Bifunctional chelators for therapeutic lanthanide radiopharmaceuticals

Bioconjugate Chemistry

Volumn 12, Issue 1, 2001, Pages 7-34

  Liu, S ^a   Edwards, S D ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATION;

BI-FUNCTIONAL;

RARE EARTH ELEMENTS;

ANIMALIA;

EID: 0035155042     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc000070v     Document Type: Review

References (211)

1. Radionuclide therapy
2. Physical and biological targeting of radiotherapy
3. Towards the goal of cancer-specific imaging and therapy
4. Therapeutic radiopharmaceuticals
5. The role of inorganic chemistry in the development of radiometal agents for cancer therapy
6. Unsealed source therapy of painful bone metastases: An update
7. Current status of systemic intravenous radiopharmaceuticals for the treatment of painful metastatic bone diseases
8. Regulatory peptides receptors as molecular targets for cancer diagnosis and therapy
9. In vitro and in vivo evaluation of copper-64-octrotide conjugates
10. 3]octreotide, a promising somatostatin analogue for radionuclide therapy
11. Somatostatin analogues for somatostatin-receptor-mediated radiotherapy
12. DOTATOC: A powerful new tool for receptor-mediated radionuclide therapy
13. In vitro and in vivo evaluation of copper-64-octrotide conjugates
14. 3]octreotide as carriers for somatostatin receptor-targeted scintigraphy and radionuclide therapy
15. Response to treatment with yttrium-90-DOTA-Lanreotide of a patient with metastatic gastrinoma
16. Yttrium-90-labeled somatostatin-analogue for cancer treatment
17. 90Y]-Bz-DTPA-oct: A yttrium-90-labeled oactreotide analogue for radiotherapy of somatostatin receptor-positive tumors
18. 3]octreotide: Peptides for somatostatin receptor-targeted scintigraphy and radionuclide therapy
19. 90Y-SMT 487) eradicates experimental rat pancreatic CA 20948 tumours
20. 111In-labeled somatostatin analogues for tumor scintigraphy and radionuclide therapy
21. Unsulfated DTPA- and DOTA-CCK analogues as specific high affinity ligands for CCK-B receptor-expressing human and rat tissues in vitro and in vivo
22. 90Y-DOTATOC
23. 3]octreotide is dependent on the peptide amount
24. 3-octreotate. A new somatostatin analogue with improved target tissue uptake
25. 3-octreotate in a somatostatin receptor-positive, tumor-bearing rat model
26. Somatostatin receptor imaging and therapy of pancreatic endocrine tumors
27. Receptor nuclear medicine: Vasointestinal peptide and somatostatin receptor scintigraphy for diagnosis and treatment of tumour patients
28. 90Y-labeled analogue
29. Radiometal-labeled macrocyclic chelator-derived somatostatin analogue with superb tumor-targeting properties and potential for receptor-mediated internal therapy
30. Yttrium-90 DOTATOC: First clinical results
31. 3-octreotide (DOTATOC): A pilot study in human gliomas
32. Radiolabeled peptides for targeting cholecystokinin-B-gastrin receptor-expressing tumors
33. Cholecystokinin-B-gastrin receptor binding peptides: Preclinical development and evaluation of their diagnostic and therapeutic potential
34. Radionuclide production for biosciences
35. Reactor-produced radionuclides at the University of Missouri Research Reaction
36. RIAR reactor produced radionuclides
37. Reactor-produced radioisotopes from ORNL for bone pain palliation
38. Effects of linker chemistry on pharmacokinetics of radioimmunoconjugates
39. 90Y-labeled DOTA and maleimidocysteineamido-DOTA conjugated chimeric anticarcinoembryonic antigen antibody in xenograft-bearing nude mice: Comparison of stable and chemically labile linker systems
40. A novel bifunctional metabolizable linker for the conjugation of antibodies with radionuclides
