ACS Publications. Most Trusted. Most Cited. Most Read

OR SEARCH CITATIONS

My Activity
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:Bioconjugate Chem. 1999, 10, 1, 137-140
RETURN TO ISSUEPREVTechnical NoteNEXT

l-Glutamic Acid and l-Lysine as Useful Building Blocks for the Preparation of Bifunctional DTPA-like Ligands†

View Author Information
Bracco spa, Milano Research Centre, via E. Folli 50, 20134 Milano, Italy
Cite this: Bioconjugate Chem. 1999, 10, 1, 137–140
Publication Date (Web):December 31, 1998
https://doi.org/10.1021/bc970212u
Copyright © 1999 American Chemical Society
Request reuse permissions

    Article Views

    1119

    Altmetric

    -

    Citations

    72
    LEARN ABOUT THESE METRICS
    Read OnlinePDF (91 KB)
    Get e-Alerts
    SUBJECTS:

    Abstract

    Bisalkylation of suitably protected l-glutamic acid and l-lysine derivatives with tert-butyl N-(2-bromoethyl)iminodiacetate 2, followed by deprotection of the ω functional group affords N,N-bis[2-[bis[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]ethyl]-l-glutamic acid 1-(1,1-dimethylethyl) ester 4 and N2,N2-bis[2-[bis[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]ethyl]-l-lysine 1,1-dimethylethyl ester 7. Such compounds feature a carboxylic or an amino group, respectively, which are available for conjugation with a suitable partner via formation of an amide bond. The conjugates, which can be prepared in this way, contain a chelating subunit in which all five acetic residues of DTPA are available for the complexation of metal ions. Direct bisalkylation of glycine with 2 promptly gives N,N-bis[2-[bis[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]ethyl]glycine 11. The latter allows to achieve conjugates in which the central acetic group of DTPA is selectively converted into an acetamide.

    †

     Presented in part at the 35th National Organic Chemistry Symposium, San Antonio, TX, June 1997.

    *

     To whom correspondence should be addressed. Phone:  +39 02 21772353. Fax:  +39 02 26410678.

    Cited By

    This article is cited by 72 publications.

