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3-hydroxy-2(1H)-pyridinone chelating agents

Patent ·
OSTI ID:870922
 [1];  [1]
  1. Berkeley, CA
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Disclosed is a series of improved metal chelating agents, which are highly effective upon both injection and oral administration; several of the most effective are of low toxicity. These chelating agents incorporate within their structure 1-hydroxy-2-pyridinone (1,2-HOPO) and 3-hydroxy-2-pyridinone (3,2-HOPO) moieties with a substituted carbamoyl group ortho to the hydroxy or oxo groups of the hydroxypyridinone ring. The electron-withdrawing carbamoyl group increases the acidity of the hydroxypyridinones. In the metal complexes of said chelating agents, the amide protons form very strong hydrogen bonds with its adjacent HOPO oxygen donor, making these complexes very stable at physiological conditions. The terminal N-substituents provides a certain degree of lipophilicity to said 3,2-HOPO, increasing oral activity. Also disclosed is a method of making the chelating agents and a method of producing a known compound, 3-hydroxy-1-alkyl-2(1H)pyridinone, used as a precursor to the chelating agent, safely and in large quantities.

Research Organization:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA
DOE Contract Number:
AC03-76SF00098
Assignee:
Regents of University of California (Oakland, CA)
Patent Number(s):
US 5624901
OSTI ID:
870922
Country of Publication:
United States
Language:
English

References (5)

Specific sequestering agents for the actinides. 21. Synthesis and initial biological testing of octadentate mixed catecholate-hydroxypyridinonate ligands journal February 1993
Specific Sequestering Agents for the Actinides. 28. Synthesis and Initial Evaluation of Multidentate 4-Carbamoyl-3-hydroxy-1-methyl-2(1H)-pyridinone Ligands for in Vivo Plutonium(IV) Chelation journal July 1995
Ferric ion sequestering agents. 14. 1-Hydroxy-2(1H)-pyridinone complexes: properties and structure of a novel iron-iron dimer journal November 1985
In Vivo Chelation of Am(III), Pu(IV), Np(V), and U(VI) in Mice by TREN-(Me-3,2-HOPO) journal May 1994
Novel 3-hydroxy-2(1H)-pyridinones. Synthesis, iron(III)-chelating properties and biological activity journal June 1990

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Related Subjects

-pyridinone
-pyridinone chelating
/514/530/999/
1-hydroxy-2-pyridinone
1h
2-hopo
3-hydroxy-1-alkyl-2
3-hydroxy-2
3-hydroxy-2-pyridinone
acidity
activity
adjacent
administration
agent
agents
agents disclosed
amide
bonds
carbamoyl
chelating
chelating agent
chelating agents
complexes
compound
conditions
degree
disclosed
donor
effective
electron-withdrawing
form
highly
highly effective
hopo
hydrogen
hydrogen bonds
hydroxy
hydroxypyridinone
hydroxypyridinones
improved
incorporate
increases
increasing
injection
lipophilicity
metal
metal chelating
metal complex
metal complexes
method
moieties
n-substituents
oral
oral administration
ortho
oxo
oxygen
physiological
physiological conditions
precursor
producing
protons
provides
pyridinone
quantities
safely
series
stable
strong
structure
substituted
terminal
toxicity