메뉴 건너뛰기




Volumn 27, Issue 12, 2016, Pages 2854-2862

Engineering an Affinity-Enhanced Peptide through Optimization of Cyclization Chemistry

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; AMINO ACIDS; BINDING ENERGY; COPPER COMPOUNDS; COVALENT BONDS; CYCLIZATION; CYCLOADDITION; DISSOCIATION; MACROPHAGES; SULFUR COMPOUNDS;

EID: 85006875514     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/acs.bioconjchem.6b00502     Document Type: Article
Times cited : (22)

References (36)
  • 1
    • 17844389346 scopus 로고    scopus 로고
    • Bioactive Peptides from Libraries
    • Falciani, C., Lozzi, L., Pini, A., and Bracci, L. (2005) Bioactive Peptides from Libraries Chem. Biol. 12, 417-426 10.1016/j.chembiol.2005.02.009
    • (2005) Chem. Biol. , vol.12 , pp. 417-426
    • Falciani, C.1    Lozzi, L.2    Pini, A.3    Bracci, L.4
  • 2
    • 79952662638 scopus 로고    scopus 로고
    • Computational approaches to therapeutic peptide discovery
    • Kliger, Y. (2010) Computational approaches to therapeutic peptide discovery Biopolymers 94, 701-710 10.1002/bip.21458
    • (2010) Biopolymers , vol.94 , pp. 701-710
    • Kliger, Y.1
  • 3
    • 84859483195 scopus 로고    scopus 로고
    • Peptides in cancer nanomedicine: Drug carriers, targeting ligands and protease substrates
    • Zhang, X.-X., Eden, H. S., and Chen, X. (2012) Peptides in cancer nanomedicine: drug carriers, targeting ligands and protease substrates J. Controlled Release 159, 2-13 10.1016/j.jconrel.2011.10.023
    • (2012) J. Controlled Release , vol.159 , pp. 2-13
    • Zhang, X.-X.1    Eden, H.S.2    Chen, X.3
  • 5
    • 0034734973 scopus 로고    scopus 로고
    • The use of phage display for the development of tumour targeting agents
    • Nilsson, F., Tarli, L., Viti, F., and Neri, D. (2000) The use of phage display for the development of tumour targeting agents Adv. Drug Delivery Rev. 43, 165-196 10.1016/S0169-409X(00)00068-5
    • (2000) Adv. Drug Delivery Rev. , vol.43 , pp. 165-196
    • Nilsson, F.1    Tarli, L.2    Viti, F.3    Neri, D.4
  • 6
    • 77950205585 scopus 로고    scopus 로고
    • Peptidic tumor targeting agents: The road from phage display peptide selections to clinical applications
    • Brown, K. C. (2010) Peptidic tumor targeting agents: the road from phage display peptide selections to clinical applications Curr. Pharm. Des. 16, 1040-1054 10.2174/138161210790963788
    • (2010) Curr. Pharm. Des. , vol.16 , pp. 1040-1054
    • Brown, K.C.1
  • 7
    • 84934441854 scopus 로고    scopus 로고
    • Peptide optimization and conjugation strategies in the development of molecularly targeted magnetic resonance imaging contrast agents
    • Kolodziej, A. F., Zhang, Z., Overoye-Chan, K., Jacques, V., and Caravan, P. (2014) Peptide optimization and conjugation strategies in the development of molecularly targeted magnetic resonance imaging contrast agents Methods Mol. Biol. 1088, 185-211 10.1007/978-1-62703-673-3-13
    • (2014) Methods Mol. Biol. , vol.1088 , pp. 185-211
    • Kolodziej, A.F.1    Zhang, Z.2    Overoye-Chan, K.3    Jacques, V.4    Caravan, P.5
  • 8
    • 46449115491 scopus 로고    scopus 로고
    • Hydrophile scanning as a complement to alanine scanning for exploring and manipulating protein-protein recognition: Application to the Bim BH3 domain
