Fully automated synthesis procedure of 4-[18F]fluorobenzaldehyde by commercial synthesizer: amino-oxi peptide labelling prosthetic group (429 views)
Applied Radiation And Isotopes (ISSN: 1872-9800, 0969-8043, 0969-8043linking), 2009 Sep; 67(9): 1664-1669.
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Paper type: Journal Article,
Impact factor: 1.094, 5-year impact factor: 1.101
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-67349087391&partnerID=40&md5=a9dbf09c6967fd44dbe1a7dbdbc546c2
Keywords: 18f, Automated Synthesis System, Peptides, Radiohalogenation, Activity Recovery, Automatic Synthesis, Clinical Routine, Functionalized, One-Pot Synthesis, Prosthetic Groups, Radiochemical Purity, Radiochemical Yield, Solid-Phase Extraction, Amination, Projectiles, Purification, 4 Fluorobenzaldehyde F 18, Phenyl Group, Radioisotope, Unclassified Drug, Article, Chemical Labeling, Drug Purity, Drug Synthesis, Priority Journal, Radioactivity, Reactor, Solid Phase Extraction, Fluorine Radioisotopes, Isotope Labeling, Radiopharmaceuticals, Benzaldehydes Chemistry , Peptides Chemistry , Radiopharmaceuticals Chemistry,
Affiliations:
*** IBB - CNR ***
IBB-CNR, Edificio 10, Via Pansini 5, Napoli, Italy. antonio.speranza@hotmail.com
Dipartimento di Scienze Biomorfologiche e Funzionali, Università degli Studi di Napoli Federico II, Edificio 10, Via Pansini 5, Napoli, Italy
References:
Bergmann, R., Scheunemann, M., Heichert, C., Biodistribution and catabolism of 18F-labelled neurotensin (8-13) analogs (2002) Nucl. Med. Biol., 29, pp. 61-7
Berndt, M., Pietzsch, J., Wuest, F., Labeling of low-density lipoproteins using the 18F-labeled thiol-reactive reagent N-[6-(4-[18F]fluorobenzylidene)aminooxyhexyl]maleimide (2007) Nucl. Med. Biol., 34, pp. 5-15
Bruus-Jensen, K., Poethko, T., Schottelius, M., Hauser, A., Schwaiger, M., Wester, H.J., Chemoselective hydrazone formation between HYNIC-functionalized peptides and 18F-fluorinated aldehydes (2006) Nucl. Med. Biol., 33, pp. 173-183
Fredriksson, A., Ekberg, K., Ingvar, M., Johansson, B.L., Wahren, J., Stone-Elander, S., In vivo biodistribution and pharmacokinetics of 18F-labeled human C-peptide: evaluation in monkeys using positron emission tomography (2002) Life Sci., 71, pp. 1361-1370
Haubner, R., Wester, H.J., Weber, W.A., Noninvasive imaging of alpha(v)beta3 integrin expression using 18F-labeled RGD-containing glycopeptide and positron emission tomography (2001) Cancer Res., 61, pp. 1781-1785
Iwata, R., Pascali, C., Bogni, A., A new convenient method for the preparation of 4-[18F]fluorobenzylhalides (2000) Appl. Radiat. Isot., 52, pp. 87-92
Katounina, T., Besret, L., Dhilly, M., Petit-Tabouè, M.C., Barbelivien, A., Baron, J.C., Dauphin, F., Barrè, L., Synthesis and biological investigation of [18F]MR18445, a 5-HT3 receptor partial agonist (1998) Bioorg. Med. Chem., 6, pp. 789-795