    1. Ding-Kun Ji, Giacomo Reina, Hanyu Liang, Da Zhang, Shi Guo, Belén Ballesteros, Cécilia Ménard-Moyon, Juan Li, Alberto Bianco. Gadolinium-Incorporated Carbon Nanodots for T1-Weighted Magnetic Resonance Imaging. ACS Applied Nano Materials 2021, 4 (2) , 1467-1477. https://doi.org/10.1021/acsanm.0c02993
    2. Marianne Liebi, Simon Kuster, Joachim Kohlbrecher, Takashi Ishikawa, Peter Fischer, Peter Walde, and Erich J. Windhab . Cholesterol-Diethylenetriaminepentaacetate Complexed with Thulium Ions Integrated into Bicelles To Increase Their Magnetic Alignability. The Journal of Physical Chemistry B 2013, 117 (47) , 14743-14748. https://doi.org/10.1021/jp406599c
    3. Sarah El Habnouni, Benjamin Nottelet, Vincent Darcos, Barbara Porsio, Laurent Lemaire, Florence Franconi, Xavier Garric, and Jean Coudane . MRI-Visible Poly(ε-caprolactone) with Controlled Contrast Agent Ratios for Enhanced Visualization in Temporary Imaging Applications. Biomacromolecules 2013, 14 (10) , 3626-3634. https://doi.org/10.1021/bm400978a
    4. Giuseppe Digilio, Valeria Menchise, Eliana Gianolio, Valeria Catanzaro, Carla Carrera, Roberta Napolitano, Franco Fedeli and Silvio Aime . Exofacial Protein Thiols as a Route for the Internalization of Gd(III)-Based Complexes for Magnetic Resonance Imaging Cell Labeling. Journal of Medicinal Chemistry 2010, 53 (13) , 4877-4890. https://doi.org/10.1021/jm901876r
    5. Pier Lucio Anelli, Marino Brocchetta, Luciano Lattuada, Giuseppe Manfredi, Pierfrancesco Morosini, Marcella Murru, Daniela Palano, Marco Sipioni and Massimo Visigalli. Scale-Up of Trisodium [(3β,5β,12α)-3-[[4(S)-4-[Bis[2-[bis[(carboxy-kO)methyl]amino-kN]ethyl]amino-kN]-4-(carboxy-kO)-1-oxobutyl]amino]-12-hydroxycholan-24-oato(6-)]gadolinate(3-)], a Gd(III) Complex under Development As a Contrast Agent for MRI Coronary Angiography. Organic Process Research & Development 2009, 13 (4) , 739-746. https://doi.org/10.1021/op900008a
    6. Mauro Vaccaro,, Antonella Accardo,, Diego Tesauro,, Gaetano Mangiapia,, David Löf,, Karin Schillén,, Olle Söderman,, Giancarlo Morelli, and, Luigi Paduano. Supramolecular Aggregates of Amphiphilic Gadolinium Complexes as Blood Pool MRI/MRA Contrast Agents:  Physicochemical Characterization. Langmuir 2006, 22 (15) , 6635-6643. https://doi.org/10.1021/la053500k
    7. Antonella Accardo,, Diego Tesauro,, Paola Roscigno,, Eliana Gianolio,, Luigi Paduano,, Gerardino D'Errico,, Carlo Pedone, and, Giancarlo Morelli. Physicochemical Properties of Mixed Micellar Aggregates Containing CCK Peptides and Gd Complexes Designed as Tumor Specific Contrast Agents in MRI. Journal of the American Chemical Society 2004, 126 (10) , 3097-3107. https://doi.org/10.1021/ja039195b
    8. I. Fraser Pickersgill and, Henry Rapoport. Preparation of Functionalized, Conformationally Constrained DTPA Analogues from l- or d-Serine and trans-4-Hydroxy-l-proline. Hydroxymethyl Substituents on the Central Acetic Acid and on the Backbone. The Journal of Organic Chemistry 2000, 65 (13) , 4048-4057. https://doi.org/10.1021/jo000071g
    9. Samuel Achilefu,, R. Randy Wilhelm,, Hermo N. Jimenez,, Michelle A. Schmidt, and, Ananth Srinivasan. A New Method for the Synthesis of Tri-tert-butyl Diethylenetriaminepentaacetic Acid and Its Derivatives. The Journal of Organic Chemistry 2000, 65 (5) , 1562-1565. https://doi.org/10.1021/jo991453t
