메뉴 건너뛰기




Volumn 43, Issue 4, 2012, Pages 1431-1443

Site-selective radiolabeling of peptides by 18F- fluorobenzoylation with [18F]SFB in solution and on solid phase: Acomparative study

Author keywords

Fluorine 18; Positron emission tomography; Regioselectivity; Solid phase synthesis

Indexed keywords

FLUORINE 18; LYSINE; N SUCCINIMIDYL 4 FLUOROBENZOATE F 18; PEPTIDE; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

EID: 84867574516     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-012-1216-z     Document Type: Article
Times cited : (32)

References (40)
  • 1
    • 33645858005 scopus 로고    scopus 로고
    • Agonists and antagonists of protease activated receptors (PARs)
    • 16475935 10.2174/092986706775476070 1:CAS:528:DC%2BD28XhtVequrg%3D
    • Barry GD, Le GT, Fairlie DP (2006) Agonists and antagonists of protease activated receptors (PARs). Curr Med Chem 13:243-265
    • (2006) Curr Med Chem , vol.13 , pp. 243-265
    • Barry, G.D.1    Le, G.T.2    Fairlie, D.P.3
  • 4
    • 49849087072 scopus 로고    scopus 로고
    • Chemistry with [F-18]fluoride ion
    • 10.1002/ejoc.200800114
    • Cai LS, Lu SY, Pike VW (2008) Chemistry with [F-18]fluoride ion. Eur J Org Chem 17:2853-2873
    • (2008) Eur J Org Chem , vol.17 , pp. 2853-2873
    • Cai, L.S.1    Lu, S.Y.2    Pike, V.W.3
  • 5
    • 78649325858 scopus 로고    scopus 로고
    • Target-specific delivery of peptide-based probes for PET imaging
    • 10.1016/j.addr.2010.09.004 1:CAS:528:DC%2BC3cXhsVGitb7N
    • Chen K, Conti PS (2010) Target-specific delivery of peptide-based probes for PET imaging. Adv Drug Delivery Rev 62:1005-1022
    • (2010) Adv Drug Delivery Rev , vol.62 , pp. 1005-1022
    • Chen, K.1    Conti, P.S.2
  • 6
    • 37549017344 scopus 로고    scopus 로고
    • Three-dimensional structure of the EphB2 receptor in complex with an antagonistic peptide reveals Anovel mode of inhibition
    • 17897949 10.1074/jbc.M706340200 1:CAS:528:DC%2BD2sXhsVSgtrvE
    • Chrencik JE, Brooun A, Recht MI, Nicola G, Davis LK, Abagyan R, Widmer H, Pasquale EB, Kuhn P (2007) Three-dimensional structure of the EphB2 receptor in complex with an antagonistic peptide reveals Anovel mode of inhibition. J Biol Chem 282:36505-36513
    • (2007) J Biol Chem , vol.282 , pp. 36505-36513
    • Chrencik, J.E.1    Brooun, A.2    Recht, M.I.3    Nicola, G.4    Davis, L.K.5    Abagyan, R.6    Widmer, H.7    Pasquale, E.B.8    Kuhn, P.9
  • 7
    • 70349278426 scopus 로고    scopus 로고
    • 'Click-labelling' in PET-radiochemistry
    • 10.1002/jlcr.1656 1:CAS:528:DC%2BD1MXhtFGku7zE
    • Glaser M, Robins EG (2009) 'Click-labelling' in PET-radiochemistry. J Label Compd Radiopharm 52:407-414
    • (2009) J Label Compd Radiopharm , vol.52 , pp. 407-414
    • Glaser, M.1    Robins, E.G.2
  • 8
    • 68049090943 scopus 로고    scopus 로고
    • Two-step radiosynthesis of [F-18]N-succinimidyl-4-fluorobenzoate ([F-18]SFB)
    • 10.1002/jlcr.1601 1:CAS:528:DC%2BD1MXps1ehtbs%3D
    • Glaser M, Arstad E, Luthra SK, Robins EG (2009) Two-step radiosynthesis of [F-18]N-succinimidyl-4-fluorobenzoate ([F-18]SFB). J Label Compd Radiopharm 52:327-330
    • (2009) J Label Compd Radiopharm , vol.52 , pp. 327-330
    • Glaser, M.1    Arstad, E.2    Luthra, S.K.3    Robins, E.G.4
  • 10
    • 0018581198 scopus 로고
    • Role of the amino-terminal extra-helical region of type-I collagen in directing the 4D overlap in fibrillogenesis
    • 10.1002/bip.1979.360181208 1:CAS:528:DyaL3cXntFeltw%3D%3D
