[en] Two new silicon-based prosthetic groups, derived from 3-[ethoxybis(1-methylethyl)silyl]propanamine, have been prepd.
in good yields. These silicon groups bearing an acid or an azide group were coupled to a model tripeptide (Leu-Gly-
Gly) either through a classical amide bond formation or through "click chem." via the Huisgen cycloaddn. The
radiolabeling with fluorine-18 by substitution of the ethoxy group at silicon has been carried out with success in 51-54%
decay cor. radiochem. yields. Radiolabeled peptides were easily prepd. by direct 18F-fluorination of the silicon-bearing
tripeptide or by coupling the peptide with a radiolabeled silicon-based prosthetic group. Their stabilities in physiol.
medium were studied and proved poor.
Disciplines :
Chemistry
Author, co-author :
Balentova, Eva
Collet, Charlotte
Lamande-Langle, Sandrine
Chretien, Françoise
Thonon, David ; Université de Liège - ULiège > Centre de recherches du cyclotron
Aerts, Joël ; Université de Liège - ULiège > Centre de recherches du cyclotron
Lemaire, Christian ; Université de Liège - ULiège > Centre de recherches du cyclotron
Luxen, André ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie organique de synthèse
Chapleur, Yves
Language :
English
Title :
Synthesis and hydrolytic stability of novel 3-[18F]fluoroethoxybis(1-methylethyl)silyl]propanamine-based prosthetic groups
(b) C. Wängler, R. Schirrmacher, P. Bartenstein, B. Wängler, Curr. Med. Chem. 17 (2010) 1092-1116.
(a) P. Mäding, F. Füchtner, F. Wüst, Appl. Radiat. Isot. 63 (2005) 329-332;
(b) K.J. Guenther, S. Yoganathan, R. Garofalo, T. Kawabata, T. Strack, R. Labiris, M. Dolovich, R. Chirakal, J.F. Valliant, J. Med. Chem. 49 (2006) 1466-1474;
(c) J. Toretsky, A. Levenson, I.N. Weinberg, J.F. Tait, A. Uren, R.C. Mease, Nucl. Med. Biol. 31 (2004) 747-752.
(a) B. De Bruin, B. Kuhnast, F. Hinnen, L. Yaouancq, M. Amessou, L. Johannes, A. Samson, R. Boisgard, B. Tavitian, F. Dolle, Bioconjug. Chem. 16 (2005) 406-420;
(b) M. Glaser, H. Karlsen, M. Solbakken, J. Arukwe, F. Brady, S.K. Luthra, A. Cuthbertson, Bioconjug. Chem. 15 (2004) 1447-1453;
(c) M. Berndt, J. Pietzsch, F. Wuest, Nucl. Med. Biol. 34 (2007) 5-15.
(a) K. Bruus-Jensen, T. Poethko, M. Schottelius, A. Hauser, M. Schwaiger, H.J. Wester, Nucl. Med. Biol. 33 (2006) 173-183;
(c) T. Poethko, M. Schottelius, G. Thumshirn, U. Hersel, M. Herz, G. Henriksen, H. Kessler, M. Schwaiger, H.J. Wester, J. Nucl. Med. 45 (2004) 892-902;
(d) G. Thumshirn, S.L. Hersel, H. Goodman, H. Kessler, Chem. Eur. J. 9 (2003) 2717-2725.
(a) L. Carroll, S. Boldon, R. Bejot, J.E. Moore, J. Declerck, V. Gouverneur, Org. Biomol. Chem. 9 (2011) 136-140;
(b) V. Gouverneur, R. Bejot, L. Carroll, S. Boldon, PCT Int Appl WO 2010133851, 140 pp.
(c) M. Pretze, F. Wuest, T. Peppel, M. Koeckerling, C. Mamat, Tetrahedron Lett. 51 (2010) 6410-6414;
(d) A. Gaeta, J. Woodcraft, S. Plant, J. Goggi, P. Jones, M. Battle, W. Trigg, S.K. Luthra, M. Glaser, Bioorg. Med. Chem. Lett. 20 (2010) 4649-4652;
(e) M.S. Robillard, H. Gruell, PCT Int Appl WO 2006038185, 59 pp..
