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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 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.

Inventors:
 [1];  [1]
  1. Berkeley, CA
Issue Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
OSTI Identifier:
870922
Patent Number(s):
5624901
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; 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/

Citation Formats

Raymond, Kenneth N, and Xu, Jide. 3-hydroxy-2(1H)-pyridinone chelating agents. United States: N. p., 1997. Web.
Raymond, Kenneth N, & Xu, Jide. 3-hydroxy-2(1H)-pyridinone chelating agents. United States.
Raymond, Kenneth N, and Xu, Jide. Wed . "3-hydroxy-2(1H)-pyridinone chelating agents". United States. https://www.osti.gov/servlets/purl/870922.
@article{osti_870922,
title = {3-hydroxy-2(1H)-pyridinone chelating agents},
author = {Raymond, Kenneth N and Xu, Jide},
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 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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1997},
month = {1}
}

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Works referenced in this record:

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