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Volumn 12, Issue 10, 2009, Pages 929-939

Cyclopeptide analogs for generating new molecular and 3D diversity

Author keywords

Cyclotetrapeptide; Peptide library; Retro inverso; Scaffold

Indexed keywords

CYCLOPEPTIDE; PEPTIDOMIMETIC AGENT;

EID: 71249158761     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/138620709789824754     Document Type: Article
Times cited : (8)

References (45)
  • 1
    • 33746879536 scopus 로고    scopus 로고
    • Peptides and peptidomimetics in medicine, surgery and biotechnology
    • Gentilucci, L.; Tolomelli, A.; Squassabia, F. Peptides and peptidomimetics in medicine, surgery and biotechnology. Curr. Med. Chem., 2006, 13(20), 2449-2466.
    • (2006) Curr. Med. Chem. , vol.13 , Issue.20 , pp. 2449-2466
    • Gentilucci, L.1    Tolomelli, A.2    Squassabia, F.3
  • 2
    • 0027626855 scopus 로고
    • Conformational and topographical considerations in the design of biologically active peptides
    • Hruby, V.J. Conformational and topographical considerations in the design of biologically active peptides. Biopolymers, 1993, 33(7), 1073-1082. (Pubitemid 23184442)
    • (1993) Biopolymers , vol.33 , Issue.7 , pp. 1073-1082
    • Hruby, V.J.1
  • 3
    • 0025336463 scopus 로고
    • Emerging approaches in the molecular design of receptor-selective peptide ligands: Conformational, topographical and dynamic considerations
    • Hruby, V.J.; Al-Obeidi, F.; Kazmierski, W. Emerging approaches in the molecular design of receptor-selective peptide ligands: conformational, topographical and dynamic considerations. Biochem. J., 1990, 268, 249-262. (Pubitemid 20193959)
    • (1990) Biochemical Journal , vol.268 , Issue.2 , pp. 249-262
    • Hruby, V.J.1    Al-Obeidi, F.2    Kazmierski, W.3
  • 5
    • 0038387389 scopus 로고    scopus 로고
    • A guide to drug discovery: Hit and lead generation: beyond high-throughput screening
    • Bleicher, K.H.; Boehm, H.-J.; Mueller, K.; Alanine, A.I. A guide to drug discovery: hit and lead generation: beyond high-throughput screening. Nat. Rev. Drug Discov., 2003, 2(5), 369-378.
    • (2003) Nat. Rev. Drug Discov. , vol.2 , Issue.5 , pp. 369-378
    • Bleicher, K.H.1    Boehm, H.-J.2    Mueller, K.3    Alanine, A.I.4
  • 6
    • 0037208308 scopus 로고    scopus 로고
    • Property distributions: Differences between drugs, natural products, and molecules from combinatorial chemistry
    • Feher, M.; Schmidt, J.M. Property distributions: differences between drugs, natural products, and molecules from combinatorial chemistry. J. Chem. Inf. Comput. Sci., 2003, 43(1), 218-227.
    • (2003) J. Chem. Inf. Comput. Sci. , vol.43 , Issue.1 , pp. 218-227
    • Feher, M.1    Schmidt, J.M.2
  • 7
    • 11144341956 scopus 로고    scopus 로고
    • Chemical space and biology
    • Dobson, C.M. Chemical space and biology. Nature, 2004, 432(7019), 824-828.
    • (2004) Nature , vol.432 , Issue.7019 , pp. 824-828
    • Dobson, C.M.1
  • 8
    • 0000734472 scopus 로고    scopus 로고
    • From chemical topology to 3D geometry
    • Balaban, A.T. From chemical topology to 3D geometry. J. Chem. Inf. Comput. Sci., 1997, 37(4), 645-650.
    • (1997) J. Chem. Inf. Comput. Sci. , vol.37 , Issue.4 , pp. 645-650
    • Balaban, A.T.1
  • 9
    • 17244370796 scopus 로고    scopus 로고
    • Over one hundred peptide-activated G protein-coupled receptors recognize ligands with turn structure
    • Tyndall, J.D.A.; Pfeiffer, B.; Abbenante, G.; Fairlie, D.P. Over one hundred peptide-activated G protein-coupled receptors recognize ligands with turn structure. Chem. Rev., 2005, 105(3), 793-826.