Lee, Y.S., Jeong, J.M., Kim, H.W., Chang, Y.S., Kim, Y.J., Hong, M.K., Rai, G.B., Suh, Y.G., An improved method of 18F peptide labeling: hydrazone formation with HYNIC-conjugated c(RGDyK) (2006) Nucl. Med. Biol., 33, pp. 677-683
Lemaire, C., Damhaut, P., Plenevaux, A., Comar, D., Enantioselective synthesis of 6-[fluorine-18]-fluoro-l-dopa from no-carrier-added fluorine-18-fluoride (1997) J. Nucl. Med., 35, pp. 1996-2002
Mading, P., Fuchter, F., Wust, F., Module-assisted synthesis of the bifunctional labelling agent N-succinimidyl 4-[18F]fluorobenzoate ([18F]SFB) (2005) Appl. Radiat. Isot., 63, pp. 329-332
Marik, J., Sutcliffe, L.J., Fully automated preparation of n.c.a. 4-[18F]fluorobenzoic acid and N-succinimidyl 4-[18F]fluorobenzoate using a Siemens/CTI chemistry process control unit (CPCU) (2007) Appl. Radiat. Isot., 65, pp. 199-203
Okarvi, S.M., Recent progress in fluorine-18 labelled peptide radiopharmaceuticals (2001) Eur. J. Nucl. Med., 28, pp. 929-938
Schildan, A., Patt, M., Sabri, O., Synthesis procedure for routine production of 2-[18F]fluoro-3-(2(S)-azetidinylmethoxy)pyridine (2-[18F]F-A-85380) (2007) Appl. Radiat. Isot., 65, pp. 1244-1248
Stöcklin, G.L., Is there a future for clinical fluorine-18 radiopharmaceuticals (excluding FDG)? (1998) Eur. J. Nucl. Med., 25, pp. 1612-1616
Stöcklin, G., Wester, H.J., Strategies for radioligand development: Peptides for tumor targeting (1998) Positron Emission Tomography: A Critical Assessment of Recent Trends, pp. 57-90. , Gulyas, B, Müller-Gärtner, H.W, Eds, Kluwer Academic, Dordrecht, The Netherlands, pp
Toyokuni, T., Walsh, J.S., Dominguez, A., Phelps, M.E., Barrio, J.R., Gambhir, S.S., Satyamurthy, N., Synthesis of a new heterobifunctional linker, N-[4-(aminooxy)butyl]maleimide, for facile access to a thiol-reactive 18F-labeling agent (2003) Bioconjugate Chem., 14 (6), pp. 1253-1259
Lee, Y. S., Jeong, J. M., Kim, H. W., Chang, Y. S., Kim, Y. J., Hong, M. K., Rai, G. B., Suh, Y. G., An improved method of 18F peptide labeling: hydrazone formation with HYNIC-conjugated c (RGDyK) (2006) Nucl. Med. Biol., 33, pp. 677-683
Okarvi, S. M., Recent progress in fluorine-18 labelled peptide radiopharmaceuticals (2001) Eur. J. Nucl. Med., 28, pp. 929-938
St cklin, G. L., Is there a future for clinical fluorine-18 radiopharmaceuticals (excluding FDG)? (1998) Eur. J. Nucl. Med., 25, pp. 1612-1616
St cklin, G., Wester, H. J., Strategies for radioligand development: Peptides for tumor targeting (1998) Positron Emission Tomography: A Critical Assessment of Recent Trends, pp. 57-90. , Gulyas, B, M ller-G rtner, H. W, Eds, Kluwer Academic, Dordrecht, The Netherlands, pp
Applied Radiation And Isotopes (ISSN: 1872-9800, 0969-8043, 0969-8043linking), 2009 Sep; 67(9): 1664-1669.