    10. Bin Wei, Na Weng, Lei Fu, Yuxuan Li, Xu Wang, Ruijuan Yin, Tao Jiang. Synthesis and bioactivity evaluation of a myelin-specific contrast agent for magnetic resonance imaging of myelination in central nervous system. Bioorganic & Medicinal Chemistry 2023, 84 , 117257. https://doi.org/10.1016/j.bmc.2023.117257
    11. Jongeun Kang, Eunha Hwang, Hyunseung Lee, Mi Young Cho, Sanu Karan, Hak Nam Kim, Jong Seung Kim, Jonathan L. Sessler, Sankarprasad Bhuniya, Kwan Soo Hong. An Activatable T1-Weighted MR Contrast Agent: A Noninvasive Tool for Tracking the Vicinal Thiol Motif of Thioredoxin in Live Cells. Molecules 2021, 26 (7) , 2018. https://doi.org/10.3390/molecules26072018
    12. Silvio Aime, Fabio Travagin, Enzo Terreno, Giovanni B. Giovenzana. Chemistry of Molecular Imaging: An Overview. 2021, 423-443. https://doi.org/10.1016/B978-0-12-816386-3.00029-6
    13. Kenji Mishiro, Hirofumi Hanaoka, Aiko Yamaguchi, Kazuma Ogawa. Radiotheranostics with radiolanthanides: Design, development strategies, and medical applications. Coordination Chemistry Reviews 2019, 383 , 104-131. https://doi.org/10.1016/j.ccr.2018.12.005
    14. Giovanni B. Giovenzana, Luciano Lattuada, Roberto Negri. Recent Advances in Bifunctional Paramagnetic Chelates for MRI. Israel Journal of Chemistry 2017, 57 (9) , 825-832. https://doi.org/10.1002/ijch.201700028
    15. Ali Mohamadi, Lawrence W. Miller. Efficient route to pre-organized and linear polyaminopolycarboxylates: Cy-TTHA, Cy-DTPA and mono/di- reactive, tert -butyl protected TTHA/Cy-TTHA. Tetrahedron Letters 2017, 58 (15) , 1441-1444. https://doi.org/10.1016/j.tetlet.2017.02.056
    16. Stéphane Isabettini, Sarah Massabni, Arnel Hodzic, Dzana Durovic, Joachim Kohlbrecher, Takashi Ishikawa, Peter Fischer, Erich J. Windhab, Peter Walde, Simon Kuster. Molecular engineering of lanthanide ion chelating phospholipids generating assemblies with a switched magnetic susceptibility. Physical Chemistry Chemical Physics 2017, 19 (31) , 20991-21002. https://doi.org/10.1039/C7CP03994H
    17. CuhaWijay Sathiyajith, Andrew J. Hallett, Angelo J. Amoroso, Peter G. Edwards. Dual modal imaging agents based on chromophore-bearing DTPA analogues. RSC Advances 2017, 7 (61) , 38463-38470. https://doi.org/10.1039/C7RA06946D
    18. L. Chaabane, L. Tei, L. Miragoli, L. Lattuada, M. von Wronski, F. Uggeri, V. Lorusso, S. Aime. In Vivo MR Imaging of Fibrin in a Neuroblastoma Tumor Model by Means of a Targeting Gd-Containing Peptide. Molecular Imaging and Biology 2015, 17 (6) , 819-828. https://doi.org/10.1007/s11307-015-0846-4
    19. Lorenzo Tei, Alessandro Barge, Matteo Galli, Roberta Pinalli, Luciano Lattuada, Eliana Gianolio, Silvio Aime. Polyhydroxylated GdDTPA-derivatives as high relaxivity magnetic resonance imaging contrast agents. RSC Advances 2015, 5 (91) , 74734-74743. https://doi.org/10.1039/C5RA15071J
    20. Iris Marangon, Cécilia Ménard‐Moyon, Jelena Kolosnjaj‐Tabi, Marie Lys Béoutis, Lénaic Lartigue, Damien Alloyeau, Elzbieta Pach, Belén Ballesteros, Gwennhael Autret, Tsedev Ninjbadgar, Dermot F. Brougham, Alberto Bianco, Florence Gazeau. Covalent Functionalization of Multi‐walled Carbon Nanotubes with a Gadolinium Chelate for Efficient T 1 ‐Weighted Magnetic Resonance Imaging. Advanced Functional Materials 2014, 24 (45) , 7173-7186. https://doi.org/10.1002/adfm.201402234