    • (2005) Chem. Rev. , vol.105 , Issue.3 , pp. 793-826
    • Tyndall, J.D.A.1    Pfeiffer, B.2    Abbenante, G.3    Fairlie, D.P.4
  • 10
    • 0033851469 scopus 로고    scopus 로고
    • Conformational and topographical considerations in designing agonist peptidomimetics from peptide leads
    • Hruby, V.J.; Balse, P.M. Conformational and topographical considerations in designing agonist peptidomimetics from peptide leads. Curr. Med. Chem., 2000, 7(9), 945-970.
    • (2000) Curr. Med. Chem. , vol.7 , Issue.9 , pp. 945-970
    • Hruby, V.J.1    Balse, P.M.2
  • 11
    • 33747478288 scopus 로고    scopus 로고
    • Conformation-activity relationship of designed glycopeptides as synthetic probes for the detection of autoantibodies, biomarkers of multiple sclerosis
    • DOI 10.1021/jm060117j
    • Carotenuto, A.; D'Ursi, A.M.; Mulinacci, B.; Paolini, I.; Lolli, F.; Papini, A.M.; Novellino, E.; Rovero, P. Conformation-activity relationship of designed glycopeptides as synthetic probes for the detection of autoantibodies, biomarkers of Multiple Sclerosis. J. Med. Chem., 2006, 49(17), 5072-5079. (Pubitemid 44260204)
    • (2006) Journal of Medicinal Chemistry , vol.49 , Issue.17 , pp. 5072-5079
    • Carotenuto, A.1    D'Ursi, A.M.2    Mulinacci, B.3    Paolini, I.4    Lolli, F.5    Papini, A.M.6    Novellino, E.7    Rovero, P.8
  • 12
    • 35948946972 scopus 로고    scopus 로고
    • A journey in structure-based drug discovery: From designed peptides to protein surface topomimetics as antibiotic and antiangiogenic agents
    • Dings, R.P.M.; Mayo, K.H. A journey in structure-based drug discovery: from designed peptides to protein surface topomimetics as antibiotic and antiangiogenic agents. Acc. Chem. Res., 2007, 40(10), 1057-1065.
    • (2007) Acc. Chem. Res. , vol.40 , Issue.10 , pp. 1057-1065
    • Dings, R.P.M.1    Mayo, K.H.2
  • 13
    • 33750709250 scopus 로고    scopus 로고
    • Syntheses of peptidomimetics based on pyranose and polyhydroxylated piperidine scaffolds
    • Murphy, P.V.; Dunne, J.L. Syntheses of peptidomimetics based on pyranose and polyhydroxylated piperidine scaffolds. Curr. Org. Synth., 2006, 3(4), 403-437.
    • (2006) Curr. Org. Synth. , vol.3 , Issue.4 , pp. 403-437
    • Murphy, P.V.1    Dunne, J.L.2
  • 15
    • 33344468779 scopus 로고    scopus 로고
    • Design, synthesis, and applications of 3-Aza-6, 8-Dioxabicyclo[3.2.1] Octane-based scaffolds for peptidomimetic chemistry
    • Trabocchi, A.; Menchi, G.; Guarna, F.; Machetti, F.; Scarpi, D.; Guarna, A. Design, synthesis, and applications of 3-Aza-6, 8-Dioxabicyclo[3.2.1]Octane- based scaffolds for peptidomimetic chemistry. Synlett, 2006, 3, 331-353.
    • (2006) Synlett , vol.3 , pp. 331-353
    • Trabocchi, A.1    Menchi, G.2    Guarna, F.3    Machetti, F.4    Scarpi, D.5    Guarna, A.6
  • 16
    • 0035959447 scopus 로고    scopus 로고
    • β-turn mimetic library synthesis: Scaffolds and applications
    • Souers, A.J.; Ellman, J.A. β-turn mimetic library synthesis: scaffolds and applications. Tetrahedron, 2001, 57(35), 7431-7448.