(a) J. Marik, J.L. Sutcliffe, Tetrahedron Lett. 47 (2006) 6681-6684;
(b) D. Thonon, C. Kech, J. Paris, C. Lemaire, A. Luxen, Bioconjug. Chem. 20 (2009) 817-823;
(c) M. Glaser, G. Robins, J. Label Compd. Radiopharm. 52 (2009) 407-414 (And references cited herein).
(a) E. Schirrmacher, B. Wängler, M. Cypryk, G. Bradtmöller, M. Schäfer, M. Eisenhut, K. Jurkschat, R. Schirrmacher, Bioconjug. Chem. 18 (2007) 2085-2089;
(b) B. Wängler, G. Quandt, L. Oivkova, E. Schirrmacher, C. Wängler, G. Boening, M. Hacker, M. Schmoeckel, K. Jurkschat, P. Bartenstein, R. Schirrmacher, Bioconjug. Chem. 20 (2009) 317-321;
(c) J.C. Walsh, K.M. Akhoon, N. Satyamurthy, J.R. Barrio, M.E. Phelps, S.S. Gambhir, T. Toyokuni, J. Label Compd. Radiopharm. 42 (1999) S1-S3;
(d) U. Choudhry, K. Martin, D. Malnard, S.C.G. Biagini, P.J. Blower, Eur. J. Nucl. Med. Mol. Imaging 33 (2006) S306;
(e) U. Choudhry, R. Paul, P. Blower, S. Biagini, Eur. J. Nucl. Med. Mol. Imaging 34 (2007) S332;
(f) U. Choudhry, K.E. Martin, S. Biagini, P.J. Blower, Nucl. Med. Commun. 27 (2006) 293.
(a) R. Schirrmacher, G. Bradtmöller, E. Schirrmacher, O. Thews, J. Tillmanns, P. Siessmeier, H.G. Buchholz, P. Bartenstein, B. Wängler, C.M. Niemeyer, K. Jurkschat, Angew. Chem., Int. Ed. 45 (2006) 6047-6050;
(b) A. Höhne, L. Yu, L. Mu, M. Reiher, U. Voigtmann, U. Klar, K. Graham, P.A. Schubiger, S.M. Ametamey, Chem. Eur. J. 15 (2009) 3736-3743;
(c) A. Srinivasan, L. Lehmann, U. Voigtmann, T. Stellfels, S.M. Ametamey, U. Klar, et al., PCT Int Appl WO 2008040441, 155 pp.
(d) L. Mu, A. Höhne, P.A. Schubiger, S.M. Ametaney, K. Graham, J.E. Cyr, L. Dinkelborg, T. Stellfeld, A. Srinivasan, U. Voigtmann, U. Klar, Angew. Chem., Int. Ed. 47 (2008) 4922-4925;
(e) A. Höhne, L. Mu, M. Honer, P.A. Schubiger, S.M. Ametaney, K. Graham, T. Stellfeld, S. Borkowski, D. Berndorff, U. Klar, U. Voigtmann, J.E. Cyr, M. Friebe, L. Dinkelborg, A. Srinivasan, Bioconjug. Chem. 19 (2008) 1871-1879.
R. Ting, M.J. Adams, T.J. Ruth, D.M. Perrin, J. Am. Chem. Soc. 127 (2005) 13094-13095.
C. Granjean, A. Boutonnier, C. Guerreiro, J.-M. Fournier, L.A. Mulard, J. Org. Chem. 70 (2005) 7123-7132.
J. Aerts, S. Voccia, C. Lemaire, F. Giacomelli, D. Goblet, D. Thonon, A. Plenevaux, G. Warnock, A. Luxen, Tetrahedron Lett. 51 (2010) 64-66.
P. Bohn, A. Deyine, R. Azzouz, L. Bailly, C. Fiol-Petit, L. Bischoff, C. Fruit, F. Marsais, P. Vera, Nucl. Med. Biol. 36 (2009) 895-905.