    • Boersma, M. D., Sadowsky, J. D., Tomita, Y. A., and Gellman, S. H. (2008) Hydrophile scanning as a complement to alanine scanning for exploring and manipulating protein-protein recognition: application to the Bim BH3 domain Protein Sci. 17, 1232-1240 10.1110/ps.032896.107
    • (2008) Protein Sci. , vol.17 , pp. 1232-1240
    • Boersma, M.D.1    Sadowsky, J.D.2    Tomita, Y.A.3    Gellman, S.H.4
  • 11
    • 84922041529 scopus 로고    scopus 로고
    • Maleimide-based method for elaboration of cysteine-containing peptide phage libraries
    • Santoso, B. and Murray, B. W. (2015) Maleimide-based method for elaboration of cysteine-containing peptide phage libraries Methods Mol. Biol. 1248, 267-276 10.1007/978-1-4939-2020-4-18
    • (2015) Methods Mol. Biol. , vol.1248 , pp. 267-276
    • Santoso, B.1    Murray, B.W.2
  • 12
    • 84880639988 scopus 로고    scopus 로고
    • Improving binding affinity and stability of peptide ligands by substituting glycines with D-amino acids
    • Chen, S., Gfeller, D., Buth, S. A., Michielin, O., Leiman, P. G., and Heinis, C. (2013) Improving binding affinity and stability of peptide ligands by substituting glycines with D-amino acids ChemBioChem 14, 1316-1322 10.1002/cbic.201300228
    • (2013) ChemBioChem , vol.14 , pp. 1316-1322
    • Chen, S.1    Gfeller, D.2    Buth, S.A.3    Michielin, O.4    Leiman, P.G.5    Heinis, C.6
  • 13
    • 84882267150 scopus 로고    scopus 로고
    • 1,2,3-Triazoles as amide bond mimics: Triazole scan yields protease-resistant peptidomimetics for tumor targeting
    • Valverde, I. E., Bauman, A., Kluba, C. A., Vomstein, S., Walter, M. A., and Mindt, T. L. (2013) 1,2,3-Triazoles as amide bond mimics: triazole scan yields protease-resistant peptidomimetics for tumor targeting Angew. Chem., Int. Ed. 52, 8957-8960 10.1002/anie.201303108
    • (2013) Angew. Chem., Int. Ed. , vol.52 , pp. 8957-8960
    • Valverde, I.E.1    Bauman, A.2    Kluba, C.A.3    Vomstein, S.4    Walter, M.A.5    Mindt, T.L.6
  • 16
    • 84969506943 scopus 로고    scopus 로고
    • Recent Advances Toward the Discovery of Drug-Like Peptides de novo
    • Goldflam, M. and Ullman, C. G. (2015) Recent Advances Toward the Discovery of Drug-Like Peptides De novo Front. Chem. 3, 69 10.3389/fchem.2015.00069
    • (2015) Front. Chem. , vol.3 , pp. 69
    • Goldflam, M.1    Ullman, C.G.2
  • 17
    • 84901681947 scopus 로고    scopus 로고
    • Hydrocarbon-Stapled Peptides: Principles, Practice, and Progress
    • Walensky, L. D. and Bird, G. H. (2014) Hydrocarbon-Stapled Peptides: Principles, Practice, and Progress J. Med. Chem. 57, 6275-6288 10.1021/jm4011675
    • (2014) J. Med. Chem. , vol.57 , pp. 6275-6288
    • Walensky, L.D.1    Bird, G.H.2
  • 18
    • 79959580534 scopus 로고    scopus 로고
    • Contemporary strategies for peptide macrocyclization
    • White, C. J. and Yudin, A. K. (2011) Contemporary strategies for peptide macrocyclization Nat. Chem. 3, 509-524 10.1038/nchem.1062
    • (2011) Nat. Chem. , vol.3 , pp. 509-524
    • White, C.J.1    Yudin, A.K.2
  • 19
    • 84916912015 scopus 로고    scopus 로고
    • Peptide stapling techniques based on different macrocyclisation chemistries
    • Lau, Y. H., de Andrade, P., Wu, Y., and Spring, D. R. (2015) Peptide stapling techniques based on different macrocyclisation chemistries Chem. Soc. Rev. 44, 91-102 10.1039/C4CS00246F