Export to BibTeX Export to EndNote
Paper type: Journal Article,
Impact factor: 1.094, 5-year impact factor: 1.101
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-67349087391&partnerID=40&md5=a9dbf09c6967fd44dbe1a7dbdbc546c2
Keywords: 18f, Automated Synthesis System, Peptides, Radiohalogenation, Activity Recovery, Automatic Synthesis, Clinical Routine, Functionalized, One-Pot Synthesis, Prosthetic Groups, Radiochemical Purity, Radiochemical Yield, Solid-Phase Extraction, Amination, Projectiles, Purification, 4 Fluorobenzaldehyde F 18, Phenyl Group, Radioisotope, Unclassified Drug, Article, Chemical Labeling, Drug Purity, Drug Synthesis, Priority Journal, Radioactivity, Reactor, Solid Phase Extraction, Fluorine Radioisotopes, Isotope Labeling, Radiopharmaceuticals, Benzaldehydes Chemistry , Peptides Chemistry , Radiopharmaceuticals Chemistry,
Affiliations:
*** IBB - CNR ***
IBB-CNR, Edificio 10, Via Pansini 5, Napoli, Italy. antonio.speranza@hotmail.com
Dipartimento di Scienze Biomorfologiche e Funzionali, Università degli Studi di Napoli Federico II, Edificio 10, Via Pansini 5, Napoli, Italy
References:
Bergmann, R., Scheunemann, M., Heichert, C., Biodistribution and catabolism of 18F-labelled neurotensin (8-13) analogs (2002) Nucl. Med. Biol., 29, pp. 61-7
Berndt, M., Pietzsch, J., Wuest, F., Labeling of low-density lipoproteins using the 18F-labeled thiol-reactive reagent N-[6-(4-[18F]fluorobenzylidene)aminooxyhexyl]maleimide (2007) Nucl. Med. Biol., 34, pp. 5-15
Bruus-Jensen, K., Poethko, T., Schottelius, M., Hauser, A., Schwaiger, M., Wester, H.J., Chemoselective hydrazone formation between HYNIC-functionalized peptides and 18F-fluorinated aldehydes (2006) Nucl. Med. Biol., 33, pp. 173-183
Fredriksson, A., Ekberg, K., Ingvar, M., Johansson, B.L., Wahren, J., Stone-Elander, S., In vivo biodistribution and pharmacokinetics of 18F-labeled human C-peptide: evaluation in monkeys using positron emission tomography (2002) Life Sci., 71, pp. 1361-1370
Haubner, R., Wester, H.J., Weber, W.A., Noninvasive imaging of alpha(v)beta3 integrin expression using 18F-labeled RGD-containing glycopeptide and positron emission tomography (2001) Cancer Res., 61, pp. 1781-1785
Iwata, R., Pascali, C., Bogni, A., A new convenient method for the preparation of 4-[18F]fluorobenzylhalides (2000) Appl. Radiat. Isot., 52, pp. 87-92
Katounina, T., Besret, L., Dhilly, M., Petit-Tabouè, M.C., Barbelivien, A., Baron, J.C., Dauphin, F., Barrè, L., Synthesis and biological investigation of [18F]MR18445, a 5-HT3 receptor partial agonist (1998) Bioorg. Med. Chem., 6, pp. 789-795
Lee, Y.S., Jeong, J.M., Kim, H.W., Chang, Y.S., Kim, Y.J., Hong, M.K., Rai, G.B., Suh, Y.G., An improved method of 18F peptide labeling: hydrazone formation with HYNIC-conjugated c(RGDyK) (2006) Nucl. Med. Biol., 33, pp. 677-683
Lemaire, C., Damhaut, P., Plenevaux, A., Comar, D., Enantioselective synthesis of 6-[fluorine-18]-fluoro-l-dopa from no-carrier-added fluorine-18-fluoride (1997) J. Nucl. Med., 35, pp. 1996-2002
Mading, P., Fuchter, F., Wust, F., Module-assisted synthesis of the bifunctional labelling agent N-succinimidyl 4-[18F]fluorobenzoate ([18F]SFB) (2005) Appl. Radiat. Isot., 63, pp. 329-332
Marik, J., Sutcliffe, L.J., Fully automated preparation of n.c.a. 4-[18F]fluorobenzoic acid and N-succinimidyl 4-[18F]fluorobenzoate using a Siemens/CTI chemistry process control unit (CPCU) (2007) Appl. Radiat. Isot., 65, pp. 199-203
Okarvi, S.M., Recent progress in fluorine-18 labelled peptide radiopharmaceuticals (2001) Eur. J. Nucl. Med., 28, pp. 929-938