    21. Prakash Sista, Koushik Ghosh, Jennifer S. Martinez, Reginaldo C. Rocha. Metallo-Biopolymers: Conjugation Strategies and Applications. Polymer Reviews 2014, 54 (4) , 627-676. https://doi.org/10.1080/15583724.2014.913063
    22. Giovanni B. Giovenzana, Claudia Guanci, Silvia Demattio, Luciano Lattuada, Veronica Vincenzi. Synthesis of bifunctional chelating agents based on mono and diphosphonic derivatives of diethylenetriaminepentaacetic acid. Tetrahedron 2014, 70 (32) , 4809-4813. https://doi.org/10.1016/j.tet.2014.05.030
    23. Edyta Mikuła, Magdalena Sulima, Ilona Marszałek, Aleksandra Wysłouch-Cieszyńska, Peter Verwilst, Wim Dehaen, Jerzy Radecki, Hanna Radecka. Oriented Immobilization of His-Tagged Protein on a Redox Active Thiol Derivative of DPTA-Cu(II) Layer Deposited on a Gold Electrode—The Base of Electrochemical Biosensors. Sensors 2013, 13 (9) , 11586-11602. https://doi.org/10.3390/s130911586
    24. Jan Kotek, Vojtěch Kubíček, Petr Hermann, Ivan Lukeš. Synthesis and Characterization of Ligands and their Gadolinium(III) Complexes. 2013, 83-155. https://doi.org/10.1002/9781118503652.ch3
    25. Leonardo Manzoni, Laura Belvisi, Daniela Arosio, Maria Paola Bartolomeo, Aldo Bianchi, Chiara Brioschi, Federica Buonsanti, Claudia Cabella, Cesare Casagrande, Monica Civera, Marilenia De Matteo, Lorenza Fugazza, Luciano Lattuada, Federico Maisano, Luigi Miragoli, Cristina Neira, Michael Pilkington‐Miksa, Carlo Scolastico. Synthesis of Gd and 68 Ga Complexes in Conjugation with a Conformationally Optimized RGD Sequence as Potential MRI and PET Tumor‐Imaging Probes. ChemMedChem 2012, 7 (6) , 1084-1093. https://doi.org/10.1002/cmdc.201200043
    26. Oren Giladi, Simon Benita. Immunonanoparticles for Nuclear Imaging and Radiotherapy. 2012, 427-456. https://doi.org/10.1002/9781118229019.ch21
    27. Geert Dehaen, Svetlana V. Eliseeva, Kristof Kimpe, Sophie Laurent, Luce Vander Elst, Robert N. Muller, Wim Dehaen, Koen Binnemans, Tatjana N. Parac‐Vogt. A Self‐Assembled Complex with a Titanium(IV) Catecholate Core as a Potential Bimodal Contrast Agent. Chemistry – A European Journal 2012, 18 (1) , 293-302. https://doi.org/10.1002/chem.201101413
    28. Jin‐Hwan Kim, Jae‐Cheong Lim, Ki‐Cheol Yun, Sun‐Ju Choi, Young‐Don Hong. Preparation and preliminary biological evaluation of 177 Lu‐labeled GluDTPA‐cyclo(RGDfK) for integrin α ν β 3 receptor‐positive tumor targeting. Journal of Labelled Compounds and Radiopharmaceuticals 2012, 55 (1) , 10-17. https://doi.org/10.1002/jlcr.1944
    29. Kui Luo, Gang Liu, Wenchuan She, Qiaoying Wang, Gang Wang, Bin He, Hua Ai, Qiyong Gong, Bin Song, Zhongwei Gu. Gadolinium-labeled peptide dendrimers with controlled structures as potential magnetic resonance imaging contrast agents. Biomaterials 2011, 32 (31) , 7951-7960. https://doi.org/10.1016/j.biomaterials.2011.07.006
    30. Anna Lucia Tornesello, Michela Aurilio, Antonella Accardo, Laura Tarallo, Antonio Barbieri, Claudio Arra, Diego Tesauro, Giancarlo Morelli, Luigi Aloj. Gastrin and cholecystokinin peptide‐based radiopharmaceuticals: an in vivo and in vitro comparison. Journal of Peptide Science 2011, 17 (5) , 405-412. https://doi.org/10.1002/psc.1327