    • (2015) Chem. Soc. Rev. , vol.44 , pp. 91-102
    • Lau, Y.H.1    De Andrade, P.2    Wu, Y.3    Spring, D.R.4
  • 20
    • 73549100208 scopus 로고    scopus 로고
    • The role of thiols and disulfides in protein chemical and physical stability
    • Trivedi, M. V., Laurence, J. S., and Siahaan, T. J. (2009) The role of thiols and disulfides in protein chemical and physical stability Curr. Protein Pept. Sci. 10, 614-625 10.2174/138920309789630534
    • (2009) Curr. Protein Pept. Sci. , vol.10 , pp. 614-625
    • Trivedi, M.V.1    Laurence, J.S.2    Siahaan, T.J.3
  • 21
    • 84964296830 scopus 로고    scopus 로고
    • Orthogonal ring-closing alkyne and olefin metathesis for the synthesis of small GTPase-targeting bicyclic peptides
    • Cromm, P. M., Schaubach, S., Spiegel, J., Furstner, A., Grossmann, T. N., and Waldmann, H. (2016) Orthogonal ring-closing alkyne and olefin metathesis for the synthesis of small GTPase-targeting bicyclic peptides Nat. Commun. 7, 11300 10.1038/ncomms11300
    • (2016) Nat. Commun. , vol.7 , pp. 11300
    • Cromm, P.M.1    Schaubach, S.2    Spiegel, J.3    Furstner, A.4    Grossmann, T.N.5    Waldmann, H.6
  • 22
    • 84876702107 scopus 로고    scopus 로고
    • A Perfluoroaryl-Cysteine SNAr Chemistry Approach to Unprotected Peptide Stapling
    • Spokoyny, A. M., Zou, Y., Ling, J. J., Yu, H., Lin, Y.-S., and Pentelute, B. L. (2013) A Perfluoroaryl-Cysteine SNAr Chemistry Approach to Unprotected Peptide Stapling J. Am. Chem. Soc. 135, 5946-5949 10.1021/ja400119t
    • (2013) J. Am. Chem. Soc. , vol.135 , pp. 5946-5949
    • Spokoyny, A.M.1    Zou, Y.2    Ling, J.J.3    Yu, H.4    Lin, Y.-S.5    Pentelute, B.L.6
  • 24
    • 84978747042 scopus 로고    scopus 로고
    • Nitrogen Arylation for Macrocyclization of Unprotected Peptides
    • Lautrette, G., Touti, F., Lee, H. G., Dai, P., and Pentelute, B. L. (2016) Nitrogen Arylation for Macrocyclization of Unprotected Peptides J. Am. Chem. Soc. 138, 8340-8343 10.1021/jacs.6b03757
    • (2016) J. Am. Chem. Soc. , vol.138 , pp. 8340-8343
    • Lautrette, G.1    Touti, F.2    Lee, H.G.3    Dai, P.4    Pentelute, B.L.5
  • 25
    • 84982084133 scopus 로고    scopus 로고
    • Modulation of Backbone Flexibility for Effective Dissociation of Antibacterial and Hemolytic Activity in Cyclic Peptides
    • Oddo, A., Thomsen, T. T., Britt, H. M., Løbner-Olesen, A., Thulstrup, P. W., Sanderson, J. M., and Hansen, P. R. (2016) Modulation of Backbone Flexibility for Effective Dissociation of Antibacterial and Hemolytic Activity in Cyclic Peptides ACS Med. Chem. Lett. 7, 741 10.1021/acsmedchemlett.5b00400
    • (2016) ACS Med. Chem. Lett. , vol.7 , pp. 741
    • Oddo, A.1    Thomsen, T.T.2    Britt, H.M.3    Løbner-Olesen, A.4    Thulstrup, P.W.5    Sanderson, J.M.6    Hansen, P.R.7
  • 28
    • 34848850746 scopus 로고    scopus 로고
    • An efficient, inexpensive, and shelf-stable diazotransfer reagent: Imidazole-1-sulfonyl azide hydrochloride
    • Goddard-Borger, E. D. and Stick, R. V. (2007) An efficient, inexpensive, and shelf-stable diazotransfer reagent: imidazole-1-sulfonyl azide hydrochloride Org. Lett. 9, 3797-3800 10.1021/ol701581g
    • (2007) Org. Lett. , vol.9 , pp. 3797-3800
    • Goddard-Borger, E.D.1    Stick, R.V.2
