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

Abstract

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.

Inventors:
 [1];  [1]
  1. Berkeley, CA
Issue Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
OSTI Identifier:
872243
Patent Number(s):
5892029
Assignee:
Regents of University of California (Oakland, CA)
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
DOE Contract Number:  
AC03-76SF00098
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
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; /999/

Citation Formats

Raymond, Kenneth, and Xu, Jide. 3-hydroxy-2(1H)-pyridinone chelating agents. United States: N. p., 1999. Web.
Raymond, Kenneth, & Xu, Jide. 3-hydroxy-2(1H)-pyridinone chelating agents. United States.
Raymond, Kenneth, and Xu, Jide. Fri . "3-hydroxy-2(1H)-pyridinone chelating agents". United States. https://www.osti.gov/servlets/purl/872243.
@article{osti_872243,
title = {3-hydroxy-2(1H)-pyridinone chelating agents},
author = {Raymond, Kenneth and Xu, Jide},
abstractNote = {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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1999},
month = {1}
}

Patent:

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