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

Abstract

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 the 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 the 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. 2 figs.

Inventors:
;
Issue Date:
Research Org.:
University of California
OSTI Identifier:
504948
Patent Number(s):
5,624,901
Application Number:
PAN: 8-285,640; CNN: Grant AI 11744;Grant DK32999;Grant ES 02698
Assignee:
Univ. of California, Oakland, CA (United States)
DOE Contract Number:  
AC03-76SF00098
Resource Type:
Patent
Resource Relation:
Other Information: PBD: 29 Apr 1997
Country of Publication:
United States
Language:
English
Subject:
56 BIOLOGY AND MEDICINE, APPLIED STUDIES; CHELATING AGENTS; STRUCTURE-ACTIVITY RELATIONSHIPS; METALS; METABOLISM; ORAL ADMINISTRATION; INTRAPERITONEAL INJECTION

Citation Formats

Raymond, K N, and Xu, J. 3-hydroxy-2(1H)-pyridinone chelating agents. United States: N. p., 1997. Web.
Raymond, K N, & Xu, J. 3-hydroxy-2(1H)-pyridinone chelating agents. United States.
Raymond, K N, and Xu, J. Tue . "3-hydroxy-2(1H)-pyridinone chelating agents". United States.
@article{osti_504948,
title = {3-hydroxy-2(1H)-pyridinone chelating agents},
author = {Raymond, K N and Xu, J},
abstractNote = {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 the 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 the 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. 2 figs.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1997},
month = {4}
}