    • (2001) Tetrahedron , vol.57 , Issue.35 , pp. 7431-7448
    • Souers, A.J.1    Ellman, J.A.2
  • 17
    • 0037593636 scopus 로고    scopus 로고
    • Predicting the conformational states of cyclic tetrapeptides
    • DOI 10.1002/bip.10339
    • Loiseau, N.; Gomis, J.-M.; Santolini, J.; Delaforge, M.; Andre, F. Predicting the conformational states of cyclic tetrapeptides. Biopolymers, 2003, 69(3), 363-385. (Pubitemid 36841400)
    • (2003) Biopolymers , vol.69 , Issue.3 , pp. 363-385
    • Loiseau, N.1    Gomis, J.-M.2    Santolini, J.3    Delaforge, M.4    Andre, F.5
  • 18
    • 0034614056 scopus 로고    scopus 로고
    • Are β-amino acids γ-turn mimetics? Exploring a new design principle for bioactive cyclopeptides
    • Schumann, F.; Muller, A.; Koksch, M.; Muller, G.; Sewald, N. Are β-amino acids γ-turn mimetics? Exploring a new design principle for bioactive cyclopeptides. J. Am. Chem. Soc., 2000, 122(48), 12009-12010.
    • (2000) J. Am. Chem. Soc. , vol.122 , Issue.48 , pp. 12009-12010
    • Schumann, F.1    Muller, A.2    Koksch, M.3    Muller, G.4    Sewald, N.5
  • 19
    • 0037460144 scopus 로고    scopus 로고
    • Conformationally homogeneous cyclic tetrapeptides: Useful new three-dimensional scaffolds
    • Glenn, M.P.; Kelso, M.J.; Tyndall, J.D.A.; Fairlie, D.P. Conformationally homogeneous cyclic tetrapeptides: useful new three-dimensional scaffolds. J. Am. Chem. Soc., 2003, 125(3), 640-641.
    • (2003) J. Am. Chem. Soc. , vol.125 , Issue.3 , pp. 640-641
    • Glenn, M.P.1    Kelso, M.J.2    Tyndall, J.D.A.3    Fairlie, D.P.4
  • 21
    • 0000845126 scopus 로고
    • A dozen years of retro-inverso peptidomimetics
    • Chorev, M.; Goodman, M. A dozen years of retro-inverso peptidomimetics. Acc. Chem. Res., 1993, 26(5), 266-273.
    • (1993) Acc. Chem. Res. , vol.26 , Issue.5 , pp. 266-273
    • Chorev, M.1    Goodman, M.2
  • 22
    • 0011822184 scopus 로고    scopus 로고
    • Partially modified retro-inverso peptides: Development, synthesis, and conformational behavior
    • Fletcher, M.D.; Campbell, M.M. Partially modified retro-inverso peptides: development, synthesis, and conformational behavior. Chem. Rev., 1998, 98(2), 763-796.
    • (1998) Chem. Rev. , vol.98 , Issue.2 , pp. 763-796
    • Fletcher, M.D.1    Campbell, M.M.2
  • 23
    • 20344370972 scopus 로고    scopus 로고
    • The partial retro-inverso modification: A road traveled together
    • DOI 10.1002/bip.20219
    • Chorev, M. The partial retro-inverso modification: a road traveled together. Pept. Sci., 2005, 80(2-3), 67-84. (Pubitemid 40791045)
    • (2005) Biopolymers - Peptide Science Section , vol.80 , Issue.2-3 , pp. 67-84
    • Chorev, M.1
  • 24
    • 33846227460 scopus 로고    scopus 로고
    • Partial retro-inverso, retro, and inverso modifications of hydrazide linked bifunctional peptides for opioid and cholecystokinin (CCK) receptors
    • Lee, Y.S.; Agnes, R.S.; Davis, P.; Ma, S.-W.; Badghisi, H.; Lai, J.; Porreca, F.; Hruby, V.J. Partial retro-inverso, retro, and inverso modifications of hydrazide linked bifunctional peptides for opioid and cholecystokinin (CCK) receptors. J. Med. Chem., 2007, 50(1), 165-168.