41. Synthesis, biodistribution and renal handling of various chelate-somatostatin conjugates with metabolizable linking groups
42. A convenient and flexible approach for introducing linkers on bifunctional chelating agents
43. Synthesis, metal chelate stability studies, and enzyme digestion of a peptide-linked DOTA derivative and its corresponding radiolabeled immunoconjugates
44. Enzymatic cleavage of peptide-linked radiolabeles from immunoconjugates
45. Cathepsin substrate as cleavable linkers in bioconjugates, selected from a fluorescence quench combinatorial library
46. Potential technetium small molecule radiopharmaceuticals
47. 99mTc-labeled small peptides as diagnostic radiopharmaceuticals
48. Radiometal labeled agents (non-technetium) for diagnostic imaging
49. Copper radionuclides and radiopharmaceuticals in nuclear medicine
50. Criteria for the selection of the most desirable radionuclide for radiolabeling of monoclonal antibodies
51. The use of radionuclides for tumor therapy
52. Vehicles, chelators, and radionuclides: Choosing the "building blocks" of an effective therapeutic radioimmunoconjugate
53. Relation between the location of elements in the periodic table and various organ-uptake rates
54. Gadolinium(III) complex equilibria: The implications for Gd(III) MRI contrast agents
55. 3+ binding to model DTPA-conjugates and DTPA-proteins: Implications for their use as magnetic resonance contrast agents
56. n in mice
57. The relationship between thermodynamic and the toxicity of gadolinium complexes
58. Hepatobilliary and renal excretion in mice of charged and neutral gadolinium complexes of cyclic tetraaza-phosphinic and carboxylic acids
59. Paramagnetic metal complexes as water proton relaxation agents for NMR imaging: Theory and Design
60. Gadolinium(III) chelates as MRI contrast agents: Structure, dynamics, and applications
61. Synthesis of charged and uncharged complexes of gadolinium and yttrium with cyclic polyazaphosphinic acid ligands for in vivo applications
62. Synthesis of C- and N-functionalized derivatives of 1,4,7-triazacyclononane-1,4,7-triacetic acid (NOTA), 1,4,7,10-tetra-azacyclododecane-1,4,7,10-tetrayltetra-acetic acid (DOTA), and diethylenetriaminepenta-acetic acid (DTPA): Bifunctional complexing agents for the derivatization of antibodies
63. Structure and solution stability of indium and gallium complexes of 1,4,7-triazacyclononane-1,4,7-triacetic acid and yttrium complexes of 1,4,7,10-tetra-azacyclododecane-1,4,7,10-tetrayltetra-acetic acid and related ligands: Kinetically stable complexes for use in imaging and radioimmunotherapy
64. Stable anionic, neutral and cationic complexes of gadolinium with functionalized aminophosphinic acid macrocyclic ligands
65. The peptide way to macrocyclic bifunctional chelating agents: Synthesis of 2-(p-nitrobenzyl)-1,4,7,10-tetraazacyclododecane- N,N′,N″,N‴-tetraacetic acid and study of its yttrium(III) complex
66. III complexes
67. Physical parameters and biological stability of yttrium(III) diethylenetriaminepentaacetic acid derivative conjugates
68. Skeletal localization of samarium-153 chelates: Potential therapeutic bone agents
69. 153Sm radiotherapeutic bone agents
70. Relaometry, luminescence measurements, electronphorisis, and animal biodistribution of lanthanide(III) complexes of some polyaza macrocyclic acetates containing pyridine
71. Biodistribution of Sn 117m(4+)DTPA for palliative therapy of painful osseous metastasis
72. Thermodynamic and kinetic studies of lanthanide complexes of 1,4,7,10,13- pentaazacyclopentadecane-N,N′,N″,N‴,N″″ -pentaacetic acid and 1,4,7,10,13,16-hexaaza-cyclooctaadecane- N,N′,N″,N‴,N″″,N‴″-hexaaacetic acid
