18F-Labeled wild-type annexin V: comparison of random and site-selective radiolabeling methods

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• 作者：Amanda Perreault ; James C. Knight ; Monica Wang ; Jenilee Way ; Frank Wuest
• 关键词：Wild ; type annexin V ; Fluorine ; 18 ; Apoptosis ; [18F]SFB ; [18F]FBEM
• 刊名：Amino Acids
• 出版年：2016
• 出版时间：January 2016
• 年：2016
• 卷：48
• 期：1
• 页码：65-74
• 全文大小：643 KB
• 参考文献：Belhocine T, Steinmetz N, Hustinx R, Bartsch P, Jerusalem G, Seidel L, Rigo P, Green A (2002) Increased uptake of the apoptosis-imaging agent (99 m)Tc recombinant human Annexin V in human tumors after one course of chemotherapy as a predictor of tumor response and patient prognosis. Clin Cancer Res 8:2766–2774PubMed
  Blankenberg FG (2008) In vivo detection of apoptosis. J Nucl Med 49(Suppl 2):81S–95SPubMed CrossRef
  Blankenberg FG, Katsikis PD, Tait JF, Davis RE, Naumovski L, Ohtsuki K, Kopiwoda S, Abrams MJ, Darkes M, Robbins RC, Maecker HT, Strauss HW (1998) In vivo detection and imaging of phosphatidylserine expression during programmed cell death. Proc Natl Acad Sci USA 95:6349–6354PubMed PubMedCentral CrossRef
  Cai W, Zhang X, Wu Y, Chen X (2006) A thiol-reactive 18F-labeling agent, N-[2-(4-18F-fluorobenzamido)ethyl]maleimide, and synthesis of RGD peptide-based tracer for PET imaging of alpha v beta 3 integrin expression. J Nucl Med 47:1172–1180PubMed PubMedCentral
  De Saint-Hubert M, Wang H, Devos E, Vunckx K, Zhou L, Reutelingsperger C, Verbruggen A, Mortelmans L, Ni Y, Mottaghy FM (2011) Preclinical imaging of therapy response using metabolic and apoptosis molecular imaging. Mol Imaging Biol 13:995–1002PubMed CrossRef
  Grierson JR, Yagle KJ, Eary JF, Tait JF, Gibson DF, Lewellen B, Link JM, Krohn KA (2004) Production of [F-18]fluoroannexin for imaging apoptosis with PET. Bioconjug Chem 15:373–379PubMed CrossRef
  Guo MF, Zhao Y, Tian R, Li L, Guo L, Xu F, Liu YM, He YB, Bai S, Wang J (2009) In vivo 99 mTc-HYNIC-annexin V imaging of early tumor apoptosis in mice after single dose irradiation. J Exp Clin Cancer Res 28:136PubMed PubMedCentral CrossRef
  Hu S, Kiesewetter DO, Zhu L, Guo N, Gao H, Liu G, Hida N, Lang L, Niu G, Chen X (2012) Longitudinal PET imaging of doxorubicin-induced cell death with 18F-annexin V. Mol Imaging Biol 14:762–770PubMed PubMedCentral CrossRef
  Keen HG, Dekker BA, Disley L, Hastings D, Lyons S, Reader AJ, Ottewell P, Watson A, Zweit J (2005) Imaging apoptosis in vivo using 124I-annexin V and PET. Nucl Med Biol 32:395–402PubMed CrossRef
  Lahorte CM, Vanderheyden JL, Steinmetz N, Van de Wiele C, Dierckx RA, Slegers G (2004) Apoptosis-detecting radioligands: current state of the art and future perspectives. Eur J Nucl Med Mol Imaging 31:887–919PubMed CrossRef
  Lehner S, Todica A, Vanchev Y, Uebleis C, Wang H, Herrler T, Wängler C, Cumming P, Böning G, Franz WM, Bartenstein P, Hacker M, Brunner S (2014) In vivo monitoring of parathyroid hormone treatment after myocardial infarction in mice with [68 Ga]annexin A5 and [18F]fluorodeoxyglucose positron emission tomography. Mol Imaging 13. doi:10.​2310/​7290.​2014.​00035
  Li X, Link JM, Stekhova S, Yagle KJ, Smith C, Krohn KA, Tait JF (2008) Site-specific labeling of annexin V with F-18 for apoptosis imaging. Bioconjug Chem 19:1684–1688PubMed PubMedCentral CrossRef
  Mäding P, Füchtner F, Wüst F (2005) Module-assisted synthesis of the bifunctional labelling agent N-succinimidyl 4-[(18)F]fluorobenzoate ([(18)F]SFB). Appl Radiat Isot 63:329–332PubMed CrossRef
  Martin SJ, Reutelingsperger CP, McGahon AJ, Rader JA, van Schie RC, LaFace DM, Green DR (1995) Early redistribution of plasma membrane phosphatidylserine is a general feature of apoptosis regardless of the initiating stimulus: inhibition by overexpression of Bcl-2 and Abl. J Exp Med 182:1545–1556PubMed CrossRef
  Murakami Y, Takamatsu H, Taki J, Tatsumi M, Noda A, Ichise R, Tait JF, Nishimura S (2004) 18F-labelled annexin V: a PET tracer for apoptosis imaging. Eur J Nucl Med Mol Imaging 31:469–474PubMed CrossRef
  Neves AA, Brindle KM (2014) Imaging cell death. J Nucl Med 55:1–4PubMed CrossRef
  Schaper FL, Reutelingsperger CP (2013) 99 mTc-HYNIC-annexin A5 in oncology: evaluating efficacy of anti-cancer therapies. Cancers (Basel) 5:550–568CrossRef
  Smith BA, Smith BD (2012) Biomarkers and molecular probes for cell death imaging and targeted therapeutics. Bioconjug Chem 23:1989–2006PubMed PubMedCentral CrossRef
  Smith G, Carroll L, Aboagye EO (2012) New frontiers in the design and synthesis of imaging probes for PET oncology: current challenges and future directions. Mol Imaging Biol 14:653–666PubMed CrossRef
  Tait JF, Cerqueira MD, Dewhurst TA, Fujikawa K, Ritchie JL, Stratton JR (1994) Evaluation of annexin V as a platelet-directed thrombus targeting agent. Thromb Res 75:491–501PubMed CrossRef
  Tait JF, Brown DS, Gibson DF, Blankenberg FG, Strauss HW (2000) Development and characterization of annexin V mutants with endogenous chelation sites for (99 m) Tc. Bioconjug Chem 11:918–925PubMed CrossRef
  Tait JF, Gibson DF, Smith C (2004) Measurement of the affinity and cooperativity of annexin V-membrane binding under conditions of low membrane occupancy. Anal Biochem 329:112–119PubMed CrossRef
  Tait JF, Smith C, Levashova Z, Patel B, Blankenberg FG, Vanderheyden JL (2006) Improved detection of cell death in vivo with annexin V radiolabeled by site-specific methods. J Nucl Med 47:1546–1553PubMed
  Toretsky J, Levenson A, Weinberg IN, Tait JF, Uren A, Mease RC (2004) Preparation of F-18 labeled annexin V: a potential PET radiopharmaceutical for imaging cell death. Nucl Med Biol 31:747–752PubMed CrossRef
  Vangestel C, Peeters M, Mees G, Oltenfreiter R, Boersma HH, Elsinga PH, Reutelingsperger C, Van Damme N, De Spiegeleer B, Van de Wiele C (2011) In vivo imaging of apoptosis in oncology: an update. Mol Imaging 10:340–358PubMed
  Wängler C, Wängler B, Lehner S, Elsner A, Todica A, Bartenstein P, Hacker M, Schirrmacher R (2011) A universally applicable 68 Ga-labeling technique for proteins. J Nucl Med 52:586–591PubMed CrossRef
  Wuest F, Berndt M, Bergmann R, van den Hoff J, Pietzsch J (2008) Synthesis and application of [18F]FDG-maleimidehexyloxime ([18F]FDG-MHO): a [18F]FDG-based prosthetic group for the chemoselective 18F-labeling of peptides and proteins. Bioconjug Chem 19:1202–1210PubMed CrossRef
  Wuest M, Perreault A, Kapty J, Richter S, Foerster C, Bergman C, Way J, Mercer J, Wuest F (2015) Radiopharmacological evaluation of 18F-labeled phosphatidylserine-binding peptides for molecular imaging of apoptosis. Nucl Med Biol. doi:10.​1016/​j.​nucmedbio.​2015.​06.​011
  Yagle KJ, Eary JF, Tait JF, Grierson JR, Link JM, Lewellen B, Gibson DF, Krohn KA (2005) Evaluation of 18F-annexin V as a PET imaging agent in an animal model of apoptosis. J Nucl Med 46:658–666PubMed
  Zijlstra S, Gunawan J, Burchert W (2003) Synthesis and evaluation of a 18F-labelled recombinant annexin-V derivative, for identification and quantification of apoptotic cells with PET. Appl Radiat Isot 58:201–207PubMed CrossRef
  
