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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. 2 figs.

Inventors:
;
Issue Date:
Research Org.:
Univ. of California (United States)
Sponsoring Org.:
USDOE, Washington, DC (United States); National Insts. of Health, Bethesda, MD (United States); National Inst. of Environmental Health Sciences, Research Triangle Park, NC (United States)
OSTI Identifier:
335461
Patent Number(s):
5892029
Application Number:
PAN: 8-837,729; CNN: Grant AI 11744;Grant DK32999;Grant ES 02698; TRN: 99:004569
Assignee:
Univ. of California, Oakland, CA (United States)
DOE Contract Number:  
AC03-76SF00098
Resource Type:
Patent
Resource Relation:
Other Information: PBD: 6 Apr 1999
Country of Publication:
United States
Language:
English
Subject:
56 BIOLOGY AND MEDICINE, APPLIED STUDIES; CHELATING AGENTS; STABILITY; MOLECULAR STRUCTURE; PLUTONIUM; URANIUM; CHEMICAL BONDS; LIGANDS; RADIOSENSITIZERS

Citation Formats

Raymond, K, and Xu, J. 3-hydroxy-2(1H)-pyridinone chelating agents. United States: N. p., 1999. Web.
Raymond, K, & Xu, J. 3-hydroxy-2(1H)-pyridinone chelating agents. United States.
Raymond, K, and Xu, J. Tue . "3-hydroxy-2(1H)-pyridinone chelating agents". United States.
@article{osti_335461,
title = {3-hydroxy-2(1H)-pyridinone chelating agents},
author = {Raymond, K and Xu, J},
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. 2 figs.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1999},
month = {4}
}