Synthetic Strategy to Prepare DOTA-Based Bifunctional Chelating Agent Ready to Bind Biomolecular Probes (297 visite)
Int J Pept Res Ther (ISSN: 1573-3149, 0929-5666), 2013 Sep; 19(3): 199-202.
Tipo di articolo: Journal Article,
Impact factor: 0.825, Impact factor a 5 anni: 0.937
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84887442981&partnerID=40&md5=6c4df52ecbe240037dcf1cc52e9f556f
Parole chiave: Bifunctional Chelating Agent, Biological Probe, Dota, Peptide Labeling, 10 Tetraazacyclododecane 1, 7 Tris(acetic Acid) 10 Butyrate Mono(n Hydroxysuccinimidyl Ester), Immunoglobulin F(ab) Fragment, Tetraxetan, Unclassified Drug, Amino Acid Sequence, Article, Chemical Labeling, Chemical Reaction, Drug Synthesis, High Performance Liquid Chromatography, Molecular Probe, Physical Chemistry, Protein Binding, Proton Nuclear Magnetic Resonance, Reaction Analysis, 7 Tris (acetic Acid) 10 Butyrate Mono (n Hydroxysuccinimidyl Ester), Immunoglobulin F (ab) Fragment,
Affiliazioni:
*** IBB - CNR ***
Institute of Biostructure and Bioimaging, National Research Council, Via Mezzocannone 16, 80138 Naples, Italy
Riferimenti:
Barge, A., Cappelletti, E., Cravotto, G., Ferrigato, A., Lattuada, L., Marinoni, F., Tei, L., Synthesis of functionalised HP-DO3A chelating agents for conjugation to biomolecules (2009) Org Biomol Chem, 7, pp. 3810-3816. , 19707687 10.1039/b905369g 1:CAS:528:DC%2BD1MXhtVGgsLr
Bernhard, C., Moreau, M., Lhenry, D., Goze, C., Boschetti, F., Rousselin, Y., Brunotte, F., Denat, F., DOTAGA-anhydride: A valuable building block for the preparation of DOTA-like chelating agents (2012) Chem Eur J, 18, pp. 7834-7841. , 22615050 10.1002/chem.201200132 1:CAS:528:DC%2BC38XntlWgtbg%3D
Dischino, D.D., Delaney, E.J., Emswiller, J.E., Gaughan, G.T., Prasad, J.S., Srivastava, S.K., Tweedle, M.F., Synthesis of nonionic gadolinium chelates useful as contrast agents for magnetic resonance imaging: 1,4,7-tris(carboxymethyl)-10-substituted-1,4,7,10- tetraazacyclododecanes and their corresponding gadolinium chelates (1991) Inorg Chem, 30, pp. 1265-1269. , 10.1021/ic00006a020 1:CAS:528:DyaK3MXhslOitro%3D
Jamous, M., Haberkorn, U., Mier, W., DOTA-tris(OPp ester) as a bifunctional prochelator for the preparation of DOTA-peptide conjugates (2012) Tetrahedron Lett, 53, pp. 6810-6814. , 10.1016/j.tetlet.2012.10.007 1:CAS:528:DC%2BC38XhsFynu7nK
Kaiser, E., Colescott, R.L., Bossinger, C.D., Cook, P.I., Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides (1970) Anal Biochem, 34, pp. 595-598. , 5443684 10.1016/0003-2697(70)90146-6 1:CAS:528:DyaE3cXhtVWjur0%3D
Knor, S., Modlinger, A., Poethko, T., Schottelius, M., Wester, H.J., Kessler, H., Synthesis of novel 1,4,7,10-tetraazacyclodecane-1,4,7,10-tetraacetic acid (DOTA) derivatives for chemoselective attachment to unprotected polyfunctionalized compounds (2007) Chem Eur J, 13, pp. 6082-6090. , 17503419 10.1002/chem.200700231