    31. Pol Besenius, Kelly P. van den Hout, Harald M. H. G. Albers, Tom F. A. de Greef, Luuk L. C. Olijve, Thomas M. Hermans, Bas F. M. de Waal, Paul H. H. Bomans, Nico A. J. M. Sommerdijk, Giuseppe Portale, Anja R. A. Palmans, Marcel H. P. van Genderen, Jef A. J. M. Vekemans, E. W. Meijer. Controlled Supramolecular Oligomerization of C 3 ‐Symmetrical Molecules in Water: The Impact of Hydrophobic Shielding. Chemistry – A European Journal 2011, 17 (18) , 5193-5203. https://doi.org/10.1002/chem.201002976
    32. Kui Luo, Gang Liu, Bin He, Yao Wu, Qingyong Gong, Bin Song, Hua Ai, Zhongwei Gu. Multifunctional gadolinium-based dendritic macromolecules as liver targeting imaging probes. Biomaterials 2011, 32 (10) , 2575-2585. https://doi.org/10.1016/j.biomaterials.2010.12.049
    33. Wenchuan SHE, Kui LUO, Bin HE, Hua AI, ZHongwei GU. FUNCTIONAL PEPTIDE DENDRIMERS AS MAGNETIC RESONANCE IMAGING PROBES. Acta Polymerica Sinica 2011, 011 (2) , 157-165. https://doi.org/10.3724/SP.J.1105.2011.10027
    34. Antonella Accardo, Anna Morisco, Eliana Gianolio, Diego Tesauro, Gaetano Mangiapia, Aurel Radulescu, Astrid Brandt, Giancarlo Morelli. Nanoparticles containing octreotide peptides and gadolinium complexes for MRI applications. Journal of Peptide Science 2011, 17 (2) , 154-162. https://doi.org/10.1002/psc.1308
    35. Luciano Lattuada, Alessandro Barge, Giancarlo Cravotto, Giovanni Battista Giovenzana, Lorenzo Tei. The synthesis and application of polyamino polycarboxylic bifunctional chelating agents. Chemical Society Reviews 2011, 40 (5) , 3019. https://doi.org/10.1039/c0cs00199f
    36. Giovanni B. Giovenzana, Daniela Imperio, Luciano Lattuada, Fulvio Uggeri. Stevens rearrangement as a tool for the structural modification of polyaminopolycarboxylic ligands. Organic & Biomolecular Chemistry 2011, 9 (3) , 679. https://doi.org/10.1039/c0ob00909a
    37. Dipti Kakkar, Anjani K. Tiwari, Krishna Chuttani, Ankur Kaul, Harpal Singh, Anil K. Mishra. Comparative Evaluation of Glutamate-Sensitive Radiopharmaceuticals: Technetium-99m–Glutamic Acid and Technetium-99m–Diethylenetriaminepentaacetic Acid–bis(Glutamate) Conjugate for Tumor Imaging. Cancer Biotherapy and Radiopharmaceuticals 2010, 25 (6) , 645-655. https://doi.org/10.1089/cbr.2010.0848
    38. Kui Luo, Gang Liu, Xiaowei Zhang, Wenchuan She, Bin He, Yu Nie, Li Li, Yao Wu, Zhirong Zhang, Qiyong Gong, Fabao Gao, Bin Song, Hua Ai, Zhongwei Gu. Functional L ‐Lysine Dendritic Macromolecules as Liver‐Imaging Probes. Macromolecular Bioscience 2009, 9 (12) , 1227-1236. https://doi.org/10.1002/mabi.200900231
    39. Giuseppe Gugliotta, Mauro Botta, Giovanni Battista Giovenzana, Lorenzo Tei. Fast and easy access to efficient bifunctional chelators for MRI applications. Bioorganic & Medicinal Chemistry Letters 2009, 19 (13) , 3442-3444. https://doi.org/10.1016/j.bmcl.2009.05.024
    40. Antonella Accardo, Diego Tesauro, Anna Morisco, Gaetano Mangiapia, Mauro Vaccaro, Eliana Gianolio, Richard K. Heenan, Luigi Paduano, Giancarlo Morelli. Micelles obtained by aggregation of gemini surfactants containing the CCK8 peptide and a gadolinium complex. JBIC Journal of Biological Inorganic Chemistry 2009, 14 (4) , 587-599. https://doi.org/10.1007/s00775-009-0472-1
    41. Anna Morisco, Antonella Accardo, Eliana Gianolio, Diego Tesauro, Ettore Benedetti, Giancarlo Morelli. Micelles derivatized with octreotide as potential target-selective contrast agents in MRI. Journal of Peptide Science 2009, 15 (3) , 242-250. https://doi.org/10.1002/psc.1087