73. Synthesis and characterization of macrocyclic iron(III) sequestering agents
74. Iron(III) coordination chemistry of linear dihydroxyserine compounds derived from enterobactin
75. Structure and spectroscopic characterization of chiral ferric tris-catecholamides: Unraveling the design of enterobactin
76. Octahdral vs trigonal prismatic geometry in a series of catechol macrobicyclic ligand-metal complexes
77. III tris(catecholate) complexes effected by nonbonded, weakly polar interactions
78. Clinically useful chelators of tripositive elements
79. Iron chelating agents in medicine. The application of bidentate hydroxypyridin-4-ones
80. The aqueous coordination chemistry of aluminum
81. Novel tetrahydroxamate chelators for actinide complexation: Synthesis and binding studies
82. 153Sm]EDTMP: A potential therapy for bone cancer pain
83. 186Re-HEDP as bone therapeutic radiopharmaceuticals
84. Radiation dose distribution within the bone marrow of patients receiving holmiun-166 labeled phosphonate for marrow ablation
85. Pharmacokinetics, dosimetry and toxicity of holmiun-166-DOTMP for bone marrow ablation in multiple myeloma
86. Structure proof of syn/anti isomerism in N-alkylated diaminedithiol (DADT) complexes of technetium
87. 2 ligands: Synthesis and crystal structures
88. N,N′-Ethylene-di-l-cysteine (EC) complexes of Ga(III) and In(III): Molecular modeling, thermodynamic stability and in vivo studies
89. 3)
90. N,N′-Ethylenedi-L-cysteine (EC) and it metal complexes: Synthesis, characterization, crystal structures, and equalibrium constants
91. Indium(III) and gallium(III) complexes of bis(aminoethanethiol) ligands with different denticities: Stabilities, molecular modeling, and in vivo behavior
92. N,N′-Bis(2-mercaptoethyl)ethylenediamine-N,N′-diacetic acid; and effective ligand for indium(III)
93. The chelate, cryptate, and macrocyclic effects
94. Ligand design for selective complexation of metal ions in aqueous solution
95. Factors affecting stabilities of chelate, macrocyclic and macrobicyclic complexes in solution
96. Prediction of the coordination scheme of lanthanide N-tetrasubstituted tetraazamacrocycles: An X-ray crystallography and molecular modeling study
97. High yield synthesis of the enterobactin trilactone and evaluation of derivative siderophore analogues
98. 3+-binding and conformational properties of enterobactin
99. Chiral siderophore analogues: Enterobactin
100. Receptor mapping with artificial siderophores
101. Chiral siderophore analogues: Ferrioxamines and their iron(III) coordination properties
102. Chiral siderophore analogues: Ferrochrome
103. Synthetic receptors possessing noncovalent, macrocyclic rings
104. Tripodal peptides with chiral conformations stabilized by interstrand hydrogen bonds
105. 3 amine phenol ligands for group 13 Metal Ions: Evidence for intrastrand and interstrand hydrogen bonds in polydentate amine phenols
106. 3L = tris(((2′-hydroxy-3′-meth-oxybenzyl)-amino)ethyl)amine)
107. 3) tripodal amine phenol ligand complexes of aluminum, gallium and indium
108. 3) amine phenol ligands
109. 3 aminephenol ligands with phenolate oxygen bridges - Evidence for very weak magnetic exchange between lanthanide ions
110. 3-symmetrical lanthanide podates organized by intromolecular trifurcated hydrogen bonds
111. Selective binding of metal ions to macromolecules using bifunctional analogs of EDTA
112. Covalent attachment of chelating groups of macromolecules
113. Optimization of the DTPA mixed-anhydride reaction with antibodies at low concentration
114. 88Y complexes
115. Spectrophotometric method for the determination of a bifunctional DTPA ligand in DTPA-monoclonal antibody conjugates