Lattuada, L., Barge, A., Cravotto, G., Giovenzana, G.B., Tei, L., The synthesis and application of polyamino polycarboxylic bifunctional chelating agents (2011) Chem Soc Rev, 40, pp. 3019-3049. , 21384039 10.1039/c0cs00199f 1:CAS:528:DC%2BC3MXkvVWisrw%3D
Li, C., Winnard, Jr.P., Bhujwalla, Z.M., Facile synthesis of 1-(acetic acid)-4,7,10-tris(tert- butoxycarbonylmethyl)-1,4,7,10-tetraaza-cyclododecane: A reactive precursor chelating agent (2009) Tetrahedron Lett, 50, pp. 2929-2931. , 20161259 10.1016/j.tetlet.2009.03.198 1:CAS:528:DC%2BD1MXltl2msLs%3D
Mier, W., Hoffend, J., Kramer, S., Schuhmacher, J., Hull, W.E., Eisenhut, M., Haberkorn, U., Conjugation of DOTA using isolated phenolic active esters: Labeling and biodistribution of albumin as blood pool marker (2005) Bioconjugate Chem, 16, pp. 237-240. , 10.1021/bc034216c 1:CAS:528:DC%2BD2cXhtVCmsbrL
Mishra, A.K., Chatal, J.F., Synthesis of macrocyclic bifunctional chelating agents: 1,4,7-tris(carboxymethyl)-10-(2-aminoethyl)-1,4,7,10-tetraazacyclododecane and 1,4,8-tris(carboxymethyl)-11-(2-aminoethyl)-1,4,8,11-tetraazacyclotetradecane (2001) New J Chem, 25, pp. 336-339. , 10.1039/b006978g 1:CAS:528:DC%2BD3MXosFajtQ%3D%3D
Mishra, A., Pfeuffer, J., Mishra, R., Engelmann, J., Mishra, A.K., Ugurbil, K., Logothetis, N.K., A new class of Gd-based DO3A-ethylamine-derived targeted contrast agents for MR and optical imaging (2006) Bioconjugate Chem, 17, pp. 773-780. , 10.1021/bc050295b 1:CAS:528:DC%2BD28XjvVSnsLk%3D
Wangler, C., Wangler, B., Eisenhut, M., Haberkorn, U., Mier, W., Improved syntheses and applicability of different DOTA building blocks for multiply derivatized scaffolds (2008) Bioorg Med Chem, 16, pp. 2606-2616. , 18065226 10.1016/j.bmc.2007.11.044 1:STN:280:DC%2BD1c7otFOrtA%3D%3D
Yoo, B., Pagel, M.D., A facile synthesis of α-amino-DOTA as a versatile molecular imaging probe (2006) Tetrahedron Lett, 47, pp. 7327-7330. , 10.1016/j.tetlet.2006.08.019 1:CAS:528:DC%2BD28XptlCku78%3D
Dischino, D. D., Delaney, E. J., Emswiller, J. E., Gaughan, G. T., Prasad, J. S., Srivastava, S. K., Tweedle, M. F., Synthesis of nonionic gadolinium chelates useful as contrast agents for magnetic resonance imaging: 1, 4, 7-tris (carboxymethyl) -10-substituted-1, 4, 7, 10- tetraazacyclododecanes and their corresponding gadolinium chelates (1991) Inorg Chem, 30, pp. 1265-1269. , 10. 1021/ic00006a020 1: CAS: 528: DyaK3MXhslOitro%3D
Mishra, A. K., Chatal, J. F., Synthesis of macrocyclic bifunctional chelating agents: 1, 4, 7-tris (carboxymethyl) -10- (2-aminoethyl) -1, 4, 7, 10-tetraazacyclododecane and 1, 4, 8-tris (carboxymethyl) -11- (2-aminoethyl) -1, 4, 8, 11-tetraazacyclotetradecane (2001) New J Chem, 25, pp. 336-339. , 10. 1039/b006978g 1: CAS: 528: DC%2BD3MXosFajtQ%3D%3D
Yoo, B., Pagel, M. D., A facile synthesis of -amino-DOTA as a versatile molecular imaging probe (2006) Tetrahedron Lett, 47, pp. 7327-7330. , 10. 1016/j. tetlet. 2006. 08. 019 1: CAS: 528: DC%2BD28XptlCku78%3D
Int J Pept Res Ther (ISSN: 1573-3149, 0929-5666), 2013 Sep; 19(3): 199-202.
