem. Lett. , vol.4 , pp. 52-56
    • Itoh, H.1    Inoue, M.2
  • 25
    • 0007193238 scopus 로고    scopus 로고
    • Chemical Synthesis of Natural Product Peptides: Coupling Methods for the Incorporation of Noncoded Amino Acids into Peptides
    • Humphrey, J. M.; Chamberlin, A. R. Chemical Synthesis of Natural Product Peptides: Coupling Methods for the Incorporation of Noncoded Amino Acids into Peptides Chem. Rev. 1997, 97, 2243-2266
    • (1997) Chem. Rev. , vol.97 , pp. 2243-2266
    • Humphrey, J.M.1    Chamberlin, A.R.2
  • 27
    • 0023889559 scopus 로고
    • Chemical Synthesis of Peptides and Proteins
    • Kent, S. B. H. Chemical Synthesis of Peptides and Proteins Annu. Rev. Biochem. 1988, 57, 957-989
    • (1988) Annu. Rev. Biochem. , vol.57 , pp. 957-989
    • Kent, S.B.H.1
  • 29
    • 12044258245 scopus 로고
    • 1-Hydroxy-7-Azabenzotriazole. An Efficient Peptide Coupling Additive
    • Carpino, L. A. 1-Hydroxy-7-Azabenzotriazole. An Efficient Peptide Coupling Additive J. Am. Chem. Soc. 1993, 115, 4397-4398
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 4397-4398
    • Carpino, L.A.1
  • 30
    • 0033397158 scopus 로고    scopus 로고
    • Polypeptide Synthesis by the Thioester Method
    • Aimoto, S. Polypeptide Synthesis by the Thioester Method Biopolymers 1999, 51, 247-265
    • (1999) Biopolymers , vol.51 , pp. 247-265
    • Aimoto, S.1
  • 31
    • 77955656511 scopus 로고    scopus 로고
    • The Effect of Sulfur stereochemistry of l -β,β- Dimethylmethionine S -Oxide on the Physicochemical Properties of Truncated Polytheonamides
    • Matsuoka, S.; Mizoguchi, Y.; Itoh, H.; Okura, K.; Shinohara, N.; Inoue, M. The Effect of Sulfur stereochemistry of l -β,β-Dimethylmethionine S -Oxide on the Physicochemical Properties of Truncated Polytheonamides Tetrahadron Lett. 2010, 51, 4644-4647
    • (2010) Tetrahadron Lett. , vol.51 , pp. 4644-4647
    • Matsuoka, S.1    Mizoguchi, Y.2    Itoh, H.3    Okura, K.4    Shinohara, N.5    Inoue, M.6
  • 32
    • 0001427872 scopus 로고
    • Removal of the N-Terminal Residue of a Protein after Transamination
    • Dixon, H. B. F.; Moret, V. Removal of the N-Terminal Residue of a Protein after Transamination Biochem. J. 1965, 94, 463-469
    • (1965) Biochem. J. , vol.94 , pp. 463-469
    • Dixon, H.B.F.1    Moret, V.2
  • 33
    • 0030481087 scopus 로고    scopus 로고
    • Redox-Triggered Secondary Structure Changes in the Aggregated States of a Designed Methionine-Rich Peptide
    • Schenck, H. L.; Dado, G. P.; Gellman, S. H. Redox-Triggered Secondary Structure Changes in the Aggregated States of a Designed Methionine-Rich Peptide J. Am. Chem. Soc. 1996, 118, 12487-12494
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 12487-12494
    • Schenck, H.L.1    Dado, G.P.2    Gellman, S.H.3
  • 34
    • 0037449319 scopus 로고    scopus 로고
    • Activity of Single Ion Channel Proteins Detected with a Planar Microstructure
    • Fertig, N.; Klau, M.; George, M.; Blick, R. H.; Behrends, J. C. Activity of Single Ion Channel Proteins Detected with a Planar Microstructure Appl. Phys. Lett. 2002, 81, 4865-4867
    • (2002) Appl. Phys. Lett. , vol.81 , pp. 4865-4867
    • Fertig, N.1    Klau, M.2    George, M.3    Blick, R.H.4    Behrends, J.C.5
  • 36
    • 77249178764 scopus 로고    scopus 로고
    • Nanoscale Ionic Diodes with Tunable and Switchable Rectifying Behavior
    • Macrae, M. X.; Blake, S.; Mayer, M.; Yang, J. Nanoscale Ionic Diodes with Tunable and Switchable Rectifying Behavior J. Am. Chem. Soc. 2010, 132, 1766-1767
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 1766-1767
    • Macrae, M.X.1    Blake, S.2    Mayer, M.3    Yang, J.4
  • 37
    • 48849104292 scopus 로고    scopus 로고
