210366-17-9

Upstream product

• 210366-15-7 1-(benzyloxy)-2-oxo-1,2-dihydropyridine-6-carboxylic acid 
• 19621-92-2 6-Hydroxypicolinic acid 
• 94781-89-2 1,2-dihydro-1-hydroxy-2-oxopyridine-6-carboxylic acid 
• 210366-10-2 methyl-1-hydroxy-6-oxo-1,6-dihydropyridine-2-carboxylate 
• 210366-13-5 methyl 1-(benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxylate 
• 94781-88-1 6-bromopyridine-2-carboxylic acid-1-N-oxide 
• 21190-87-4 6-bromo-pyridine-2-carboxylic acid 
• 79-37-8 oxalyl dichloride 
• 19621-92-2 2-oxo-1,2-dihydropyridine-6-carboxylic acid 

Downstream Products

• 460986-08-7 3,4,3-LI-(1,2-HOPOBn) 
• 460986-10-1 3,4,3-LI-(1,2-Me-3,2-HOPO)Bn 
• 1001854-65-4 C₇₀H₈₀N₁₀O₁₂ 
• 1253698-21-3 C₇₁H₈₁N₁₁O₁₄ 
• 1001404-38-1 H(8O₂,2)-1,2-HOPOBn 
• 1297532-30-9 PEG-o-phen-Boc-1,2-HOPO(Bn) 
• 1297532-42-3 TAM(o-phen-1,2-HOPO)2 

Relevant academic research and scientific papers

Sequestering agents for uranyl chelation: new calixarene ligands

Synthesis of sulfocatecholamide (CAMS) and hydroxypyridinone (HOPO) calixarene ligands and determination of their binding abilities for the uranyl cation were described. Chelating properties were determined by UV spectrophotometry in aqueous media under v

EuIII complexes of octadentate 1-hydroxy-2-pyridinones: Stability and improved photophysical performance

The luminescence properties of lanthanoid ions can be dramatically enhanced by coupling them to antenna ligands that absorb light in the UV-visible and then efficiently transfer the energy to the lanthanoid centre. The synthesis and the complexation of Ln

The Ligand Cap Affects the Coordination Number but Not Necessarily the Affinity for Anions of Tris-Bidentate Europium Complexes

To evaluate the effect of ligand geometry on the coordination number, number of inner-sphere water molecules, and affinity for anions of the corresponding lanthanide complex, six tris-bidentate 1,2-hydroxypyridonate (HOPO) europium(III) complexes with different cap sizes were synthesized and characterized. Wider or more flexible ligand caps, such as in EuIII-TREN-Gly-HOPO and EuIII-3,3-Gly-HOPO, enable the formation of nine-coordinate europium(III) complexes bearing three inner-sphere water molecules. In contrast, smaller or more rigid caps, such as in EuIII-TREN-HOPO, EuIII-2,2-Li-HOPO, EuIII-3,3-Li-HOPO, and EuIII-2,2-Gly-HOPO, favor eight-coordinate europium(III) complexes that have only two inner-sphere water molecules. Notably, there is no correlation between the number of inner-sphere water molecules and the affinity of the Eu(III) complexes for phosphate. Some q = 2 (EuIII-TREN-HOPO, EuIII-3,3-Li-HOPO, and EuIII-2,2-Gly-HOPO) and some q = 3 (EuIII-TREN-Gly-HOPO) complexes have no affinity for anions, whereas one q = 2 complex (EuIII-2,2-Li-HOPO) and one q = 3 complex (EuIII-3,3-Gly-HOPO) have a high affinity for phosphate. For the latter two systems, each inner-sphere water molecule is replaced with a phosphate anion, resulting in the formation of EuLPi2 and EuLPi3 adducts, respectively.

IRON(III) AND GALLIUM(III) METAL ORGANIC POLYHEDRA, METHODS OF MAKING SAME, AND USES THEREOF

Compounds may have at least two structural units, which may be referred to as ligands. Each structural unit includes at least one spacer group and two or more donor groups. Compounds may have two or more iron(III) cations, one or more of which may be a hi

Combinatorial design of multimeric chelating peptoids for selective metal coordination