Tipo di articolo: Journal Article,
Impact factor: 0.825, Impact factor a 5 anni: 0.937
Url: http://www.scopus.com/inward/record.url?eid=2-s2.0-84887442981&partnerID=40&md5=6c4df52ecbe240037dcf1cc52e9f556f
Parole chiave: Bifunctional Chelating Agent, Biological Probe, Dota, Peptide Labeling, 10 Tetraazacyclododecane 1, 7 Tris(acetic Acid) 10 Butyrate Mono(n Hydroxysuccinimidyl Ester), Immunoglobulin F(ab) Fragment, Tetraxetan, Unclassified Drug, Amino Acid Sequence, Article, Chemical Labeling, Chemical Reaction, Drug Synthesis, High Performance Liquid Chromatography, Molecular Probe, Physical Chemistry, Protein Binding, Proton Nuclear Magnetic Resonance, Reaction Analysis, 7 Tris (acetic Acid) 10 Butyrate Mono (n Hydroxysuccinimidyl Ester), Immunoglobulin F (ab) Fragment,
Affiliazioni:
*** IBB - CNR ***
Institute of Biostructure and Bioimaging, National Research Council, Via Mezzocannone 16, 80138 Naples, Italy
Riferimenti:
Barge, A., Cappelletti, E., Cravotto, G., Ferrigato, A., Lattuada, L., Marinoni, F., Tei, L., Synthesis of functionalised HP-DO3A chelating agents for conjugation to biomolecules (2009) Org Biomol Chem, 7, pp. 3810-3816. , 19707687 10.1039/b905369g 1:CAS:528:DC%2BD1MXhtVGgsLr
Bernhard, C., Moreau, M., Lhenry, D., Goze, C., Boschetti, F., Rousselin, Y., Brunotte, F., Denat, F., DOTAGA-anhydride: A valuable building block for the preparation of DOTA-like chelating agents (2012) Chem Eur J, 18, pp. 7834-7841. , 22615050 10.1002/chem.201200132 1:CAS:528:DC%2BC38XntlWgtbg%3D
Dischino, D.D., Delaney, E.J., Emswiller, J.E., Gaughan, G.T., Prasad, J.S., Srivastava, S.K., Tweedle, M.F., Synthesis of nonionic gadolinium chelates useful as contrast agents for magnetic resonance imaging: 1,4,7-tris(carboxymethyl)-10-substituted-1,4,7,10- tetraazacyclododecanes and their corresponding gadolinium chelates (1991) Inorg Chem, 30, pp. 1265-1269. , 10.1021/ic00006a020 1:CAS:528:DyaK3MXhslOitro%3D
Jamous, M., Haberkorn, U., Mier, W., DOTA-tris(OPp ester) as a bifunctional prochelator for the preparation of DOTA-peptide conjugates (2012) Tetrahedron Lett, 53, pp. 6810-6814. , 10.1016/j.tetlet.2012.10.007 1:CAS:528:DC%2BC38XhsFynu7nK
Kaiser, E., Colescott, R.L., Bossinger, C.D., Cook, P.I., Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides (1970) Anal Biochem, 34, pp. 595-598. , 5443684 10.1016/0003-2697(70)90146-6 1:CAS:528:DyaE3cXhtVWjur0%3D
Knor, S., Modlinger, A., Poethko, T., Schottelius, M., Wester, H.J., Kessler, H., Synthesis of novel 1,4,7,10-tetraazacyclodecane-1,4,7,10-tetraacetic acid (DOTA) derivatives for chemoselective attachment to unprotected polyfunctionalized compounds (2007) Chem Eur J, 13, pp. 6082-6090. , 17503419 10.1002/chem.200700231
Lattuada, L., Barge, A., Cravotto, G., Giovenzana, G.B., Tei, L., The synthesis and application of polyamino polycarboxylic bifunctional chelating agents (2011) Chem Soc Rev, 40, pp. 3019-3049. , 21384039 10.1039/c0cs00199f 1:CAS:528:DC%2BC3MXkvVWisrw%3D
Li, C., Winnard, Jr.P., Bhujwalla, Z.M., Facile synthesis of 1-(acetic acid)-4,7,10-tris(tert- butoxycarbonylmethyl)-1,4,7,10-tetraaza-cyclododecane: A reactive precursor chelating agent (2009) Tetrahedron Lett, 50, pp. 2929-2931. , 20161259 10.1016/j.tetlet.2009.03.198 1:CAS:528:DC%2BD1MXltl2msLs%3D