116. 90Y radioimmunotherapy
117. Synthesis of 1-(p-isothiocyanatobenzyl) derivatives of DTPA and EDTA. Antibody labeling and tumor-imaging studies
118. Stereochemical influence on the stability of radio-metal complexes in vivo. Synthesis and evaluation of the four stereoisomers of 2-(p-nitrobenzyl)-trans-CyDTPA
119. Evaluation of the serum stability and in vivo biodistribution of CHX-DTPA and other ligands for yttrium labeling of monoclonal antibodies
120. A convenient synthesis of bifunctional chelating agents based on diethylenetriaminepentaacetic acid and their coordination chemistry with yttrium(III)
121. Synthesis of enantiometrically pure diethylenetriaminepentaacetic acid analogues. L-Phenylalanine as the educt for substitution at the central acetic acid
122. Cyclic polyethers and their complexes with metal salts
123. Synthetic methods in supermolecular chemistry
124. Complexes of polyaza macrocycles bearing pendent coordinating groups
125. Complexes of tridentate and pentadentate macrocyclic ligands
126. From mononuclear to polynuclear macrocyclic or macrocyclic complexes
127. Dinuclear metal complexes of bismacrocycles
128. Nitrogen analogs of crown ethers
129. A convenient synthesis of 1,4,7,10,13-pentaazacyclopentadecane
130. A new synthesis of cyclen (1,4,7,10-tetraazacyclododecane)
131. General routes for the synthesis of mono, di and tri-N-substituted derivatives of cyclam
132. Synthesis of nonionic gadolinium chelates useful as contrast agents for magnetic resonance imaging. 1,4,7-Tris(carboxymethyl)-10-substituted-1,4,7,10-tetraazacyclodo decane and their corresponding gadolinium chelates
133. Unexpected selectivity in the alkylation of polyazamacrocycles
134. Synthesis of new tetrakis N-substituted tetra-azamacrocycles
135. A convenient, novel approach for the synthesis of polyaza macrocyclic bifunctional chelating agents
136. 2NBn-TETA)]
137. Synthesis and evaluation of two new bifunctional carboxymethylated tetraazamacrocyclic chelating agents for protein labeling with indium-111
138. Carboxymethyl-substituted bifunctiona chelators: Preparation of aryl isothionate derivatives of 3-(carboxymethyl)-3-azapentanedioic acid, 3,12-bis(carboxymethyl)-6,9-dioxa-3,12- diazatetradecanedioic acid, and 1,4,7,10-tetraazacyclododecane-N,N′,N″,N‴-tetr aacetic acid for use as protein labels
139. General routes for the synthesis of mono N-alkylated derivatives of tetraazamacrocycles
140. Highly regioselective synthesis of 1,7-diprotected 1,4,7,10-tetraazacyclododecane derivatives
141. Efficient one-pot synthesis of JM3100
142. Stable anionic, neutral and cationic complexes of gadolinium with functionalized aminophosphinic acid macrocyclic ligands
143. Synthesis of C- and N-functionalized derivatives of 1,4,7-triazacyclononane-1,4,7-triacetic acid (NOTA), 1,4,7,10-tetra-azacyclododecane-1,4,7,10-tetrayltetra-acetic acid (DOTA), and diethylenetriaminepenta-acetic acid (DTPA): Bifunctional complexing agents for the derivatization of antibodies
144. Structure and solution stability of indium and gallium complexes of 1,4,7-triazacyclononane-1,4,7-triacetic acid and yttrium complexes of 1,4,7,10-tetra-azacyclododecane-1,4,7,10-tetrayltetra-acetic acid and related ligands: Kinetically stable complexes for use in imaging and radioimmunotherapy
145. Improved tumor targeting with recombinant antibody-macrocycle conjugates
146. Synthesis of new macrocyclic aminophosphinic acid complexing agents and their C- and P-functionalized derivatives for protein linkage
147. Metal chelates as probes of biological systems
148. Chelating agents for the binding of metal ions to antibodies