    • Helseth DL, Lechner JH, Veis A(1979) Role of the amino-terminal extra-helical region of type-I collagen in directing the 4D overlap in fibrillogenesis. Biopolymers 18:3005-3014
    • (1979) Biopolymers , vol.18 , pp. 3005-3014
    • Helseth, D.L.1    Lechner, J.H.2    Veis, A.3
  • 12
    • 37349109209 scopus 로고    scopus 로고
    • Expression, purification and fluorine-18 radiolabeling of recombinant S100 proteinspotential probes for molecular imaging of receptor for advanced glycation endproducts (RAGE) in vivo
    • 10.1016/j.pep.2007.10.009 1:CAS:528:DC%2BD2sXhsVOltrzI
    • Hoppmann S, Haase C, Richter S, Pietzsch J (2008) Expression, purification and fluorine-18 radiolabeling of recombinant S100 proteinspotential probes for molecular imaging of receptor for advanced glycation endproducts (RAGE) in vivo. Protein Expres Purif 57:143-152
    • (2008) Protein Expres Purif , vol.57 , pp. 143-152
    • Hoppmann, S.1    Haase, C.2    Richter, S.3    Pietzsch, J.4
  • 14
    • 0014772602 scopus 로고
    • Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides
    • 5443684 10.1016/0003-2697(70)90146-6 1:CAS:528:DyaE3cXhtVWjur0%3D
    • Kaiser E, Colescott RL, Bossinger CD, Cook PI (1970) Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides. Anal Biochem 34:595-598
    • (1970) Anal Biochem , vol.34 , pp. 595-598
    • Kaiser, E.1    Colescott, R.L.2    Bossinger, C.D.3    Cook, P.I.4
  • 16
    • 0025103048 scopus 로고
    • Acleavage method which minimizes side reactions following Fmoc solid-phase peptide synthesis
    • 10.1111/j.1399-3011.1990.tb00976.x 1:CAS:528:DyaK3MXisVGktg%3D%3D
    • King DS, Fields CG, Fields GB (1990) Acleavage method which minimizes side reactions following Fmoc solid-phase peptide synthesis. Int J Peptide Protein Res 36:255-266
    • (1990) Int J Peptide Protein Res , vol.36 , pp. 255-266
    • King, D.S.1    Fields, C.G.2    Fields, G.B.3
  • 17
    • 20344376236 scopus 로고    scopus 로고
    • EphB receptor-binding peptides identified by phage display enable design of an antagonist with ephrin-like affinity
    • 15722342 10.1074/jbc.M500363200 1:CAS:528:DC%2BD2MXjsFOgurs%3D
    • Koolpe M, Burgess R, Dail M, Pasquale EB (2005) EphB receptor-binding peptides identified by phage display enable design of an antagonist with ephrin-like affinity. J Biol Chem 280:17301-17311
    • (2005) J Biol Chem , vol.280 , pp. 17301-17311
    • Koolpe, M.1    Burgess, R.2    Dail, M.3    Pasquale, E.B.4
  • 18
    • 77954337660 scopus 로고    scopus 로고
    • The challenge of labeling macromolecules with fluorine-18: Three decades of research
    • 10.2174/1874471011003030174 1:CAS:528:DC%2BC3cXhtVahsrrE
    • Kuhnast B, Dolle F (2010) The challenge of labeling macromolecules with fluorine-18: Three decades of research. Curr Radiopharm 3:174-201
    • (2010) Curr Radiopharm , vol.3 , pp. 174-201
    • Kuhnast, B.1    Dolle, F.2
  • 19
    • 78649320159 scopus 로고    scopus 로고
    • Radiopharmaceutical chemistry for positron emission tomography
    • 10.1016/j.addr.2010.09.007 1:CAS:528:DC%2BC3cXhsVGitb7P
    • Li Z, Conti PS (2010) Radiopharmaceutical chemistry for positron emission tomography. Adv Drug Delivery Rev 62:1031-1051
    • (2010) Adv Drug Delivery Rev , vol.62 , pp. 1031-1051
    • Li, Z.1    Conti, P.S.2
  • 20
    • 21844465098 scopus 로고    scopus 로고
    • Module-Assisted synthesis of the bifunctional labelling agent N-succinimidyl 4-[F-18]fluorobenzoate ([F-18]SFB)
    • 15949940 10.1016/j.apradiso.2005.03.005