    • A Voltage-Responding Ion Channel Derived by C-Terminal Modification of Gramicidin A
    • Reiß, P.; Al-Momani, L.; Koert, U. A Voltage-Responding Ion Channel Derived by C-Terminal Modification of Gramicidin A ChemBioChem 2008, 9, 377-379
    • (2008) ChemBioChem , vol.9 , pp. 377-379
    • Reiß, P.1    Al-Momani, L.2    Koert, U.3
  • 39
    • 0018694217 scopus 로고
    • A Double-Stranded β-Helix with Antiparallel Chains in a Crystalline Oligo- l - D -Peptide
    • Benedetti, E.; Di Blasio, B.; Pedone, C.; Lorenzi, G. P.; Tomasic, L.; Gramlich, V. A Double-Stranded β-Helix with Antiparallel Chains in a Crystalline Oligo- l-d -Peptide Nature 1979, 282, 630
    • (1979) Nature , vol.282 , pp. 630
    • Benedetti, E.1    Di Blasio, B.2    Pedone, C.3    Lorenzi, G.P.4    Tomasic, L.5    Gramlich, V.6
  • 40
    • 0031567125 scopus 로고    scopus 로고
    • Crystal Structure of the Gramicidin/Potassium Thiocyanate Complex
    • Doyle, D. A.; Wallace, B. A. Crystal Structure of the Gramicidin/Potassium Thiocyanate Complex J. Mol. Biol. 1997, 266, 963-977
    • (1997) J. Mol. Biol. , vol.266 , pp. 963-977
    • Doyle, D.A.1    Wallace, B.A.2
  • 41
    • 1242272756 scopus 로고    scopus 로고
    • Conformational and Structural Analysis of the Equilibrium between Single- and Double-Strand β-Helix of a d, l -Alternating Oligonorleucine
    • Navarro, E.; Fenude, E.; Celda, B. Conformational and Structural Analysis of the Equilibrium between Single- and Double-Strand β-Helix of a d, l -Alternating Oligonorleucine Biopolymers 2004, 73, 229-241
    • (2004) Biopolymers , vol.73 , pp. 229-241
    • Navarro, E.1    Fenude, E.2    Celda, B.3
  • 42
    • 14844296372 scopus 로고    scopus 로고
    • The Antiviral Antibiotic Feglymycin: First Direct-Methods Solution of a 1000+ Equal-Atom Structure
    • Bunkóczi, G.; Vértesy, L.; Sheldrick, G. M. The Antiviral Antibiotic Feglymycin: First Direct-Methods Solution of a 1000+ Equal-Atom Structure Angew. Chem., Int. Ed. 2005, 44, 1340-1342
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 1340-1342
    • Bunkóczi, G.1    Vértesy, L.2    Sheldrick, G.M.3
  • 43
    • 0348109450 scopus 로고    scopus 로고
    • The Growing Impact of Click Chemistry on Drug Discovery
    • Kolb, H. C.; Sharpless, K. B. The Growing Impact of Click Chemistry on Drug Discovery Drug Discovery Today 2003, 8, 1128-1137
    • (2003) Drug Discovery Today , vol.8 , pp. 1128-1137
    • Kolb, H.C.1    Sharpless, K.B.2
  • 44
    • 77953297817 scopus 로고    scopus 로고
    • Molecular Recognition at the Membrane-Water Interface: Controlling Integral Peptide Helices by Off-Membrance Nucleobase Pairing
    • For synthesis of 28-mer d, l -alternating peptide, see
    • For synthesis of 28-mer d, l -alternating peptide, see: Schneggenburger, P. E.; Müllar, S.; Worbs, B.; Steinem, C.; Diederichsen, U. Molecular Recognition at the Membrane-Water Interface: Controlling Integral Peptide Helices by Off-Membrance Nucleobase Pairing J. Am. Chem. Soc. 2010, 132, 8020-8028
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 8020-8028
    • Schneggenburger, P.E.1    Müllar, S.2    Worbs, B.3    Steinem, C.4    Diederichsen, U.5
  • 45
    • 0019883199 scopus 로고
    • Pyranine (8-Hydroxy-1,3,6-pyrenetrisulfonate) as a Probe of Internal Aqueous Hydrogen Ion Concentration in Phospholipid Vesicles
    • Clement, N. R.; Gould, J. M. Pyranine (8-Hydroxy-1,3,6- pyrenetrisulfonate) as a Probe of Internal Aqueous Hydrogen Ion Concentration in Phospholipid Vesicles Biochemistry 1981, 20, 1534-1538
    • (1981) Biochemistry , vol.20 , pp. 1534
    • Clement, N.R.1    Gould, J.M.2


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