    • (2007) J. Med. Chem. , vol.50 , Issue.1 , pp. 165-168
    • Lee, Y.S.1    Agnes, R.S.2    Davis, P.3    Ma, S.-W.4    Badghisi, H.5    Lai, J.6    Porreca, F.7    Hruby, V.J.8
  • 25
    • 33746163748 scopus 로고    scopus 로고
    • Olefin epoxidation catalysis by peptidic CoIIIcomplexes. Kor
    • Kim, K.-J.; Park, S.-W.; Yoon, S.S.J. Olefin epoxidation catalysis by peptidic Co(IIIcomplexes. Kor. Chem. Soc., 2000, 44(3), 286-289.
    • (2000) Chem. Soc. , vol.44 , Issue.3 , pp. 286-289
    • Kim, K.-J.1    Park, S.-W.2    Yoon, S.S.J.3
  • 26
    • 0037178340 scopus 로고    scopus 로고
    • 3-ethylene-bridged partially modified retro-inverso tetrapeptide β-turn mimetic: Design, synthesis, and structural characterizationt
    • DOI 10.1021/jo011041w
    • Han, Y.; Giragossian, C.; Mierke, D.F.; Chorev, M. Ni-to-Ni + 3-Ethylene-bridged partially modified retro-inverso tetrapeptide β-turn mimetic: design, synthesis, and structural characterization. J. Org. Chem., 2002, 67(15), 5085-5097. (Pubitemid 34793173)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.15 , pp. 5085-5097
    • Han, Y.1    Giragossian, C.2    Mierke, D.F.3    Chorev, M.4
  • 30
    • 0024287092 scopus 로고
    • The preparation of a partially protected heptasaccharide-asparagine intermediate for glycopeptide synthesis
    • Nakabayashi, S.; Warren, C.D.; Jeanloz, R.W. The preparation of a partially protected heptasaccharide-asparagine intermediate for glycopeptide synthesis. Carbohydr. Res., 1988, 174, 279-289.
    • (1988) Carbohydr. Res. , vol.174 , pp. 279-289
    • Nakabayashi, S.1    Warren, C.D.2    Jeanloz, R.W.3
  • 31
    • 37049089688 scopus 로고
    • Ring expansion of nitrogen-containing chloromethylheteroalicycles via aziridinium intermediates
    • Morie, T.; Kato, S.; Harada, H.; Fujiwara, I.; Watanabe, K.; Matsumoto, J.-I. Ring expansion of nitrogen-containing chloromethylheteroalicycles via aziridinium intermediates. J. Chem. Soc. Perkin Trans. 1. 1994, 18, 2565-2570.
    • (1994) J. Chem. Soc. Perkin Trans. , vol.1 , Issue.18 , pp. 2565-2570
    • Morie, T.1    Kato, S.2    Harada, H.3    Fujiwara, I.4    Watanabe, K.5    Matsumoto, J.-I.6
  • 32
    • 0032538362 scopus 로고    scopus 로고
    • The chemistry of vicinal diamines. Angew
    • Lucet, D.; Le Gall, T.; Mioskowski, C. The chemistry of vicinal diamines. Angew. Chem. Int. Ed. Engl., 1998, 37(19), 2580-12567
    • (1998) Chem. Int. Ed. Engl. , vol.37 , Issue.19 , pp. 2580-12567
    • Lucet, D.1    Le Gall, T.2    Mioskowski, C.3
  • 33
    • 0036411008 scopus 로고    scopus 로고
    • Selective synthesis of carbamate protected polyamines using alkyl phenyl carbonates
    • Pittelkow, M.; Lewinsky, R.; Christensen, J.B. Selective synthesis of carbamate protected polyamines using alkyl phenyl carbonates. Synthesis, 2002, 15, 2195-2202.