    • Mäding P, Füchtner F, Wüst F (2005) Module-Assisted synthesis of the bifunctional labelling agent N-succinimidyl 4-[F-18]fluorobenzoate ([F-18]SFB). Appl Radiat Isot 63:329-332
    • (2005) Appl Radiat Isot , vol.63 , pp. 329-332
    • Mäding, P.1    Füchtner, F.2    Wüst, F.3
  • 21
    • 68149154419 scopus 로고    scopus 로고
    • Recent applications of click chemistry for the synthesis of radiotracers for molecular imaging
    • 10.2174/157019309787316148 1:CAS:528:DC%2BD1MXks1Chsbc%3D
    • Mamat C, Ramenda T, Wuest FR (2009) Recent applications of click chemistry for the synthesis of radiotracers for molecular imaging. Mini-Rev Org Chem 6:21-34
    • (2009) Mini-Rev Org Chem , vol.6 , pp. 21-34
    • Mamat, C.1    Ramenda, T.2    Wuest, F.R.3
  • 23
    • 0027978741 scopus 로고
    • Modulation of lysyl oxidase activity toward peptidyl lysine by vicinal dicarboxylic amino acid residues. Implications for collagen cross-linking
    • 7915281 1:CAS:528:DyaK2cXlvF2htL0%3D
    • Nagan N, Kagan HM (1994) Modulation of lysyl oxidase activity toward peptidyl lysine by vicinal dicarboxylic amino acid residues. Implications for collagen cross-linking. J Biol Chem 269:22366-22371
    • (1994) J Biol Chem , vol.269 , pp. 22366-22371
    • Nagan, N.1    Kagan, H.M.2
  • 24
    • 78650394438 scopus 로고    scopus 로고
    • Molecular tracers for the PET and SPECT imaging of disease
    • 20818455 10.1039/b922628c
    • Pimlott SL, Sutherland A(2010) Molecular tracers for the PET and SPECT imaging of disease. Chem Soc Rev 40:149-162
    • (2010) Chem Soc Rev , vol.40 , pp. 149-162
    • Pimlott, S.L.1    Sutherland, A.2
  • 26
    • 75649102867 scopus 로고    scopus 로고
    • Fluorine-18 labeling of phosphopeptides: Apotential approach for the evaluation of phosphopeptide metabolism in vivo
    • 10.1002/bip.21263 1:CAS:528:DC%2BD1MXhsVehsL%2FE
    • Richter S, Bergmann R, Pietzsch J, Ramenda T, Steinbach J, Wuest F (2009) Fluorine-18 labeling of phosphopeptides: Apotential approach for the evaluation of phosphopeptide metabolism in vivo. Biopolymers (Pept Sci) 92:479-488
    • (2009) Biopolymers (Pept Sci) , vol.92 , pp. 479-488
    • Richter, S.1    Bergmann, R.2    Pietzsch, J.3    Ramenda, T.4    Steinbach, J.5    Wuest, F.6
  • 27
    • 77954414562 scopus 로고    scopus 로고
    • The click chemistry approach applied to fluorine-18
    • 10.2174/1874471011003030202
    • Ross TL (2010) The click chemistry approach applied to fluorine-18. Curr Radiopharm 3:243-247
    • (2010) Curr Radiopharm , vol.3 , pp. 243-247
    • Ross, T.L.1
  • 28
    • 84873982131 scopus 로고    scopus 로고
    • Peptide radiopharmaceuticals
    • H.J. Wester (eds) SCINTOMICS Print Media and Publishing Fürstenfeldbruck
    • Schottelius M (2010) Peptide radiopharmaceuticals. In: Wester HJ (ed) Pharmaceutical radiochemistry (I). SCINTOMICS Print Media and Publishing, Fürstenfeldbruck, pp 163-212
    • (2010) Pharmaceutical Radiochemistry (I) , pp. 163-212
    • Schottelius, M.1
  • 30
    • 4544349166 scopus 로고    scopus 로고
    • Consecutive cyclic pentapeptide modules form short α-helices that are very stable to water and denaturants
    • 10.1002/anie.200352659 1:CAS:528:DC%2BD2cXksVCgtbk%3D
    • Shepherd NE, Abbenante G, Fairlie DP (2004) Consecutive cyclic pentapeptide modules form short α-helices that are very stable to water and denaturants. Angew Chem Int Ed 43:2687-2690
    • (2004) Angew Chem Int Ed , vol.43 , pp. 2687-2690
    • Shepherd, N.E.1    Abbenante, G.2    Fairlie, D.P.3
  • 31
    • 0034679765 scopus 로고    scopus 로고
    • Solid-phase synthesis of [F-18]labelled peptides for positron emission tomography