Mier, W., Hoffend, J., Kramer, S., Schuhmacher, J., Hull, W.E., Eisenhut, M., Haberkorn, U., Conjugation of DOTA using isolated phenolic active esters: Labeling and biodistribution of albumin as blood pool marker (2005) Bioconjugate Chem, 16, pp. 237-240. , 10.1021/bc034216c 1:CAS:528:DC%2BD2cXhtVCmsbrL
Mishra, A.K., Chatal, J.F., Synthesis of macrocyclic bifunctional chelating agents: 1,4,7-tris(carboxymethyl)-10-(2-aminoethyl)-1,4,7,10-tetraazacyclododecane and 1,4,8-tris(carboxymethyl)-11-(2-aminoethyl)-1,4,8,11-tetraazacyclotetradecane (2001) New J Chem, 25, pp. 336-339. , 10.1039/b006978g 1:CAS:528:DC%2BD3MXosFajtQ%3D%3D
Mishra, A., Pfeuffer, J., Mishra, R., Engelmann, J., Mishra, A.K., Ugurbil, K., Logothetis, N.K., A new class of Gd-based DO3A-ethylamine-derived targeted contrast agents for MR and optical imaging (2006) Bioconjugate Chem, 17, pp. 773-780. , 10.1021/bc050295b 1:CAS:528:DC%2BD28XjvVSnsLk%3D
Wangler, C., Wangler, B., Eisenhut, M., Haberkorn, U., Mier, W., Improved syntheses and applicability of different DOTA building blocks for multiply derivatized scaffolds (2008) Bioorg Med Chem, 16, pp. 2606-2616. , 18065226 10.1016/j.bmc.2007.11.044 1:STN:280:DC%2BD1c7otFOrtA%3D%3D
Yoo, B., Pagel, M.D., A facile synthesis of α-amino-DOTA as a versatile molecular imaging probe (2006) Tetrahedron Lett, 47, pp. 7327-7330. , 10.1016/j.tetlet.2006.08.019 1:CAS:528:DC%2BD28XptlCku78%3D
Dischino, D. D., Delaney, E. J., Emswiller, J. E., Gaughan, G. T., Prasad, J. S., Srivastava, S. K., Tweedle, M. F., Synthesis of nonionic gadolinium chelates useful as contrast agents for magnetic resonance imaging: 1, 4, 7-tris (carboxymethyl) -10-substituted-1, 4, 7, 10- tetraazacyclododecanes and their corresponding gadolinium chelates (1991) Inorg Chem, 30, pp. 1265-1269. , 10. 1021/ic00006a020 1: CAS: 528: DyaK3MXhslOitro%3D
Mishra, A. K., Chatal, J. F., Synthesis of macrocyclic bifunctional chelating agents: 1, 4, 7-tris (carboxymethyl) -10- (2-aminoethyl) -1, 4, 7, 10-tetraazacyclododecane and 1, 4, 8-tris (carboxymethyl) -11- (2-aminoethyl) -1, 4, 8, 11-tetraazacyclotetradecane (2001) New J Chem, 25, pp. 336-339. , 10. 1039/b006978g 1: CAS: 528: DC%2BD3MXosFajtQ%3D%3D
Yoo, B., Pagel, M. D., A facile synthesis of -amino-DOTA as a versatile molecular imaging probe (2006) Tetrahedron Lett, 47, pp. 7327-7330. , 10. 1016/j. tetlet. 2006. 08. 019 1: CAS: 528: DC%2BD28XptlCku78%3D
Due to the continued interest in new bifunctional chelating agents (BFCA), we focused on the development of a convenient synthesis of 1,4,7,10- tetraazacyclododecane-1,4,7-tris(acetic acid)-10-butyrate mono (N-hydroxysuccinimidyl ester). It consists in the macrocycle DO3A derivatized with an aliphatic linker containing an active ester that requires selective and mild conditions to react with the targeting biomolecule. It is important to underlay the versatility of the obtained BFCA, which can be conjugated both to a biomolecule (protein, Fab fragment) or to a synthetic molecule. In a subsequent step, the developed chelator was successfully conjugated to a peptide sequence. © 2013 Springer Science+Business Media New York.
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