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

Patent ·
OSTI ID:870922
 [1];  [1]
  1. Berkeley, CA
+ Show Author Affiliations

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 (United States)
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
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
Ferric ion sequestering agents. 14. 1-Hydroxy-2(1H)-pyridinone complexes: properties and structure of a novel iron-iron dimer journal November 1985
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

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Related Subjects

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