    • 10915036 10.1016/S0960-894X(00)00179-7 1:CAS:528:DC%2BD3cXkvFKju7o%3D
    • Sutcliffe-Goulden JL, O'Doherty MJ, Bansal SS (2000) Solid-phase synthesis of [F-18]labelled peptides for positron emission tomography. Bioorg Med Chem Lett 10:1501-1503
    • (2000) Bioorg Med Chem Lett , vol.10 , pp. 1501-1503
    • Sutcliffe-Goulden, J.L.1    O'Doherty, M.J.2    Bansal, S.S.3
  • 34
    • 77956565552 scopus 로고    scopus 로고
    • Afacile automated synthesis of N-succinimidyl 4-[F-18]fluorobenzoate ([F-18]SFB) for F-18-labeled cell-penetrating peptide as PET tracer
    • 10.1002/jlcr.1758 1:CAS:528:DC%2BC3cXptlWksLk%3D
    • Tang GH, Tang XL, Wang XL (2010) Afacile automated synthesis of N-succinimidyl 4-[F-18]fluorobenzoate ([F-18]SFB) for F-18-labeled cell-penetrating peptide as PET tracer. J Label Compd Radiopharm 53:543-547
    • (2010) J Label Compd Radiopharm , vol.53 , pp. 543-547
    • Tang, G.H.1    Tang, X.L.2    Wang, X.L.3
  • 35
    • 77950457807 scopus 로고    scopus 로고
    • Radiolabelled proteins for positron emission tomography: Pros and cons of labelling methods
    • 20153401 10.1016/j.bbagen.2010.02.002 1:CAS:528:DC%2BC3cXjt1Gqur0%3D
    • Tolmachev V, Stone-Elander S (2010) Radiolabelled proteins for positron emission tomography: pros and cons of labelling methods. Biochim Biophys Acta 1800:487-510
    • (2010) Biochim Biophys Acta , vol.1800 , pp. 487-510
    • Tolmachev, V.1    Stone-Elander, S.2
  • 36
    • 34248632788 scopus 로고    scopus 로고
    • Synthesis of N-succinimidyl 4-[F-18] fluorobenzoate, an agent for labeling proteins and peptides with F-18
    • 17487148 10.1038/nprot.2006.264 1:CAS:528:DC%2BD2sXhtFagtrbE
    • Vaidyanathan G, Zalutsky MR (2006) Synthesis of N-succinimidyl 4-[F-18] fluorobenzoate, an agent for labeling proteins and peptides with F-18. Nat Protoc 1:1655-1661
    • (2006) Nat Protoc , vol.1 , pp. 1655-1661
    • Vaidyanathan, G.1    Zalutsky, M.R.2
  • 37
    • 77953371532 scopus 로고    scopus 로고
    • Phenotypic screening of phylomer peptide libraries derived from genome fragments to identify and validate new targets and therapeutics
    • 21425969 10.4155/fmc.09.28 1:CAS:528:DC%2BC3cXhtlKhu7g%3D
    • Watt PM (2009) Phenotypic screening of phylomer peptide libraries derived from genome fragments to identify and validate new targets and therapeutics. Future Med Chem 1:257-265
    • (2009) Future Med Chem , vol.1 , pp. 257-265
    • Watt, P.M.1
  • 38
    • 39049192745 scopus 로고    scopus 로고
    • Fluorine-18 labeling of peptides and proteins
    • A. Schubiger M. Friebe L. Lehmann (eds) Springer New York
    • Wester HJ, Schottelius M (2007) Fluorine-18 labeling of peptides and proteins. In: Schubiger PA, Friebe M, Lehmann L (eds) PET Chemistry: the driving force in molecular imaging. Springer, New York, pp 79-111
    • (2007) PET Chemistry: The Driving Force in Molecular Imaging , pp. 79-111
    • Wester, H.J.1    Schottelius, M.2
  • 40
    • 0029945878 scopus 로고    scopus 로고
    • Acomparative study of NCA fluorine-18 labeling of proteins via acylation and photochemical conjugation
    • 8782249 10.1016/0969-8051(96)00017-0 1:CAS:528:DyaK28Xjs1Sgtbo%3D
    • Wester HJ, Hamacher K, Stöcklin G (1996) Acomparative study of NCA fluorine-18 labeling of proteins via acylation and photochemical conjugation. Nucl Med Biol 23:365-372
    • (1996) Nucl Med Biol , vol.23 , pp. 365-372
    • Wester, H.J.1    Hamacher, K.2    Stöcklin, G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.