Current methods for metal chelation are generally based on multidentate organic ligands, which are generated through cumbersome multistep synthetic processes that lack flexibility for systematically varying metal-binding motifs. Octadentate ligands incorporating hydroxypyridinone or catecholamide binding moieties onto a spermine scaffold are known to display some of the highest affinities towards f-elements. Enhancing binding affinity for specific lanthanide or actinide ions however, necessitates ligand architectures that allow for modular and high throughput synthesis. Here we introduce a high-throughput combinatorial library of 16 tetrameric N-substituted glycine oligomers (peptoids) containing hydroxypyridinone or catecholamide chelating units linked via an ethylenediamine bridge and, for comparison, we also synthesized the corresponding mixed ligands derived from the spermine scaffold: 3,4,3-LI(1,2-HOPO)2(CAM)2 and 3,4,3-LI(CAM)2(1,2-HOPO)2. Coordination-based luminescence studies were carried out with Eu3+ and Tb3+ to begin probing the properties of the new ligand architecture and revealed higher sensitization efficiency with the spermine scaffold as well as different spectroscopic features among the structural peptoid isomers. Solution thermodynamic properties of selected ligands revealed different coordination properties between the spermine and peptoid analogues with Eu3+ stability constants log β110 ranging from 28.88 ± 3.45 to 43.97 ± 0.49. The general synthetic strategy presented here paves the way for precision design of new specific and versatile ligands, with a variety of applications tailored towards the use of f-elements, including separations, optical device optimization, and pharmaceutical development.

MACROCYCLIC LIGANDS WITH PENDANT CHELATING MOIETIES AND COMPLEXES THEREOF

The invention relates to chemical compounds and complexes that can be used in therapeutic and diagnostic applications.

COMPOSITIONS FOR THERAPEUTICS, TARGETED PET IMAGING AND METHODS OF THEIR USE

Described herein is a chelator for radiolabels (e.g., 89Zr) for targeted PET imaging that is an alternative to DFO. In certain embodiments, the chelator for 89Zr is the ligand, 3,4,3-(LI-1,2- HOPO) ("HOPO"), which exhibits equal or superior stability compared to DFO in chemical and biological assays across a period of several days in vivo. As shown in FIG. 1, the HOPO is an octadentate chelator that stabilizes chelation of radiolabels (e.g., 89Zr). A bifunctional ligand comprising p-SCN-Bn-HOPO is shown in FIG. 4 and FIG. 5. Such a bifunctional ligand can eliminate (e.g., 89Zr) loss from the chelate in vivo and reduce uptake in bone and non-target tissue. Therefore, the bifunctional HOPO ligand can facilitate safer and improved PET imaging with radiolabeled antibodies.

New insights into structure and luminescence of EuIII and SmIII complexes of the 3,4,3-LI(1,2-HOPO) ligand

We report the preparation and new insight into photophysical properties of luminescent hydroxypyridonate complexes [MIIIL]- (M = Eu or Sm) of the versatile 3,4,3-LI(1,2-HOPO) ligand (L). We report the crystal structure of this ligand

Alternative chelator for 89Zr radiopharmaceuticals: Radiolabeling and evaluation of 3,4,3-(LI-1,2-HOPO)

Zirconium-89 is an effective radionuclide for antibody-based positron emission tomography (PET) imaging because its physical half-life (78.41 h) matches the biological half-life of IgG antibodies. Desferrioxamine (DFO) is currently the preferred chelator for 89Zr4+; however, accumulation of 89Zr in the bones of mice suggests that 89Zr4+ is released from DFO in vivo. An improved chelator for 89Zr4+ could eliminate the release of osteophilic 89Zr4+ and lead to a safer PET tracer with reduced background radiation dose. Herein, we present an octadentate chelator 3,4,3-(LI-1,2-HOPO) (or HOPO) as a potentially superior alternative to DFO. The HOPO ligand formed a 1:1 Zr-HOPO complex that was evaluated experimentally and theoretically. The stability of 89Zr-HOPO matched or surpassed that of 89Zr-DFO in every experiment. In healthy mice, 89Zr-HOPO cleared the body rapidly with no signs of demetalation. Ultimately, HOPO has the potential to replace DFO as the chelator of choice for 89Zr-based PET imaging agents.

Hexadentate terephthalamide(bis-hydroxypyridinone) ligands for uranyl chelation: Structural and thermodynamic consequences of ligand variation (1)

Several linear, hexa- and tetradentate ligands incorporating a combination of 2,3-dihydroxy-terephthalamide (TAM) and hydroxypyridinone-amide (HOPO) moieties have been developed as uranyl chelating agents. Crystallographic analysis of several {UO2[TAM(HOPO)2]}2- complexes revealed a variable and crowded coordination geometry about the uranyl center. The TAM moiety dominates the bonding in hexadenate complexes, with linker rigidity dictating the equality of equatorial U-O bonding. Hexadentate TAM(HOPO)2 ligands demonstrated slow binding kinetics with uranyl affinities on average 6 orders of magnitude greater than those of similarly linked bis-HOPO ligands. Study of tetradentate TAM(HOPO) ligands revealed that the high uranyl affinity stems primarily from the presence of the TAM moiety and only marginally from increased ligand denticity. Uranyl affinities of TAM(HOPO)2 ligands were within experimental error, with TAM(o-phen-1,2-HOPO)2 exhibiting the most consistent uranyl affinity at variable pH.