메뉴 건너뛰기




Volumn 40, Issue 2, 2013, Pages 233-239

Evaluation of an integrin αvβ6-specific peptide labeled with [18F]fluorine by copper-free, strain-promoted click chemistry

Author keywords

Copper free; Cyclooctyne; Diagnostic radionuclides; Fluorine 18; Positron; Strain promoted click

Indexed keywords

ALCOHOL; ALPHAVBETA6 INTEGRIN; COPPER; FLUORINE 18; PEPTIDE DERIVATIVE; SODIUM CHLORIDE; TRACER;

EID: 84872927513     PISSN: 09698051     EISSN: 18729614     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2012.10.007     Document Type: Article
Times cited : (58)

References (42)
  • 1
    • 78649325858 scopus 로고    scopus 로고
    • Target-specific delivery of peptide-based probes for PET imaging
    • Chen K., Conti P.S. Target-specific delivery of peptide-based probes for PET imaging. Adv Drug Deliv Rev 2010, 62:1005-1022.
    • (2010) Adv Drug Deliv Rev , vol.62 , pp. 1005-1022
    • Chen, K.1    Conti, P.S.2
  • 3
    • 56249122581 scopus 로고    scopus 로고
    • Synthesis of C-11, F-18, O-15, and N-13 radiolabels for positron emission tomography
    • Miller P.W., Long N.J., Vilar R., Gee A.D. Synthesis of C-11, F-18, O-15, and N-13 radiolabels for positron emission tomography. Angew Chem Int Ed 2008, 47:8998-9033.
    • (2008) Angew Chem Int Ed , vol.47 , pp. 8998-9033
    • Miller, P.W.1    Long, N.J.2    Vilar, R.3    Gee, A.D.4
  • 4
    • 77950457807 scopus 로고    scopus 로고
    • Radiolabelled proteins for positron emission tomography: pros and cons of labelling methods
    • Tolmachev V., Stone-Elander S. Radiolabelled proteins for positron emission tomography: pros and cons of labelling methods. Biochim Biophys Acta 2010, 1800:487-510.
    • (2010) Biochim Biophys Acta , vol.1800 , pp. 487-510
    • Tolmachev, V.1    Stone-Elander, S.2
  • 5
    • 0000096835 scopus 로고    scopus 로고
    • Click chemistry: diverse chemical function from a few good reactions
    • Kolb H.C., Finn M.G., Sharpless K.B. Click chemistry: diverse chemical function from a few good reactions. Angew Chem Int Ed 2001, 40:2004-2021.
    • (2001) Angew Chem Int Ed , vol.40 , pp. 2004-2021
    • Kolb, H.C.1    Finn, M.G.2    Sharpless, K.B.3
  • 6
    • 0002641899 scopus 로고
    • Centenary lecture - 1,3-dipolar cycloadditions
    • Huisgen R. Centenary lecture - 1,3-dipolar cycloadditions. Proc Chem Soc Lond 1961, 357-363.
    • (1961) Proc Chem Soc Lond , pp. 357-363
    • Huisgen, R.1
  • 7
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • Rostovtsev V.V., Green L.G., Fokin V.V., Sharpless K.B. A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew Chem Int Ed 2002, 41:2596-2599.
    • (2002) Angew Chem Int Ed , vol.41 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 8
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
    • Tornøe C.W., Christensen C., Meldal M. Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J Org Chem 2002, 67:3057-3064.
    • (2002) J Org Chem , vol.67 , pp. 3057-3064
    • Tornøe, C.W.1    Christensen, C.2    Meldal, M.3
  • 9
    • 51049094897 scopus 로고    scopus 로고
    • Cu-catalyzed azide-alkyne cycloaddition
    • Meldal M., Tornøe C.W. Cu-catalyzed azide-alkyne cycloaddition. Chem Rev 2008, 108:2952-3015.
    • (2008) Chem Rev , vol.108 , pp. 2952-3015
    • Meldal, M.1    Tornøe, C.W.2
  • 13
    • 67650816377 scopus 로고    scopus 로고
    • Growing applications of "click chemistry" for bioconjugation in contemporary biomedical research
    • Nwe K., Brechbiel M.W. Growing applications of "click chemistry" for bioconjugation in contemporary biomedical research. Cancer Biother Radiopharm 2009, 24:289-302.
    • (2009) Cancer Biother Radiopharm , vol.24 , pp. 289-302
    • Nwe, K.1    Brechbiel, M.W.2
  • 14
    • 68149154419 scopus 로고    scopus 로고
    • Recent applications of click chemistry for the synthesis of radiotracers for molecular imaging
    • Mamat C., Ramenda T., Wuest F.R. Recent applications of click chemistry for the synthesis of radiotracers for molecular imaging. Mini-Rev Org Chem 2009, 6:21-34.
    • (2009) Mini-Rev Org Chem , vol.6 , pp. 21-34