149. Copper chelates as probes of biological systems: Stable copper complexes with macrocyclic bifunctional chelating agent
150. Simplified method for conjugating macrocyclic bifunctional chelating agents to antibodies via 2-iminothiolane
151. Yttrium-90-labeled monoclonal antibody for therapy: Labeling by a new macrocyclic bifunctional chelating agent
152. The peptide way to macrocyclic bifunctional chelating agents: Synthesis of 2-(p-nitrobenzyl)-1,4,7,10-tetraazacyclododecane- N,N′,N″,N‴-tet-raacetic acid and study of its yttrium(III) complex
153. Antibody labeling with functionalized cyclam macrocycles
154. Implementation of macrocycle conjugated antibodies for tumor targeting
155. Towards tumor targeting with copper-radiolabeled macrocycle-antibody conjugates: Synthesis, antibody linkage, and complexation behaviour
156. 2NBn-TETA)
157. Convenient synthesis of bifunctional tetraaza macrocycles
158. Simplified synthesis of the bifunctional chelating agent 2-(4-aminobenzyl)-1,4,7,10-tetraazacyclododecane- N,N′,N″,N‴-tetraacetic acid
159. Pyramidal inversion
160. Gadolinium complexation by a new DTPA-amide ligand. Amide oxygen coordination
161. Neutral gadolinium(III) complexes of bulky octadentate dtpa derivatives as potential contrast agent for magnetic resonance imaging
162. The molecular structure of indium-DTPA
163. Solution structure and dynamics of lanthanide(III) complexes of diethylenetriaminepentaacetic acid: Two-dimensional NMR analysis
164. Multinuclear NMR study of lanthanide(III) complexes of diethylenetriaminepentaacetate
165. Non-ionic Ln(III) chelates as MRI contrast agents: Synthesis, characterization and 1H NMR relaxometric investigations of bis(benzylamide)-diethylenetriaminepentaacetic acid in aqueous solution Lu(III) and Gd(III) complexes
166. Multinuclear magnetic resonance study of the structure and dynamics of lanthanide(III) complexes of bis(proplamide) of diethylenetriaminepentaacetic acid in aqueous solution
167. 2+ by diethylenetriaminepentaacetic acid bis(methylamide)
168. Structure and dynamics of lanthanide(III) complexes of bis(proplamide) of diethylenetriaminepentaacetic acid in aqueous solution
169. Solution structure and dynamics of DTPA-Ln(III) complexes (DTPA = diethylene triamine penta acetate; Ln = La, Pr, and Eu)
170. Structures and dynamics of lanthanide(III) complexes of sugar-based DTPA-bis(amides) in aqueous solution: A multinuclear NMR study
171. 90Y-labeled DTPA-Biomolecule conjugates
172. Novel contrast agents for magnetic resonance imaging Synthesis and characterization of the ligand BOPTA and its Ln(III) complexes (Ln = Gd, La, Lu). X-Ray structure of disodium (TPS-9-145337286-C-S)-[4-carboxy-5,8,11-tris-(carboxymethyl)-1-ph enyl-2-oxa-5,8,11-triazatridecan-13-oato(5-)]gadolinate(2-) in a mixture with its enantiomer
173. Luminescence and NMR studies of the conformational isomers of lanthanide complexes with optically active polyaza polycarboxylic macrocycles
174. Structure and dynamics of all of the stereoisomers of europium complexes of tetra(carboxyethyl)derivatives of dota: Ring inversion is decoupled from cooperative arm rotation in the RRRR and RRRS isomers
175. Synthesis, characterization, and crystal structure of gadolinium(III) chelate of (1R, 4R, 7R)-α,α′,α″-trimethyl-1,4,7,10-tetr aazacyclododecane-1,4,7-triacetic acid (DO3MA)
176. 2O, and its relevance to NMR studies of the conformational behavior of the lanthanide complexes formed by the macrocyclic ligand DOTA
177. Synthesis, characterization, and crystal structures of M(DO3A) (M = Fe, Gd) and Na[(DOTA)] (M = Fe, Y, Gd)
178. Nuclear magnetic resonance spectroscopy of lanthanide complexes with tetraacetic tetraaza macrocycle. Unusual conformation properties