  • 29
    • 0037870789 scopus 로고    scopus 로고
    • Chromium(VI) Oxide Catalyzed Oxidation of Sulfides to Sulfones with Periodic Acid
    • Xu, L., Cheng, J., and Trudell, M. L. (2003) Chromium(VI) Oxide Catalyzed Oxidation of Sulfides to Sulfones with Periodic Acid J. Org. Chem. 68, 5388-5391 10.1021/jo030031n
    • (2003) J. Org. Chem. , vol.68 , pp. 5388-5391
    • Xu, L.1    Cheng, J.2    Trudell, M.L.3
  • 30
    • 84961654773 scopus 로고    scopus 로고
    • α-Azido Acids in Solid-Phase Peptide Synthesis: Compatibility with Fmoc Chemistry and an Alternative Approach to the Solid Phase Synthesis of Daptomycin Analogs
    • Lohani, C. R., Rasera, B., Scott, B., Palmer, M., and Taylor, S. D. (2016) α-Azido Acids in Solid-Phase Peptide Synthesis: Compatibility with Fmoc Chemistry and an Alternative Approach to the Solid Phase Synthesis of Daptomycin Analogs J. Org. Chem. 81, 2624-2628 10.1021/acs.joc.5b02882
    • (2016) J. Org. Chem. , vol.81 , pp. 2624-2628
    • Lohani, C.R.1    Rasera, B.2    Scott, B.3    Palmer, M.4    Taylor, S.D.5
  • 31
    • 84937518958 scopus 로고    scopus 로고
    • Structure-Based Design of Inhibitors of Protein-Protein Interactions: Mimicking Peptide Binding Epitopes
    • Pelay-Gimeno, M., Glas, A., Koch, O., and Grossmann, T. N. (2015) Structure-Based Design of Inhibitors of Protein-Protein Interactions: Mimicking Peptide Binding Epitopes Angew. Chem., Int. Ed. 54, 8896-8927 10.1002/anie.201412070
    • (2015) Angew. Chem., Int. Ed. , vol.54 , pp. 8896-8927
    • Pelay-Gimeno, M.1    Glas, A.2    Koch, O.3    Grossmann, T.N.4
  • 32
    • 0014592230 scopus 로고
    • Computed circular dichroism spectra for the evaluation of protein conformation
    • Greenfield, N. and Fasman, G. D. (1969) Computed circular dichroism spectra for the evaluation of protein conformation Biochemistry 8, 4108-4116 10.1021/bi00838a031
    • (1969) Biochemistry , vol.8 , pp. 4108-4116
    • Greenfield, N.1    Fasman, G.D.2
  • 33
    • 84873684719 scopus 로고    scopus 로고
    • Global Analysis of Peptide Cyclization Efficiency
    • Thakkar, A., Trinh, T. B., and Pei, D. (2013) Global Analysis of Peptide Cyclization Efficiency ACS Comb. Sci. 15, 120-129 10.1021/co300136j
    • (2013) ACS Comb. Sci. , vol.15 , pp. 120-129
    • Thakkar, A.1    Trinh, T.B.2    Pei, D.3
  • 34
    • 84880069571 scopus 로고    scopus 로고
    • Imidazole-1-sulfonyl Azide-Based Diazo-Transfer Reaction for the Preparation of Azido Solid Supports for Solid-Phase Synthesis
    • Castro, V., Blanco-Canosa, J. B., Rodriguez, H., and Albericio, F. (2013) Imidazole-1-sulfonyl Azide-Based Diazo-Transfer Reaction for the Preparation of Azido Solid Supports for Solid-Phase Synthesis ACS Comb. Sci. 15, 331-334 10.1021/co4000437
    • (2013) ACS Comb. Sci. , vol.15 , pp. 331-334
    • Castro, V.1    Blanco-Canosa, J.B.2    Rodriguez, H.3    Albericio, F.4
  • 36
    • 77649271201 scopus 로고    scopus 로고
    • Bone Marrow-Derived Macrophages (BMM): Isolation and Applications
    • Weischenfeldt, J. and Porse, B. (2008) Bone Marrow-Derived Macrophages (BMM): Isolation and Applications CSH Protoc. 2008, 5080 10.1101/pdb.prot5080
    • (2008) CSH Protoc. , vol.2008 , pp. 5080
    • Weischenfeldt, J.1    Porse, B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.