    • Mamat, C.1    Ramenda, T.2    Wuest, F.R.3
  • 15
    • 70350304285 scopus 로고    scopus 로고
    • A "click chemistry" approach to the efficient synthesis of multiple imaging probes derived from a single precursor
    • Mindt T.L., Müller C., Stuker F., Salazar J.F., Hohn A., Mueggler T., et al. A "click chemistry" approach to the efficient synthesis of multiple imaging probes derived from a single precursor. Bioconjug Chem 2009, 20:1940-1949.
    • (2009) Bioconjug Chem , vol.20 , pp. 1940-1949
    • Mindt, T.L.1    Müller, C.2    Stuker, F.3    Salazar, J.F.4    Hohn, A.5    Mueggler, T.6
  • 16
    • 80054808224 scopus 로고    scopus 로고
    • Preparation of F-18-labeled peptides using the copper(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition
    • Gill H.S., Marik J. Preparation of F-18-labeled peptides using the copper(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition. Nat Protoc 2011, 6:1718-1725.
    • (2011) Nat Protoc , vol.6 , pp. 1718-1725
    • Gill, H.S.1    Marik, J.2
  • 17
    • 84860703203 scopus 로고    scopus 로고
    • Biodistribution and radiation dosimetry of the integrin marker F-18-RGD-K5 determined from whole-body PET/CT in monkeys and humans
    • Doss M., Kolb H.C., Zhang J.J., Belanger M.J., Stubbs J.B., Stabin M.G., et al. Biodistribution and radiation dosimetry of the integrin marker F-18-RGD-K5 determined from whole-body PET/CT in monkeys and humans. J Nucl Med 2012, 53:787-795.
    • (2012) J Nucl Med , vol.53 , pp. 787-795
    • Doss, M.1    Kolb, H.C.2    Zhang, J.J.3    Belanger, M.J.4    Stubbs, J.B.5    Stabin, M.G.6
  • 18
    • 9344227358 scopus 로고    scopus 로고
    • A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems
    • Agard N.J., Prescher J.A., Bertozzi C.R. A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. J Am Chem Soc 2004, 126:15046-15047.
    • (2004) J Am Chem Soc , vol.126 , pp. 15046-15047
    • Agard, N.J.1    Prescher, J.A.2    Bertozzi, C.R.3
  • 20
    • 77949863611 scopus 로고    scopus 로고
    • Cu-free click cycloaddition reactions in chemical biology
    • Jewett J.C., Bertozzi C.R. Cu-free click cycloaddition reactions in chemical biology. Chem Soc Rev 2010, 39:1272-1279.
    • (2010) Chem Soc Rev , vol.39 , pp. 1272-1279
    • Jewett, J.C.1    Bertozzi, C.R.2
  • 21
    • 41049098451 scopus 로고    scopus 로고
    • Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast Huisgen cycloadditions
    • Ning X.H., Guo J., Wolfert M.A., Boons G.J. Visualizing metabolically labeled glycoconjugates of living cells by copper-free and fast Huisgen cycloadditions. Angew Chem Int Ed 2008, 47:2253-2255.
    • (2008) Angew Chem Int Ed , vol.47 , pp. 2253-2255
    • Ning, X.H.1    Guo, J.2    Wolfert, M.A.3    Boons, G.J.4
  • 22
    • 78649279718 scopus 로고    scopus 로고
    • Surface functionalization using catalyst-free azide-alkyne cycloaddition
    • Kuzmin A., Poloukhtine A., Wolfert M.A., Popik V.V. Surface functionalization using catalyst-free azide-alkyne cycloaddition. Bioconjug Chem 2010, 21:2076-2085.
    • (2010) Bioconjug Chem , vol.21 , pp. 2076-2085
    • Kuzmin, A.1    Poloukhtine, A.2    Wolfert, M.A.3    Popik, V.V.4
  • 23
    • 43249099890 scopus 로고    scopus 로고
    • In vivo imaging of membrane-associated glycans in developing zebrafish
    • Laughlin S.T., Baskin J.M., Amacher S.L., Bertozzi C.R. In vivo imaging of membrane-associated glycans in developing zebrafish. Science 2008, 320:664-667.
    • (2008) Science , vol.320 , pp. 664-667
    • Laughlin, S.T.1    Baskin, J.M.2    Amacher, S.L.3    Bertozzi, C.R.4
  • 24
    • 77952378094 scopus 로고    scopus 로고
    • Synthesis of a DOTA-biotin conjugate for radionuclide chelation via Cu-free click chemistry
    • Schultz M.K., Parameswarappa S.G., Pigge F.C. Synthesis of a DOTA-biotin conjugate for radionuclide chelation via Cu-free click chemistry. Org Lett 2010, 12:2398-2401.
    • (2010) Org Lett , vol.12 , pp. 2398-2401
    • Schultz, M.K.1    Parameswarappa, S.G.2    Pigge, F.C.3
  • 25