179. NMR study of solution structures and dynamics of lanthanide(III) complexes of DOTA
180. Synthesis, characterization, and 1/T1 NMRD profiles of gadolinium(III) complexes of monoamide derivatives of DOTA-like ligands. X-Ray structure of the 10-[2-[[2-hydroxy-1-(hydroxymethyl)-ethyl]amino]-1-(phenylmethoxy )methyl]2-oxoethyl]-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid-gadolinium(III) complex
181. Relaxometric, structural, and dynamic NMR studies of DOTA-like Ln(III) complexes (ln= La, Gd, Ho, Yb) containing a p-nitrophenyl substituent
182. MR imaging and spectroscopy applications of lanthanide complexes with macrocyclic phosphonate and phosphonate ester ligands
183. NMR studies of the lanthanide(III) complexes of 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrakis(methanephosphonic acid mono(2′,2′,2′-trifluoroethyl) ester)
184. Nuclear magnetic resonance, luminescence and structural studies of lanthanide complexes with oactadentate macrocyclic ligands bearing benzylphosphinate groups
185. Synthesis and characterization of the gadolinium(3+) complex of DOTA-propylamide: A model DOTA-protein conjugate
186. Preparation and characterization of paramagnetic polychelates and their protein conjugates
187. A facile, water soluble method for modification of proteins with DOTA. Use of elevated temperature and optimized pH to achieve high specific activity and high chelate stability in radiolabeled immunoconjugates
188. Maleimidocycteineamido-DOTA derivatives: New reagents for radiometal chelate conjugation to antibody sulfhydryl groups undergo pH-dependent cleavage reactions
189. Efficient multigram synthesis of the bifunctional chelating agent (S)-1-p-isothiocyanatobenzyl-diethylene-tetraaminepentaacetic acid
190. Pharmacokinetics of chimeric L6 conjugated to indium-111- and yttrium-90-peptide in tumor bearing mice
191. Yttrium-90 chelation properties of tetraazatetraacetic acid macrocycles, diethylenetriaminepentaacetic acid analogues, and a novel terpyridine acyclic chelator
192. Sammarium-153 and lutetium-177 chelation properties of selected macrocyclic and cyclic ligands
193. Equilibria and formation kinetics of some cyclen derivative complexes of lanthanide
194. 3+ macrocyclic complex
195. NMR studies of the metal loading kinetics and acid-base chemistry of DOTA and butylamide-DOTA
196. Metal complexes of cyclic tetra-azatetraacetic acids
197. Synthesis, stability, and structure of gadolinium(III) and yttrium(III) macrocyclic poly(amino carboxylates)
198. Equilibrium and kinetic studies of lanthanide complexes of macrocyclic polyamino carboxylates
199. Stabilities of the alkaline earth and divalent transition metal complexes of the tetraazamacrocyclic tetraacetic acid ligands
200. Stabilities of trivalenet metal ion complexes of the tetraacetate derivatives of 12-, 13-, and 14-membered tetraazamacrocycles
201. Optimized conditions for chelation of yttrium-90-DOTA immunoconjugates
202. Synthesis of nonionic gadolinium chelates useful as contrast agents for magnetic resonance imaging: 1,4,7,-Tris(carboxymethyl)-10-substituted-1,4,7,10-tetraazacyclod odecanes and their corresponding gadolinium chelates
203. 3+ complexes of macrocyclic polyamino carboxylates
204. Macrocyclic polyaminocarboxylate complexes of lanthanide as magnetic resonance imaging contrast agents
205. 2+ complexes of macrocyclic polyamino carboxylates
206. A kinetic investigation of the lanthanide DOTA chelates. Stability and rates of formation and dissociation of a macrocyclic gadolinium(III) polyaza polycarboxylaic MRI contrast agent
207. 90Y with 1,4,7,10-tetraazacy-clododecane-1,4,7,10-tetraacetic acid (DOTA), a model for cancer radioimmunotherapy