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

Patent · Fri Jan 01 00:00:00 EST 1999

OSTI ID:872243

Raymond, Kenneth ^[1]; Xu, Jide ^[1]

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1. Berkeley, CA

Disclosed is a series of improved chelating agents and the chelates formed from these 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 3-hydroxy-2-pyridinone (3,2-HOPO) moieties with a substituted carbamoyl group ortho to the hydroxy group of the hydroxypyridinone ring. The electron-withdrawing carbamoyl group increases the acidity, as well as the chemical stability towards oxidation and reduction, of the hydroxypyridinones. In the metal complexes of the chelating agents, the amide protons form very strong hydrogen bonds with the adjacent HOPO oxygen donor, making these complexes very stable at physiological conditions. The terminal N-substituents provide a certain degree of lipophilicity to the 3,2-HOPO, increasing oral activity.

• 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 5892029
• OSTI ID: 872243
• Country of Publication: United States
• Language: English

Related Subjects

3-hydroxy-2
1h
-pyridinone
chelating
agents
disclosed
series
improved
chelates
formed
highly
effective
injection
oral
administration
toxicity
incorporate
structure
3-hydroxy-2-pyridinone
2-hopo
moieties
substituted
carbamoyl
ortho
hydroxy
hydroxypyridinone
electron-withdrawing
increases
acidity
chemical
stability
towards
oxidation
reduction
hydroxypyridinones
metal
complexes
amide
protons
form
strong
hydrogen
bonds
adjacent
hopo
oxygen
donor
stable
physiological
conditions
terminal
n-substituents
provide
degree
lipophilicity
increasing
activity
chemical stability
metal complexes
chelating agents
chelating agent
highly effective
metal complex
physiological conditions
agents disclosed
-pyridinone chelating
oral administration
chelates form
chelates formed
hydrogen bonds
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