    • 83455172909 scopus 로고    scopus 로고
    • Copper-free click for PET: Rapid 1,3-dipolar cycloadditions with a fluorine-18 cyclooctyne
    • Carpenter R.D., Hausner S.H., Sutcliffe J.L. Copper-free click for PET: Rapid 1,3-dipolar cycloadditions with a fluorine-18 cyclooctyne. ACS Med Chem Lett 2011, 2:885-889.
    • (2011) ACS Med Chem Lett , vol.2 , pp. 885-889
    • Carpenter, R.D.1    Hausner, S.H.2    Sutcliffe, J.L.3
  • 26
    • 80053955813 scopus 로고    scopus 로고
    • Copper-free click chemistry with the short-lived positron emitter fluorine-18
    • Bouvet V., Wuest M., Wuest F. Copper-free click chemistry with the short-lived positron emitter fluorine-18. Org Biomol Chem 2011, 9:7393-7399.
    • (2011) Org Biomol Chem , vol.9 , pp. 7393-7399
    • Bouvet, V.1    Wuest, M.2    Wuest, F.3
  • 28
    • 80255137225 scopus 로고    scopus 로고
    • [F-18] Azadibenzocyclooctyne ([F-18]ADIBO): A biocompatible radioactive labeling synthon for peptides using catalyst free [3+2] cycloaddition
    • Arumugam S., Chin J., Schirrmacher R., Popik V.V., Kostikov A.P. [F-18] Azadibenzocyclooctyne ([F-18]ADIBO): A biocompatible radioactive labeling synthon for peptides using catalyst free [3+2] cycloaddition. Bioorg Med Chem Lett 2011, 21:6987-6991.
    • (2011) Bioorg Med Chem Lett , vol.21 , pp. 6987-6991
    • Arumugam, S.1    Chin, J.2    Schirrmacher, R.3    Popik, V.V.4    Kostikov, A.P.5
  • 29
    • 67651006249 scopus 로고    scopus 로고
    • Targeted in vivo imaging of integrin alpha(v)beta(6) with an improved radiotracer and its relevance in a pancreatic tumor model
    • Hausner S.H., Abbey C.K., Bold R.J., Gagnon M.K., Marik J., Marshall J.F., et al. Targeted in vivo imaging of integrin alpha(v)beta(6) with an improved radiotracer and its relevance in a pancreatic tumor model. Cancer Res 2009, 69:5843-5850.
    • (2009) Cancer Res , vol.69 , pp. 5843-5850
    • Hausner, S.H.1    Abbey, C.K.2    Bold, R.J.3    Gagnon, M.K.4    Marik, J.5    Marshall, J.F.6
  • 31
    • 70249086983 scopus 로고    scopus 로고
    • Defining the role of integrin alpha v beta 6 in cancer
    • Bandyopadhyay A., Raghavan S. Defining the role of integrin alpha v beta 6 in cancer. Curr Drug Targets 2009, 10:645-652.
    • (2009) Curr Drug Targets , vol.10 , pp. 645-652
    • Bandyopadhyay, A.1    Raghavan, S.2
  • 34
    • 0017157455 scopus 로고
    • New micro-test for detection of incomplete coupling reactions in solid-phase peptide-synthesis using 2,4,6-trinitrobenzene-sulphonic acid
    • Hancock W.S., Battersby J.E. New micro-test for detection of incomplete coupling reactions in solid-phase peptide-synthesis using 2,4,6-trinitrobenzene-sulphonic acid. Anal Biochem 1976, 71:260-264.
    • (1976) Anal Biochem , vol.71 , pp. 260-264
    • Hancock, W.S.1    Battersby, J.E.2
  • 36
    • 77950298585 scopus 로고    scopus 로고
    • Biodistribution and stability studies of [F-18]Fluoroethylrhodamine B, a potential PET myocardial perfusion agent
    • Gottumukkala V., Heinrich T.K., Baker A., Dunning P., Fahey F.H., Treves S.T., et al. Biodistribution and stability studies of [F-18]Fluoroethylrhodamine B, a potential PET myocardial perfusion agent. Nucl Med Biol 2010, 37:365-370.
    • (2010) Nucl Med Biol , vol.37 , pp. 365-370
    • Gottumukkala, V.1    Heinrich, T.K.2    Baker, A.3    Dunning, P.4    Fahey, F.H.5    Treves, S.T.6
  • 40
    • 80052989876 scopus 로고    scopus 로고
    • From mechanism to mouse: a tale of two bioorthogonal reactions
    • Sletten E.M., Bertozzi C.R. From mechanism to mouse: a tale of two bioorthogonal reactions. Acc Chem Res 2011, 44:666-676.
    • (2011) Acc Chem Res , vol.44 , pp. 666-676
    • Sletten, E.M.1    Bertozzi, C.R.2
  • 42
    • 80053031240 scopus 로고    scopus 로고
    • Biomedical applications of tetrazine cycloadditions
    • Devaraj N.K., Weissleder R. Biomedical applications of tetrazine cycloadditions. Acc Chem Res 2011, 44:816-827.
    • (2011) Acc Chem Res , vol.44 , pp. 816-827
    • Devaraj, N.K.1    Weissleder, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.