Schildan, A., Patt, M., Sabri, O., Synthesis procedure for routine production of 2-[18F]fluoro-3-(2(S)-azetidinylmethoxy)pyridine (2-[18F]F-A-85380) (2007) Appl. Radiat. Isot., 65, pp. 1244-1248
Stöcklin, G.L., Is there a future for clinical fluorine-18 radiopharmaceuticals (excluding FDG)? (1998) Eur. J. Nucl. Med., 25, pp. 1612-1616
Stöcklin, G., Wester, H.J., Strategies for radioligand development: Peptides for tumor targeting (1998) Positron Emission Tomography: A Critical Assessment of Recent Trends, pp. 57-90. , Gulyas, B, Müller-Gärtner, H.W, Eds, Kluwer Academic, Dordrecht, The Netherlands, pp
Toyokuni, T., Walsh, J.S., Dominguez, A., Phelps, M.E., Barrio, J.R., Gambhir, S.S., Satyamurthy, N., Synthesis of a new heterobifunctional linker, N-[4-(aminooxy)butyl]maleimide, for facile access to a thiol-reactive 18F-labeling agent (2003) Bioconjugate Chem., 14 (6), pp. 1253-1259
Lee, Y. S., Jeong, J. M., Kim, H. W., Chang, Y. S., Kim, Y. J., Hong, M. K., Rai, G. B., Suh, Y. G., An improved method of 18F peptide labeling: hydrazone formation with HYNIC-conjugated c (RGDyK) (2006) Nucl. Med. Biol., 33, pp. 677-683
Okarvi, S. M., Recent progress in fluorine-18 labelled peptide radiopharmaceuticals (2001) Eur. J. Nucl. Med., 28, pp. 929-938
St cklin, G. L., Is there a future for clinical fluorine-18 radiopharmaceuticals (excluding FDG)? (1998) Eur. J. Nucl. Med., 25, pp. 1612-1616
St cklin, G., Wester, H. J., Strategies for radioligand development: Peptides for tumor targeting (1998) Positron Emission Tomography: A Critical Assessment of Recent Trends, pp. 57-90. , Gulyas, B, M ller-G rtner, H. W, Eds, Kluwer Academic, Dordrecht, The Netherlands, pp
Fully automated synthesis procedure of 4-[18F]fluorobenzaldehyde by commercial synthesizer: amino-oxi peptide labelling prosthetic group
Automatic synthesis of 4-[18F]fluorobenzaldehyde has been developed by a commercially available TRACERlab™ FXF-N synthesis module to be used as prosthetic group for amino-oxy functionalized peptide labelling in clinical routine application. In addition a handmade purification device (HPD) has been setup to perform automatic cartridge purification as well as to back-up the reactor where one-pot synthesis is not applicable. Cartridges for solid phase extraction such as C18, C8, phenyl has been tested to best perform purification as well as activity recovery. Radiochemical yield (RCY) at end of synthesis (EOS) was in average 67% after about 45 min (90% decay corrected at EOB). The RCY of the entire procedure was 54% with a radiochemical purity above 99%. © 2009 Elsevier Ltd. All rights reserved.
Automatic synthesis of 4-[18F]fluorobenzaldehyde has been developed by a commercially available TRACERlab™ FXF-N synthesis module to be used as prosthetic group for amino-oxy functionalized peptide labelling in clinical routine application. In addition a handmade purification device (HPD) has been setup to perform automatic cartridge purification as well as to back-up the reactor where one-pot synthesis is not applicable. Cartridges for solid phase extraction such as C18, C8, phenyl has been tested to best perform purification as well as activity recovery. Radiochemical yield (RCY) at end of synthesis (EOS) was in average 67% after about 45 min (90% decay corrected at EOB). The RCY of the entire procedure was 54% with a radiochemical purity above 99%. © 2009 Elsevier Ltd. All rights reserved.
Fully automated synthesis procedure of 4-[18F]fluorobenzaldehyde by commercial synthesizer: amino-oxi peptide labelling prosthetic group
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