    42. Mauro Vaccaro, Gaetano Mangiapia, Antonella Accardo, Diego Tesauro, Eliana Gianolio, Henrich Frielinghaus, Giancarlo Morelli, Luigi Paduano. Polymerized mixed aggregates containing gadolinium complex and CCK8 peptide. Colloid and Polymer Science 2008, 286 (14-15) , 1643-1652. https://doi.org/10.1007/s00396-008-1940-9
    43. Marouan Rami, Alessandro Cecchi, Jean‐Louis Montero, Alessio Innocenti, Daniela Vullo, Andrea Scozzafava, Jean‐Yves Winum, Claudiu T. Supuran. Carbonic Anhydrase Inhibitors: Design of Membrane‐Impermeant Copper(II) Complexes of DTPA‐, DOTA‐, and TETA‐Tailed Sulfonamides Targeting the Tumor‐Associated Transmembrane Isoform IX. ChemMedChem 2008, 3 (11) , 1780-1788. https://doi.org/10.1002/cmdc.200800267
    44. Antonella Accardo, Diego Tesauro, Luigi Del Pozzo, Gaetano Mangiapia, Luigi Paduano, Giancarlo Morelli. Micelles by self‐assembling peptide‐conjugate amphiphile: synthesis and structural characterization. Journal of Peptide Science 2008, 14 (8) , 903-910. https://doi.org/10.1002/psc.1024
    45. Georg Dirscherl, Burkhard König. The Use of Solid‐Phase Synthesis Techniques for the Preparation of Peptide–Metal Complex Conjugates. European Journal of Organic Chemistry 2008, 2008 (4) , 597-634. https://doi.org/10.1002/ejoc.200700787
    46. Alessandro Barge, Lorenzo Tei, Dharita Upadhyaya, Franco Fedeli, Lorena Beltrami, Rachele Stefanìa, Silvio Aime, Giancarlo Cravotto. Bifunctional ligands based on the DOTA-monoamide cage. Organic & Biomolecular Chemistry 2008, 6 (7) , 1176. https://doi.org/10.1039/b715844k
    47. Cyrille Richard, Bich-Thuy Doan, Jean-Claude Beloeil, Michel Bessodes, Éva Tóth, Daniel Scherman. Noncovalent Functionalization of Carbon Nanotubes with Amphiphilic Gd 3+ Chelates:  Toward Powerful T 1 and T 2 MRI Contrast Agents. Nano Letters 2008, 8 (1) , 232-236. https://doi.org/10.1021/nl072509z
    48. Mauro Vaccaro, Gaetano Mangiapia, Luigi Paduano, Eliana Gianolio, Antonella Accardo, Diego Tesauro, Giancarlo Morelli. Structural and Relaxometric Characterization of Peptide Aggregates Containing Gadolinium Complexes as Potential Selective Contrast Agents in MRI. ChemPhysChem 2007, 8 (17) , 2526-2538. https://doi.org/10.1002/cphc.200700505
    49. Mauro Vaccaro, Antonella Accardo, Gerardino D’Errico, Karin Schillén, Aurel Radulescu, Diego Tesauro, Giancarlo Morelli, Luigi Paduano. Peptides and Gd Complexes Containing Colloidal Assemblies as Tumor-Specific Contrast Agents in MRI: Physicochemical Characterization. Biophysical Journal 2007, 93 (5) , 1736-1746. https://doi.org/10.1529/biophysj.107.107417
    50. Elisa Battistini, Armando Mortillaro, Silvio Aime, Joop A. Peters. Molecular recognition of sugars by lanthanide (III) complexes of a conjugate of N, N ‐bis[2‐[bis[2‐(1, 1‐dimethylethoxy)‐2‐oxoethyl]amino]ethyl]glycine and phenylboronic acid. Contrast Media & Molecular Imaging 2007, 2 (4) , 163-171. https://doi.org/10.1002/cmmi.141
    51. Diego Tesauro, Antonella Accardo, Eliana Gianolio, Luigi Paduano, José Teixeira, Karin Schillén, Silvio Aime, Giancarlo Morelli. Peptide Derivatized Lamellar Aggregates as Target‐Specific MRI Contrast Agents. ChemBioChem 2007, 8 (8) , 950-955. https://doi.org/10.1002/cbic.200700077