• 作者单位：Amanda Perreault (1)
  James C. Knight (1)
  Monica Wang (1)
  Jenilee Way (1)
  Frank Wuest (1)
  
  1. Department of Oncology, University of Alberta, Edmonton, AB, T6G 1Z2, Canada
  
• 刊物类别：Biomedical and Life Sciences
• 刊物主题：Life Sciences
  Biochemistry
  Analytical Chemistry
  Biochemical Engineering
  Life Sciences
  Proteomics
  Neurobiology
  
• 出版者：Springer Wien
• ISSN：1438-2199

文摘

Early stage apoptosis is characterized by the externalization of phosphatidylserine (PS) from the inner leaflet of the plasma membrane to the outer periphery. Consequently, PS represents an excellent target for non-invasive imaging of apoptosis by positron emission tomography. Annexin V is a 36 kDa protein which binds with high affinity to PS. Radiolabeling of wild-type annexin V with fluorine-18 (18F) can be accomplished via random acylation of 23 amine groups (22 lysine residues and one N-terminal amine) with [18F]SFB or site-specific alkylation reaction on cysteine residue at position 315 with maleimide-containing prosthetic groups like [18F]FBEM. The effect upon random and site-directed 18F labeling of annexin V was studied with EL4 mouse lymphoma cells. Both, randomly and site-selectively radiolabeled annexin V demonstrated comparable binding to apoptotic EL4 cells. This finding suggests that the 18F radiolabeling method has no significant effect on the ability of 18F-labeled wild-type annexin V to bind PS in apoptotic cells. Keywords Wild-type annexin V Fluorine-18 Apoptosis [18F]SFB [18F]FBEM