    • (2002) Synthesis , vol.15 , pp. 2195-2202
    • Pittelkow, M.1    Lewinsky, R.2    Christensen, J.B.3
  • 36
    • 2142823653 scopus 로고    scopus 로고
    • Recent advances in the investigation of the bioactive conformation of peptides active at the m-opioid receptor. Conformational analysis of endomorphins
    • DOI 10.2174/1568026043451627
    • Gentilucci, L.; Tolomelli, A. Recent advances in the investigation of the bioactive conformation of peptides active at the m-opioid receptor. Conformational analysis of endomorphins. Curr. Top. Med. Chem., 2004, 4(1), 105-121. (Pubitemid 38842562)
    • (2004) Current Topics in Medicinal Chemistry , vol.4 , Issue.1 , pp. 105-121
    • Gentilucci, L.1    Tolomelli, A.2
  • 37
    • 0025156939 scopus 로고
    • Cyclic pentapeptides as models for reverse turns: Determination of the equilibrium distribution between type I and type II conformations of Pro-Asn and Pro-Ala b-turns
    • Stradley, S.J.; Rizo, J.; Bruch, M.D.; Stroup, A.N.; Gierasch, L.M. Cyclic pentapeptides as models for reverse turns: Determination of the equilibrium distribution between type I and type II conformations of Pro-Asn and Pro-Ala b-turns. Biopolymers, 1990, 29(1), 263-287.
    • (1990) Biopolymers , vol.29 , Issue.1 , pp. 263-287
    • Stradley, S.J.1    Rizo, J.2    Bruch, M.D.3    Stroup, A.N.4    Gierasch, L.M.5
  • 38
    • 0020163940 scopus 로고
    • Conformation and biological activity of cyclic peptides
    • Kessler, H. Conformation and biological activity of cyclic peptides. Angew. Chem. Int. Ed. Engl., 1982, 21(7), 512-523.
    • (1982) Angew. Chem. Int. Ed. Engl. , vol.21 , Issue.7 , pp. 512-523
    • Kessler, H.1
  • 39
    • 0019267144 scopus 로고
    • Intramolecularly hydrogen-bonded peptide conformations
    • Toniolo, C. Intramolecularly hydrogen-bonded peptide conformations. CRC Crit. Rev. Biochem., 1980, 9(1), 1-44.
    • (1980) CRC Crit. Rev. Biochem. , vol.9 , Issue.1 , pp. 1-44
    • Toniolo, C.1
  • 40
    • 4744353375 scopus 로고    scopus 로고
    • Synthesis and evaluation of the affinity toward m-opioid receptors of atypical, lipophilic ligands based on the sequence c[-Tyr-Pro-Trp-Phe-Gly-]
    • DOI 10.1021/jm0498811
    • Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Spinosa, R.; Calienni, M.; Qasem, A.R.; Spampinato, S. Synthesis and evaluation of the affinity toward μioid receptors of atypical, lipophilic ligands based on the sequence c[-Tyr-Pro-Trp-Phe-Gly-]. J. Med. Chem., 2004, 47(21), 5198-5203. (Pubitemid 39314916)
    • (2004) Journal of Medicinal Chemistry , vol.47 , Issue.21 , pp. 5198-5203
    • Cardillo, G.1    Gentilucci, L.2    Tolomelli, A.3    Spinosa, R.4    Calienni, M.5    Qasem, A.R.6    Spampinato, S.7
  • 41
    • 33846004812 scopus 로고    scopus 로고
    • Re-discussion of the importance of ionic interactions in stabilizing ligand-opioid receptor complex and in activating signal transduction
    • DOI 10.2174/138945007779315704
    • Gentilucci, L.; Squassabia, F.; Artali, R. Re-discussion of the importance of ionic interactions in stabilizing ligand-opioid receptor complex and in activating signal transduction. Curr. Drug Targets, 2007, 8(1), 185-196. (Pubitemid 46043907)
    • (2007) Current Drug Targets , vol.8 , Issue.1 , pp. 185-196
    • Gentilucci, L.1    Squassabia, F.2    Artali, R.3
  • 44
    • 0041997867 scopus 로고    scopus 로고
    • Vitronectin receptor -avb3 integrin- Antagonists: Chemical and structural requirements for activity and selectivity
    • Henry, C.; Moitessier, N.; Chapleur, Y. Vitronectin receptor -avb3 integrin- antagonists: chemical and structural requirements for activity and selectivity. Mini. Rev. Med. Chem., 2002, 2(6), 531-542.
    • (2002) Mini. Rev. Med. Chem. , vol.2 , Issue.6 , pp. 531-542
    • Henry, C.1    Moitessier, N.2    Chapleur, Y.3


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