    52. Alessandro Barge, Giancarlo Cravotto, Bruna Robaldo, Eliana Gianolio, Silvio Aime. New CD derivatives as self-assembling contrast agents for magnetic resonance imaging (MRI). Journal of Inclusion Phenomena and Macrocyclic Chemistry 2007, 57 (1-4) , 489-495. https://doi.org/10.1007/s10847-006-9239-2
    53. Tatjana N. Parac-Vogt, Luce Vander Elst, Kristof Kimpe, Sophie Laurent, Carmen Burtéa, Feng Chen, Rik Van Deun, Yicheng Ni, Robert N. Muller, Koen Binnemans. Pharmacokinetic andin vivo evaluation of a self-assembled gadolinium(III)-iron(II) contrast agent with high relaxivity. Contrast Media & Molecular Imaging 2006, 1 (6) , 267-278. https://doi.org/10.1002/cmmi.114
    54. Luciano Lattuada, Silvia Demattio, Veronica Vincenzi, Claudia Cabella, Massimo Visigalli, Silvio Aime, Simonetta Geninatti Crich, Eliana Gianolio. Magnetic resonance imaging of tumor cells by targeting the amino acid transport system. Bioorganic & Medicinal Chemistry Letters 2006, 16 (15) , 4111-4114. https://doi.org/10.1016/j.bmcl.2006.04.081
    55. Nathalie Mignet, Quentin le Masne de Chermont, Tatiana Randrianarivelo, Johanne Seguin, Cyrille Richard, Michel Bessodes, Daniel Scherman. Liposome biodistribution by time resolved fluorimetry of lipophilic europium complexes. European Biophysics Journal 2006, 35 (2) , 155-161. https://doi.org/10.1007/s00249-005-0008-8
    56. Radhakrishna Pillai, Edmund R. Marinelli, Rolf E. Swenson. A flexible method for preparation of peptide homo‐ and heterodimers functionalized with affinity probes, chelating ligands, and latent conjugating groups. Peptide Science 2006, 84 (6) , 576-585. https://doi.org/10.1002/bip.20570
    57. Luciano Lattuada, Milena Gabellini. Straightforward Synthesis of a Novel Maleimide‐DTPA Bifunctional Chelating Agent. Synthetic Communications 2005, 35 (18) , 2409-2413. https://doi.org/10.1080/00397910500189569
    58. Sander Langereis, Anouk Dirksen, Bas F. M. De Waal, Marcel H. P. Van Genderen, Quido G. De Lussanet, Tilman M. Hackeng, E. W. Meijer. Solid‐Phase Synthesis of a Cyclic NGR‐Functionalized Gd III DTPA Complex. European Journal of Organic Chemistry 2005, 2005 (12) , 2534-2538. https://doi.org/10.1002/ejoc.200500045
    59. Simonetta Geninatti Crich, Alessandro Barge, Elisa Battistini, Claudia Cabella, Sara Coluccia, Dario Longo, Valentina Mainero, Guido Tarone, Silvio Aime. Magnetic resonance imaging visualization of targeted cells by the internalization of supramolecular adducts formed between avidin and biotinylated Gd3+ chelates. JBIC Journal of Biological Inorganic Chemistry 2005, 10 (1) , 78-86. https://doi.org/10.1007/s00775-004-0616-2
    60. Gaetano Mangiapia, Antonella Accardo, Fabrizio Lo Celso, Diego Tesauro, Giancarlo Morelli, Aurel Radulescu, Luigi Paduano. Mixed Micelles Composed of Peptides and Gadolinium Complexes as Tumor-Specific Contrast Agents in MRI:  A SANS Study. The Journal of Physical Chemistry B 2004, 108 (45) , 17611-17617. https://doi.org/10.1021/jp048466h
    61. Tatjana N. Parac‐Vogt, Kristof Kimpe, Sophie Laurent, Corinne Piérart, Luce Vander Elst, Robert N. Muller, Koen Binnemans. Gadolinium DTPA‐Monoamide Complexes Incorporated into Mixed Micelles as Possible MRI Contrast Agents. European Journal of Inorganic Chemistry 2004, 2004 (17) , 3538-3543. https://doi.org/10.1002/ejic.200400187
    62. Pier Lucio Anelli, Luciano Lattuada, Vito Lorusso, Giovanna Lux, Alberto Morisetti, Pierfrancesco Morosini, Michele Serleti, Fulvio Uggeri. Conjugates of Gadolinium Complexes to Bile Acids as Hepatocyte-Directed Contrast Agents for Magnetic Resonance Imaging. Journal of Medicinal Chemistry 2004, 47 (14) , 3629-3641. https://doi.org/10.1021/jm0310683
    63. Sander Langereis, Quido G. de Lussanet, Marcel H. P. van Genderen, Walter H. Backes, E. W. Meijer. Multivalent Contrast Agents Based on Gadolinium−Diethylenetriaminepentaacetic Acid-Terminated Poly(propylene imine) Dendrimers for Magnetic Resonance Imaging. Macromolecules 2004, 37 (9) , 3084-3091. https://doi.org/10.1021/ma035983+
    64. Stefania De Luca, Giancarlo Morelli. Synthesis and characterization of a sulfated and a non‐sulfated cyclic CCK8 analogue functionalized with a chelating group for metal labelling. Journal of Peptide Science 2004, 10 (5) , 265-273. https://doi.org/10.1002/psc.527
    65. L. Aloj, M. Panico, C. Caraco, S. Del Vecchio, C. Arra, A. Affuso, A. Accardo, R. Mansi, D. Tesauro, S. De Luca, C. Pedone, R. Visentin, U. Mazzi, G. Morelli, M. Salvatore. In Vitro and In Vivo Characterization of Indium-111 and Technetium-99m Labeled CCK-8 Derivatives for CCK-B Receptor Imaging. Cancer Biotherapy and Radiopharmaceuticals 2004, 19 (1) , 93-98. https://doi.org/10.1089/108497804773391739
    66. Rosalba Mansi, Diego Tesauro, Antonia De Capua, Roberto Fattorusso, Corradina Caracò, Luigi Aloj, Ettore Benedetti, Giancarlo Morelli. Peptide-chelating agent conjugate for selective targeting of somatostatin receptor type 1: Synthesis and characterization. Biopolymers 2004, 76 (6) , 527-534. https://doi.org/10.1002/bip.20169
    67. Luciano Lattuada, Giovanna Lux. Synthesis of Gd-DTPA-cholesterol: a new lipophilic gadolinium complex as a potential MRI contrast agent. Tetrahedron Letters 2003, 44 (20) , 3893-3895. https://doi.org/10.1016/S0040-4039(03)00829-3
    68. John S. Davies, Loai Al‐Jamri. Synthesis of N α ‐Boc‐ N ε ‐tetrabenzyl‐DTPA‐ L ‐lysine and N α ‐Fmoc‐ N ε ‐tetra‐t‐butyl‐DTPA‐ L ‐lysine, building blocks for solid phase synthesis of DTPA‐containing peptides. Journal of Peptide Science 2002, 8 (12) , 663-670. https://doi.org/10.1002/psc.427
    69. L. Aloj, M. R. Panico, C. Caracó, A. Zannetti, S. Del Vecchio, C. Di Nuzzo, C. Arra, G. Morelli, D. Tesauro, S. De Luca, C. Pedone, M. Salvatore. Radiolabeling approaches for cholecystokinin B receptor imaging. Peptide Science 2002, 66 (6) , 370-380. https://doi.org/10.1002/bip.10347
    70. Pier Lucio Anelli, Luciano Lattuada, Vito Lorusso, Michael Schneider, Hervé Tournier, Fulvio Uggeri. Mixed micelles containing lipophilic gadolinium complexes as MRA contrast agents. Magma: Magnetic Resonance Materials in Physics, Biology, and Medicine 2001, 12 (2-3) , 114-120. https://doi.org/10.1007/BF02668092
    71. J. C. Amedio, G. Van Wagenen, G. Zavlin, Albert Gyorkos, S. A. Peterson. Preparation of N,N-Bis[2-[N',N'-Bis[(Tert-Butoxycarbonyl)Methyl]-Amino]Ethyl-L-Aspartic Acid: An Intermediate in the Synthesis of MRI Contrast Agents. Synthetic Communications 2000, 30 (20) , 3755-3763. https://doi.org/10.1080/00397910008087003
    72. Thomas J. Tolbert, Chi-Huey Wong. Intein-Mediated Synthesis of Proteins Containing Carbohydrates and Other Molecular Probes. Journal of the American Chemical Society 2000, 122 (23) , 5421-5428. https://doi.org/10.1021/ja0000192
    Download PDF

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect